NPASS Compound

Structure

CID240305 OpenBabel06191716042D 34 36 0 0 0 0 0 0 0 0999 V2000 2.5279 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5836 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0557 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8156 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3291 -0.3561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7410 3.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7410 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8983 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0557 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8983 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7410 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0557 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8983 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7410 -0.9730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5836 0.4865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 2.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 0.4865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8983 3.4054 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 33 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 26 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 12 24 2 0 0 0 0 13 17 1 0 0 0 0 13 27 2 0 0 0 0 14 21 2 0 0 0 0 14 25 1 0 0 0 0 15 21 1 0 0 0 0 15 22 2 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 18 25 2 0 0 0 0 19 28 2 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 33 1 0 0 0 0 25 34 1 0 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.19
Volume:	479.176
LogP:	5.848
LogD:	2.56
LogS:	-3.618
# Rotatable Bonds:	6
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	3.436
Fsp3:	0.385
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:	-5.209
MDCK Permeability:	2.0508661691565067e-05
Pgp-inhibitor:	0.511
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.464
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	100.25304412841797%
Volume Distribution (VD):	0.291
Pgp-substrate:	1.3466509580612183%

ADMET: Metabolism

CYP1A2-inhibitor:	0.155
CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.139
CYP2C19-substrate:	0.39
CYP2C9-inhibitor:	0.764
CYP2C9-substrate:	0.803
CYP2D6-inhibitor:	0.158
CYP2D6-substrate:	0.187
CYP3A4-inhibitor:	0.243
CYP3A4-substrate:	0.465

ADMET: Excretion

Clearance (CL):	1.222
Half-life (T1/2):	0.129

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.296
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.122
Skin Sensitization:	0.93
Carcinogencity:	0.201
Eye Corrosion:	0.003
Eye Irritation:	0.788
Respiratory Toxicity:	0.221

Download Data

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

Natural Product: NPC240305

Natural Product ID:	NPC240305
*Common Name:**	Isobutyrylmallotochromene
IUPAC Name:	1-[6-[(3-acetyl-2,4-dihydroxy-6-methoxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl]-2-methylpropan-1-one
Synonyms:	isobutyrylmallotochromene
Standard InCHIKey:	BYAZINICHUCWIL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H30O8/c1-11(2)19(28)18-22(31)15(21(30)14-8-9-26(5,6)34-25(14)18)10-16-23(32)17(13(4)27)20(29)12(3)24(16)33-7/h8-9,11,29-32H,10H2,1-7H3
SMILES:	COc1c(Cc2c(O)c3C=CC(Oc3c(c2O)C(=O)C(C)C)(C)C)c(O)c(c(c1C)O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470674
PubChem CID:	189453
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
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800639]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[2347013]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3210017]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3734813]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4040956]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26880	Mallotus japonicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28265	Morus alba	Species	Moraceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.4	ug ml-1	PMID[463375]

☑ 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 NPC240305 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	365
0.1-0.2	1492
0.2-0.3	3848
0.3-0.4	10349
0.4-0.5	8708
0.5-0.6	4087
0.6-0.7	6165
0.7-0.8	4953
0.8-0.85	1593
0.85-0.9	776
0.9-0.95	353
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC254168
0.9925	High Similarity	NPC272844
0.9925	High Similarity	NPC248995
0.9562	High Similarity	NPC282300
0.9559	High Similarity	NPC217186
0.9559	High Similarity	NPC53181
0.9552	High Similarity	NPC101752
0.9493	High Similarity	NPC11561
0.9493	High Similarity	NPC226636
0.9489	High Similarity	NPC241100
0.9489	High Similarity	NPC150522
0.9489	High Similarity	NPC159275
0.9485	High Similarity	NPC268178
0.9485	High Similarity	NPC54820
0.9485	High Similarity	NPC180501
0.942	High Similarity	NPC205006
0.942	High Similarity	NPC147688
0.942	High Similarity	NPC110969
0.942	High Similarity	NPC103362
0.942	High Similarity	NPC156590
0.942	High Similarity	NPC64908
0.942	High Similarity	NPC118840
0.9416	High Similarity	NPC303633
0.9416	High Similarity	NPC18260
0.9416	High Similarity	NPC96565
0.9416	High Similarity	NPC220062
0.9416	High Similarity	NPC78913
0.9416	High Similarity	NPC55018
0.9416	High Similarity	NPC216978
0.9416	High Similarity	NPC472343
0.9416	High Similarity	NPC301217
0.9357	High Similarity	NPC469953
0.9357	High Similarity	NPC257236
0.9357	High Similarity	NPC131579
0.9357	High Similarity	NPC131568
0.9357	High Similarity	NPC234629
0.9357	High Similarity	NPC278175
0.9357	High Similarity	NPC311741
0.9353	High Similarity	NPC214236
0.9353	High Similarity	NPC62840
0.9353	High Similarity	NPC299080
0.9353	High Similarity	NPC217083
0.9353	High Similarity	NPC78803
0.9353	High Similarity	NPC59739
0.9353	High Similarity	NPC293852
0.9348	High Similarity	NPC475680
0.9348	High Similarity	NPC270883
0.9348	High Similarity	NPC305355
0.9348	High Similarity	NPC235239
0.9348	High Similarity	NPC172986
0.9348	High Similarity	NPC261227
0.9343	High Similarity	NPC470668
0.9343	High Similarity	NPC470669
0.9343	High Similarity	NPC201395
0.9328	High Similarity	NPC15834
0.9328	High Similarity	NPC215875
0.9291	High Similarity	NPC54577
0.9291	High Similarity	NPC111786
0.9291	High Similarity	NPC83357
0.9291	High Similarity	NPC246948
0.9291	High Similarity	NPC470647
0.9291	High Similarity	NPC475052
0.9291	High Similarity	NPC474161
0.9291	High Similarity	NPC67805
0.9291	High Similarity	NPC88964
0.9291	High Similarity	NPC301276
0.9291	High Similarity	NPC195621
0.9291	High Similarity	NPC477955
0.9291	High Similarity	NPC124729
0.9291	High Similarity	NPC476088
0.9291	High Similarity	NPC142405
0.9291	High Similarity	NPC214774
0.9291	High Similarity	NPC267375
0.9291	High Similarity	NPC176229
0.9291	High Similarity	NPC20488
0.9291	High Similarity	NPC312973
0.9291	High Similarity	NPC470322
0.9291	High Similarity	NPC127059
0.9291	High Similarity	NPC285630
0.9286	High Similarity	NPC166138
0.9286	High Similarity	NPC316816
0.9286	High Similarity	NPC219915
0.9286	High Similarity	NPC214166
0.9286	High Similarity	NPC18585
0.9286	High Similarity	NPC81697
0.9286	High Similarity	NPC94794
0.9286	High Similarity	NPC107177
0.9286	High Similarity	NPC196459
0.9286	High Similarity	NPC38219
0.9286	High Similarity	NPC223812
0.9286	High Similarity	NPC470296
0.9286	High Similarity	NPC77794
0.9286	High Similarity	NPC85162
0.9286	High Similarity	NPC125894
0.9286	High Similarity	NPC112791
0.9286	High Similarity	NPC278249
0.9286	High Similarity	NPC478086
0.9286	High Similarity	NPC188632
0.9286	High Similarity	NPC87609
0.9286	High Similarity	NPC106985
0.9281	High Similarity	NPC316911
0.9281	High Similarity	NPC110038
0.9281	High Similarity	NPC248372
0.9281	High Similarity	NPC470555
0.9281	High Similarity	NPC316560
0.9275	High Similarity	NPC23257
0.9259	High Similarity	NPC16197
0.9248	High Similarity	NPC186628
0.9231	High Similarity	NPC104236
0.9231	High Similarity	NPC164205
0.9225	High Similarity	NPC79469
0.9225	High Similarity	NPC23728
0.9225	High Similarity	NPC237635
0.9225	High Similarity	NPC97716
0.9225	High Similarity	NPC110303
0.9225	High Similarity	NPC283234
0.9225	High Similarity	NPC24673
0.9225	High Similarity	NPC249942
0.9225	High Similarity	NPC473077
0.9225	High Similarity	NPC104406
0.9225	High Similarity	NPC296998
0.9225	High Similarity	NPC297886
0.9225	High Similarity	NPC201731
0.922	High Similarity	NPC1886
0.922	High Similarity	NPC473015
0.922	High Similarity	NPC319752
0.922	High Similarity	NPC326500
0.922	High Similarity	NPC235217
0.922	High Similarity	NPC216538
0.922	High Similarity	NPC473014
0.922	High Similarity	NPC271288
0.922	High Similarity	NPC178627
0.922	High Similarity	NPC196137
0.922	High Similarity	NPC209040
0.922	High Similarity	NPC273538
0.922	High Similarity	NPC469935
0.922	High Similarity	NPC473013
0.9214	High Similarity	NPC144499
0.9214	High Similarity	NPC161506
0.9214	High Similarity	NPC166934
0.9214	High Similarity	NPC223500
0.9214	High Similarity	NPC266725
0.9214	High Similarity	NPC64915
0.9214	High Similarity	NPC200694
0.9214	High Similarity	NPC1089
0.9214	High Similarity	NPC37496
0.9214	High Similarity	NPC227579
0.9214	High Similarity	NPC32739
0.9214	High Similarity	NPC321148
0.9214	High Similarity	NPC324436
0.9214	High Similarity	NPC328164
0.9214	High Similarity	NPC324134
0.9214	High Similarity	NPC40833
0.9214	High Similarity	NPC306829
0.9214	High Similarity	NPC194432
0.9214	High Similarity	NPC265040
0.9214	High Similarity	NPC76338
0.9214	High Similarity	NPC167624
0.9214	High Similarity	NPC125855
0.9214	High Similarity	NPC296917
0.9214	High Similarity	NPC76372
0.9214	High Similarity	NPC228504
0.9214	High Similarity	NPC36181
0.9214	High Similarity	NPC148757
0.9214	High Similarity	NPC78
0.9214	High Similarity	NPC66515
0.9214	High Similarity	NPC166482
0.9214	High Similarity	NPC177354
0.9214	High Similarity	NPC10937
0.9214	High Similarity	NPC323884
0.9214	High Similarity	NPC220998
0.9214	High Similarity	NPC182852
0.9214	High Similarity	NPC321629
0.9214	High Similarity	NPC107572
0.9214	High Similarity	NPC326193
0.9209	High Similarity	NPC76445
0.9209	High Similarity	NPC284550
0.9209	High Similarity	NPC471587
0.9209	High Similarity	NPC129853
0.9209	High Similarity	NPC221173
0.9209	High Similarity	NPC69769
0.9203	High Similarity	NPC131130
0.9197	High Similarity	NPC234133
0.9197	High Similarity	NPC231772
0.9197	High Similarity	NPC47815
0.9197	High Similarity	NPC13408
0.9197	High Similarity	NPC174999
0.9197	High Similarity	NPC29353
0.9197	High Similarity	NPC194281
0.9197	High Similarity	NPC124784
0.9197	High Similarity	NPC161196
0.9197	High Similarity	NPC473887
0.9197	High Similarity	NPC127447
0.9191	High Similarity	NPC103842
0.9179	High Similarity	NPC279566
0.9167	High Similarity	NPC471115
0.9167	High Similarity	NPC29777
0.9161	High Similarity	NPC160821
0.9161	High Similarity	NPC189087
0.9161	High Similarity	NPC132592

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 NPC240305 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	992
0.2-0.3	1663
0.3-0.4	2718
0.4-0.5	1859
0.5-0.6	1095
0.6-0.7	349
0.7-0.8	110
0.8-0.85	26
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9357	High Similarity	NPD7410	Clinical (unspecified phase)
0.922	High Similarity	NPD4378	Clinical (unspecified phase)
0.8857	High Similarity	NPD1550	Clinical (unspecified phase)
0.8857	High Similarity	NPD1552	Clinical (unspecified phase)
0.8841	High Similarity	NPD6651	Approved
0.8794	High Similarity	NPD1549	Phase 2
0.8792	High Similarity	NPD8443	Clinical (unspecified phase)
0.8716	High Similarity	NPD7411	Suspended
0.8714	High Similarity	NPD1510	Phase 2
0.8696	High Similarity	NPD1240	Approved
0.8658	High Similarity	NPD6801	Discontinued
0.8652	High Similarity	NPD2796	Approved
0.8649	High Similarity	NPD4380	Phase 2
0.8601	High Similarity	NPD2800	Approved
0.86	High Similarity	NPD2393	Clinical (unspecified phase)
0.8571	High Similarity	NPD1607	Approved
0.8553	High Similarity	NPD7075	Discontinued
0.8477	Intermediate Similarity	NPD7819	Suspended
0.8367	Intermediate Similarity	NPD1511	Approved
0.8355	Intermediate Similarity	NPD2801	Approved
0.8355	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1934	Approved
0.8269	Intermediate Similarity	NPD6959	Discontinued
0.8255	Intermediate Similarity	NPD1512	Approved
0.8243	Intermediate Similarity	NPD6799	Approved
0.8228	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD3750	Approved
0.8151	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7768	Phase 2
0.8067	Intermediate Similarity	NPD2534	Approved
0.8067	Intermediate Similarity	NPD2532	Approved
0.8067	Intermediate Similarity	NPD2533	Approved
0.8065	Intermediate Similarity	NPD3817	Phase 2
0.8039	Intermediate Similarity	NPD6599	Discontinued
0.8028	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD3882	Suspended
0.8	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD5124	Phase 1
0.7973	Intermediate Similarity	NPD1243	Approved
0.7962	Intermediate Similarity	NPD3749	Approved
0.7961	Intermediate Similarity	NPD920	Approved
0.7961	Intermediate Similarity	NPD5403	Approved
0.795	Intermediate Similarity	NPD7473	Discontinued
0.7945	Intermediate Similarity	NPD2799	Discontinued
0.7902	Intermediate Similarity	NPD2313	Discontinued
0.7901	Intermediate Similarity	NPD3818	Discontinued
0.7891	Intermediate Similarity	NPD1551	Phase 2
0.7891	Intermediate Similarity	NPD2935	Discontinued
0.7875	Intermediate Similarity	NPD6232	Discontinued
0.7866	Intermediate Similarity	NPD5953	Discontinued
0.7862	Intermediate Similarity	NPD5494	Approved
0.7853	Intermediate Similarity	NPD7286	Phase 2
0.7853	Intermediate Similarity	NPD7054	Approved
0.7829	Intermediate Similarity	NPD5401	Approved
0.7823	Intermediate Similarity	NPD3748	Approved
0.7815	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7074	Phase 3
0.7805	Intermediate Similarity	NPD7472	Approved
0.7778	Intermediate Similarity	NPD3268	Approved
0.7778	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD6099	Approved
0.777	Intermediate Similarity	NPD6100	Approved
0.7758	Intermediate Similarity	NPD6797	Phase 2
0.7718	Intermediate Similarity	NPD2344	Approved
0.7712	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6559	Discontinued
0.7711	Intermediate Similarity	NPD7251	Discontinued
0.7703	Intermediate Similarity	NPD7033	Discontinued
0.7682	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1203	Approved
0.7676	Intermediate Similarity	NPD2797	Approved
0.7673	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7808	Phase 3
0.7639	Intermediate Similarity	NPD4908	Phase 1
0.7639	Intermediate Similarity	NPD6832	Phase 2
0.7628	Intermediate Similarity	NPD3226	Approved
0.7622	Intermediate Similarity	NPD2798	Approved
0.761	Intermediate Similarity	NPD5402	Approved
0.7609	Intermediate Similarity	NPD1548	Phase 1
0.7584	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7390	Discontinued
0.7529	Intermediate Similarity	NPD4360	Phase 2
0.7529	Intermediate Similarity	NPD4363	Phase 3
0.7518	Intermediate Similarity	NPD422	Phase 1
0.7518	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1610	Phase 2
0.7516	Intermediate Similarity	NPD2309	Approved
0.7486	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4361	Phase 2
0.7483	Intermediate Similarity	NPD2346	Discontinued
0.7469	Intermediate Similarity	NPD919	Approved
0.7467	Intermediate Similarity	NPD4308	Phase 3
0.7465	Intermediate Similarity	NPD9717	Approved
0.7451	Intermediate Similarity	NPD4628	Phase 3
0.7443	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5710	Approved
0.7439	Intermediate Similarity	NPD5711	Approved
0.7432	Intermediate Similarity	NPD943	Approved
0.7431	Intermediate Similarity	NPD3267	Approved
0.7431	Intermediate Similarity	NPD3266	Approved
0.7425	Intermediate Similarity	NPD5844	Phase 1
0.7421	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3926	Phase 2
0.7386	Intermediate Similarity	NPD2654	Approved
0.7381	Intermediate Similarity	NPD1729	Discontinued
0.7378	Intermediate Similarity	NPD1247	Approved
0.7361	Intermediate Similarity	NPD3225	Approved
0.7347	Intermediate Similarity	NPD4625	Phase 3
0.7329	Intermediate Similarity	NPD1465	Phase 2
0.7278	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6585	Discontinued
0.7235	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3972	Approved
0.7222	Intermediate Similarity	NPD1608	Approved
0.7205	Intermediate Similarity	NPD5889	Approved
0.7205	Intermediate Similarity	NPD5890	Approved
0.72	Intermediate Similarity	NPD4307	Phase 2
0.7188	Intermediate Similarity	NPD7458	Discontinued
0.7181	Intermediate Similarity	NPD1296	Phase 2
0.7178	Intermediate Similarity	NPD4288	Approved
0.7174	Intermediate Similarity	NPD7584	Approved
0.7172	Intermediate Similarity	NPD4749	Approved
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7119	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7003	Approved
0.7113	Intermediate Similarity	NPD9545	Approved
0.7107	Intermediate Similarity	NPD5049	Phase 3
0.7102	Intermediate Similarity	NPD4287	Approved
0.7093	Intermediate Similarity	NPD6104	Discontinued
0.7092	Intermediate Similarity	NPD9493	Approved
0.7081	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5408	Approved
0.7078	Intermediate Similarity	NPD5405	Approved
0.7078	Intermediate Similarity	NPD5406	Approved
0.7078	Intermediate Similarity	NPD5404	Approved
0.7067	Intermediate Similarity	NPD3764	Approved
0.7067	Intermediate Similarity	NPD6798	Discontinued
0.7067	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7199	Phase 2
0.7047	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1201	Approved
0.7014	Intermediate Similarity	NPD17	Approved
0.7011	Intermediate Similarity	NPD8313	Approved
0.7011	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD1241	Discontinued
0.6989	Remote Similarity	NPD8434	Phase 2
0.6982	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1613	Approved
0.697	Remote Similarity	NPD2296	Approved
0.6962	Remote Similarity	NPD2354	Approved
0.6959	Remote Similarity	NPD1470	Approved
0.6959	Remote Similarity	NPD1164	Approved
0.6959	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD411	Approved
0.6951	Remote Similarity	NPD7577	Discontinued
0.6944	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD447	Suspended
0.6928	Remote Similarity	NPD6355	Discontinued
0.6928	Remote Similarity	NPD230	Phase 1
0.6923	Remote Similarity	NPD6005	Phase 3
0.6923	Remote Similarity	NPD6002	Phase 3
0.6923	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1471	Phase 3
0.6923	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6004	Phase 3
0.6913	Remote Similarity	NPD1019	Discontinued
0.6909	Remote Similarity	NPD5761	Phase 2
0.6909	Remote Similarity	NPD5760	Phase 2
0.6892	Remote Similarity	NPD1876	Approved
0.6879	Remote Similarity	NPD2424	Discontinued
0.6875	Remote Similarity	NPD1894	Discontinued
0.6875	Remote Similarity	NPD7212	Phase 2
0.6875	Remote Similarity	NPD7213	Phase 3
0.6871	Remote Similarity	NPD1481	Phase 2
0.6867	Remote Similarity	NPD2861	Phase 2
0.6863	Remote Similarity	NPD4060	Phase 1
0.686	Remote Similarity	NPD3751	Discontinued
0.686	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4476	Approved
0.6859	Remote Similarity	NPD4477	Approved
0.6855	Remote Similarity	NPD3295	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