NPASS Compound

Structure

CID218841 OpenBabel06191716012D 30 34 0 0 1 0 0 0 0 0999 V2000 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4345 5.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6369 3.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 5.5388 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 2.4400 5.5170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0491 2.7298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8412 4.7080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0491 4.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 12 2 0 0 0 0 4 15 1 0 0 0 0 5 13 2 0 0 0 0 5 16 1 0 0 0 0 6 12 1 0 0 0 0 6 17 2 0 0 0 0 7 13 1 0 0 0 0 7 18 2 0 0 0 0 8 14 1 0 0 0 0 8 26 1 0 0 0 0 9 27 1 0 0 0 0 9 29 1 0 0 0 0 10 28 1 0 0 0 0 10 30 1 0 0 0 0 11 1 1 6 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 19 1 0 0 0 0 13 19 1 0 0 0 0 14 19 1 1 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 27 1 0 0 0 0 18 21 1 0 0 0 0 18 28 1 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 23 2 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.13
Volume:	398.152
LogP:	3.385
LogD:	3.38
LogS:	-5.132
# Rotatable Bonds:	5
TPSA:	81.68
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.691
Synthetic Accessibility Score:	3.724
Fsp3:	0.409
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:	-4.94
MDCK Permeability:	4.9577960453461856e-05
Pgp-inhibitor:	0.578
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	95.51860809326172%
Volume Distribution (VD):	3.915
Pgp-substrate:	2.53133225440979%

ADMET: Metabolism

CYP1A2-inhibitor:	0.515
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.97
CYP2C19-substrate:	0.792
CYP2C9-inhibitor:	0.888
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.91
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.974
CYP3A4-substrate:	0.834

ADMET: Excretion

Clearance (CL):	13.217
Half-life (T1/2):	0.132

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.224
Drug-inuced Liver Injury (DILI):	0.609
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.352
Skin Sensitization:	0.245
Carcinogencity:	0.855
Eye Corrosion:	0.003
Eye Irritation:	0.311
Respiratory Toxicity:	0.557

Download Data

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

Natural Product: NPC218841

Natural Product ID:	NPC218841
*Common Name:**	Peperomin A
IUPAC Name:	(3S,4S)-4-[bis(7-methoxy-1,3-benzodioxol-5-yl)methyl]-3-methyloxolan-2-one
Synonyms:
Standard InCHIKey:	UYKJDDXZIMXQNB-SMDDNHRTSA-N
Standard InCHI:	InChI=1S/C22H22O8/c1-11-14(8-26-22(11)23)19(12-4-15(24-2)20-17(6-12)27-9-29-20)13-5-16(25-3)21-18(7-13)28-10-30-21/h4-7,11,14,19H,8-10H2,1-3H3/t11-,14+/m0/s1
SMILES:	COc1cc(cc2c1OCO2)C([C@@H]1COC(=O)[C@H]1C)c1cc(OC)c2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL225191
PubChem CID:	11486787
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO28014	Garcinia gaudichaudii	Species	Clusiaceae	Eukaryota	n.a.	bark	n.a.	PMID[11101460]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14584959]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14643329]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	whole plant	Yunnan Province, China	2002-FEB	PMID[16309318]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	whole plant	Yunnan Province, China	2002-FEB	PMID[16724842]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548847]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27842	Gentiana makinoi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28014	Garcinia gaudichaudii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27842	Gentiana makinoi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28133	Geigeria filifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27439	Letharia vulpina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27842	Gentiana makinoi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13728	Metanarthecium luteoviride	Species	Nartheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22405	Litsea monopetala	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19590	Daedaleopsis tricolor	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16710	Pandanus tectorius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27718	Peperomia dindygulensis	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27184	Bonellia macrocarpa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27953	Eugenia formosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17271	Aegialitis annulata	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27401	Aniba riparia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27135	Tubularia larynx	Species	Tubulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27362	Hypericum elodes	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28066	Aloe speciosa	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28014	Garcinia gaudichaudii	Species	Clusiaceae	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
EC50	1
IC50	5
Others	11

Activity Type	# Activity
Cell Line	8
Organism	1
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	43200.0	nM	PMID[558394]
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	>	239000.0	nM	PMID[558395]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	239000.0	nM	PMID[558395]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	316000.0	nM	PMID[558395]
NPT116	Cell Line	HL-60	Homo sapiens	GI	=	17.0	%	PMID[558396]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	27.7	%	PMID[558396]
NPT165	Cell Line	HeLa	Homo sapiens	GI	<	5.0	%	PMID[558396]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	5300.0	nM	PMID[558394]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	8.2	n.a.	PMID[558394]
NPT27	Others	Unspecified		IC50	>	239000.0	nM	PMID[558395]
NPT2	Others	Unspecified		Activity	=	85.0	%	PMID[558395]
NPT2	Others	Unspecified		Activity	=	91.0	%	PMID[558395]
NPT2	Others	Unspecified		Activity	=	120.0	%	PMID[558395]
NPT2	Others	Unspecified		Activity	=	90.0	%	PMID[558395]
NPT2	Others	Unspecified		Activity	=	82.0	%	PMID[558395]
NPT2	Others	Unspecified		Activity	=	83.0	%	PMID[558395]

☑ 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 NPC218841 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	366
0.1-0.2	1439
0.2-0.3	3269
0.3-0.4	8475
0.4-0.5	10735
0.5-0.6	4612
0.6-0.7	9849
0.7-0.8	3491
0.8-0.85	275
0.85-0.9	120
0.9-0.95	52
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC92693
0.9855	High Similarity	NPC193779
0.9854	High Similarity	NPC177644
0.9854	High Similarity	NPC191158
0.9853	High Similarity	NPC151423
0.9853	High Similarity	NPC40237
0.971	High Similarity	NPC475000
0.9708	High Similarity	NPC210354
0.9708	High Similarity	NPC176586
0.951	High Similarity	NPC164082
0.9507	High Similarity	NPC177476
0.9507	High Similarity	NPC262455
0.9496	High Similarity	NPC474288
0.9412	High Similarity	NPC72796
0.9412	High Similarity	NPC44245
0.9371	High Similarity	NPC668
0.9371	High Similarity	NPC474965
0.9371	High Similarity	NPC174512
0.9371	High Similarity	NPC477695
0.9371	High Similarity	NPC293757
0.9371	High Similarity	NPC477698
0.9366	High Similarity	NPC65574
0.9366	High Similarity	NPC304687
0.9366	High Similarity	NPC101755
0.9366	High Similarity	NPC80230
0.9366	High Similarity	NPC104024
0.9343	High Similarity	NPC11453
0.9306	High Similarity	NPC149505
0.927	High Similarity	NPC211386
0.9241	High Similarity	NPC303519
0.9241	High Similarity	NPC477700
0.9241	High Similarity	NPC13985
0.9241	High Similarity	NPC210642
0.9236	High Similarity	NPC145569
0.9236	High Similarity	NPC216223
0.9225	High Similarity	NPC474158
0.9197	High Similarity	NPC19890
0.9197	High Similarity	NPC110958
0.9178	High Similarity	NPC56184
0.9178	High Similarity	NPC477699
0.9155	High Similarity	NPC477701
0.9155	High Similarity	NPC141569
0.9155	High Similarity	NPC166884
0.913	High Similarity	NPC148893
0.913	High Similarity	NPC49235
0.913	High Similarity	NPC25333
0.9124	High Similarity	NPC205915
0.911	High Similarity	NPC32079
0.9065	High Similarity	NPC143895
0.9058	High Similarity	NPC31530
0.9054	High Similarity	NPC273578
0.9054	High Similarity	NPC136757
0.9054	High Similarity	NPC178195
0.9054	High Similarity	NPC348849
0.9034	High Similarity	NPC40654
0.9034	High Similarity	NPC262804
0.9028	High Similarity	NPC3982
0.9014	High Similarity	NPC287124
0.9007	High Similarity	NPC96593
0.8993	High Similarity	NPC189474
0.8978	High Similarity	NPC192255
0.8951	High Similarity	NPC477697
0.8951	High Similarity	NPC470811
0.8951	High Similarity	NPC477696
0.8947	High Similarity	NPC288149
0.8936	High Similarity	NPC113550
0.8933	High Similarity	NPC32373
0.8933	High Similarity	NPC237946
0.8929	High Similarity	NPC230968
0.8929	High Similarity	NPC209229
0.8929	High Similarity	NPC102260
0.8926	High Similarity	NPC103197
0.8926	High Similarity	NPC30009
0.8913	High Similarity	NPC261812
0.8913	High Similarity	NPC72046
0.8913	High Similarity	NPC65183
0.8882	High Similarity	NPC470637
0.8874	High Similarity	NPC163527
0.8874	High Similarity	NPC207584
0.8874	High Similarity	NPC115281
0.8874	High Similarity	NPC19947
0.8874	High Similarity	NPC181168
0.8873	High Similarity	NPC56091
0.8873	High Similarity	NPC46591
0.8865	High Similarity	NPC14022
0.8851	High Similarity	NPC474975
0.8849	High Similarity	NPC266848
0.8849	High Similarity	NPC136750
0.8844	High Similarity	NPC125570
0.8828	High Similarity	NPC477702
0.8819	High Similarity	NPC106920
0.8819	High Similarity	NPC273657
0.8811	High Similarity	NPC312199
0.8811	High Similarity	NPC162851
0.8811	High Similarity	NPC218092
0.8811	High Similarity	NPC246474
0.8808	High Similarity	NPC473900
0.8794	High Similarity	NPC121651
0.8767	High Similarity	NPC321696
0.8767	High Similarity	NPC321958
0.8767	High Similarity	NPC212890
0.8767	High Similarity	NPC87295
0.8759	High Similarity	NPC143092
0.8759	High Similarity	NPC18211
0.8758	High Similarity	NPC268718
0.8758	High Similarity	NPC150943
0.8758	High Similarity	NPC91634
0.8758	High Similarity	NPC119910
0.8742	High Similarity	NPC234730
0.8742	High Similarity	NPC186316
0.8742	High Similarity	NPC254163
0.8733	High Similarity	NPC245948
0.8732	High Similarity	NPC283949
0.8723	High Similarity	NPC150534
0.8716	High Similarity	NPC85141
0.8705	High Similarity	NPC227160
0.8705	High Similarity	NPC82111
0.8701	High Similarity	NPC209411
0.8701	High Similarity	NPC152424
0.8701	High Similarity	NPC239890
0.8701	High Similarity	NPC100465
0.8701	High Similarity	NPC115624
0.8699	High Similarity	NPC327651
0.8699	High Similarity	NPC318286
0.8696	High Similarity	NPC476748
0.8693	High Similarity	NPC474043
0.869	High Similarity	NPC76415
0.869	High Similarity	NPC218510
0.869	High Similarity	NPC12728
0.869	High Similarity	NPC185071
0.8686	High Similarity	NPC223807
0.8681	High Similarity	NPC282291
0.8681	High Similarity	NPC166137
0.8667	High Similarity	NPC104353
0.8649	High Similarity	NPC304821
0.8645	High Similarity	NPC76687
0.8645	High Similarity	NPC61141
0.8633	High Similarity	NPC233224
0.8633	High Similarity	NPC271208
0.863	High Similarity	NPC326144
0.8623	High Similarity	NPC328682
0.8623	High Similarity	NPC281864
0.8623	High Similarity	NPC54321
0.8621	High Similarity	NPC474295
0.8611	High Similarity	NPC226547
0.8609	High Similarity	NPC473236
0.8609	High Similarity	NPC308555
0.8609	High Similarity	NPC474514
0.8601	High Similarity	NPC185908
0.859	High Similarity	NPC14294
0.859	High Similarity	NPC116759
0.8582	High Similarity	NPC1474
0.8581	High Similarity	NPC191352
0.8581	High Similarity	NPC258322
0.8571	High Similarity	NPC325122
0.8562	High Similarity	NPC477380
0.8562	High Similarity	NPC298317
0.8562	High Similarity	NPC255566
0.8551	High Similarity	NPC473092
0.8551	High Similarity	NPC8050
0.8551	High Similarity	NPC473093
0.8535	High Similarity	NPC222531
0.8533	High Similarity	NPC475170
0.8533	High Similarity	NPC158635
0.8533	High Similarity	NPC316989
0.8533	High Similarity	NPC473989
0.8533	High Similarity	NPC229882
0.8523	High Similarity	NPC477375
0.8523	High Similarity	NPC327352
0.8523	High Similarity	NPC252281
0.8523	High Similarity	NPC198129
0.8516	High Similarity	NPC474770
0.8511	High Similarity	NPC158526
0.8511	High Similarity	NPC129687
0.8511	High Similarity	NPC171928
0.8511	High Similarity	NPC16830
0.8511	High Similarity	NPC7744
0.8511	High Similarity	NPC33611
0.8511	High Similarity	NPC100223
0.8506	High Similarity	NPC477885
0.8503	High Similarity	NPC27159
0.8503	High Similarity	NPC474036
0.8503	High Similarity	NPC15743
0.8497	Intermediate Similarity	NPC238834
0.8493	Intermediate Similarity	NPC311057
0.8493	Intermediate Similarity	NPC52664
0.8489	Intermediate Similarity	NPC57119
0.8489	Intermediate Similarity	NPC226862
0.8489	Intermediate Similarity	NPC158471
0.8489	Intermediate Similarity	NPC165128
0.8489	Intermediate Similarity	NPC222127
0.8489	Intermediate Similarity	NPC82862
0.8483	Intermediate Similarity	NPC216434
0.8483	Intermediate Similarity	NPC103448
0.8483	Intermediate Similarity	NPC177868
0.8481	Intermediate Similarity	NPC306475
0.8477	Intermediate Similarity	NPC163002
0.8467	Intermediate Similarity	NPC477376
0.8467	Intermediate Similarity	NPC322426
0.8467	Intermediate Similarity	NPC477374

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 NPC218841 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	865
0.2-0.3	1711
0.3-0.4	2772
0.4-0.5	1882
0.5-0.6	1094
0.6-0.7	457
0.7-0.8	60
0.8-0.85	7
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8933	High Similarity	NPD4965	Approved
0.8933	High Similarity	NPD4967	Phase 2
0.8933	High Similarity	NPD4966	Approved
0.8816	High Similarity	NPD6234	Discontinued
0.8733	High Similarity	NPD37	Approved
0.8523	High Similarity	NPD6980	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7199	Phase 2
0.8428	Intermediate Similarity	NPD7228	Approved
0.8354	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD7240	Approved
0.82	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD3705	Approved
0.7964	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3818	Discontinued
0.7619	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD5494	Approved
0.7591	Intermediate Similarity	NPD5283	Phase 1
0.7578	Intermediate Similarity	NPD3817	Phase 2
0.7556	Intermediate Similarity	NPD7680	Approved
0.7552	Intermediate Similarity	NPD2981	Phase 2
0.7551	Intermediate Similarity	NPD3027	Phase 3
0.7532	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4110	Phase 3
0.7531	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD2982	Phase 2
0.75	Intermediate Similarity	NPD2438	Suspended
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5242	Approved
0.7465	Intermediate Similarity	NPD17	Approved
0.7423	Intermediate Similarity	NPD3882	Suspended
0.7415	Intermediate Similarity	NPD3018	Phase 2
0.741	Intermediate Similarity	NPD6232	Discontinued
0.7381	Intermediate Similarity	NPD7473	Discontinued
0.7365	Intermediate Similarity	NPD3926	Phase 2
0.7362	Intermediate Similarity	NPD5353	Approved
0.7353	Intermediate Similarity	NPD7074	Phase 3
0.7351	Intermediate Similarity	NPD6355	Discontinued
0.7333	Intermediate Similarity	NPD919	Approved
0.7329	Intermediate Similarity	NPD7028	Phase 2
0.7326	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1608	Approved
0.7294	Intermediate Similarity	NPD7054	Approved
0.7285	Intermediate Similarity	NPD2979	Phase 3
0.7267	Intermediate Similarity	NPD7685	Pre-registration
0.7254	Intermediate Similarity	NPD5536	Phase 2
0.7251	Intermediate Similarity	NPD7472	Approved
0.7241	Intermediate Similarity	NPD1281	Approved
0.7239	Intermediate Similarity	NPD1934	Approved
0.7237	Intermediate Similarity	NPD230	Phase 1
0.7237	Intermediate Similarity	NPD1933	Approved
0.7213	Intermediate Similarity	NPD5006	Approved
0.7213	Intermediate Similarity	NPD5005	Approved
0.7208	Intermediate Similarity	NPD3748	Approved
0.7205	Intermediate Similarity	NPD1653	Approved
0.7202	Intermediate Similarity	NPD7229	Phase 3
0.7195	Intermediate Similarity	NPD2801	Approved
0.7195	Intermediate Similarity	NPD1465	Phase 2
0.7195	Intermediate Similarity	NPD7819	Suspended
0.7193	Intermediate Similarity	NPD5844	Phase 1
0.7191	Intermediate Similarity	NPD7296	Approved
0.7179	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6386	Approved
0.7178	Intermediate Similarity	NPD6385	Approved
0.717	Intermediate Similarity	NPD6799	Approved
0.7168	Intermediate Similarity	NPD6559	Discontinued
0.7153	Intermediate Similarity	NPD5585	Approved
0.7152	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7808	Phase 3
0.7125	Intermediate Similarity	NPD2532	Approved
0.7125	Intermediate Similarity	NPD2534	Approved
0.7125	Intermediate Similarity	NPD2533	Approved
0.7117	Intermediate Similarity	NPD6599	Discontinued
0.7115	Intermediate Similarity	NPD7266	Discontinued
0.711	Intermediate Similarity	NPD6797	Phase 2
0.7095	Intermediate Similarity	NPD1283	Approved
0.7091	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD8455	Phase 2
0.7089	Intermediate Similarity	NPD4628	Phase 3
0.7089	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD4420	Approved
0.7081	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7251	Discontinued
0.7067	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4357	Discontinued
0.7059	Intermediate Similarity	NPD1613	Approved
0.7059	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7827	Phase 1
0.7051	Intermediate Similarity	NPD2796	Approved
0.7051	Intermediate Similarity	NPD2531	Phase 2
0.7044	Intermediate Similarity	NPD6190	Approved
0.7041	Intermediate Similarity	NPD1247	Approved
0.7041	Intermediate Similarity	NPD8127	Discontinued
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.7034	Intermediate Similarity	NPD1357	Approved
0.7034	Intermediate Similarity	NPD1651	Approved
0.702	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4908	Phase 1
0.7019	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3146	Approved
0.7018	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6166	Phase 2
0.7018	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7124	Phase 2
0.6993	Remote Similarity	NPD6233	Phase 2
0.6993	Remote Similarity	NPD8032	Phase 2
0.6988	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3750	Approved
0.6974	Remote Similarity	NPD7095	Approved
0.697	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7075	Discontinued
0.6948	Remote Similarity	NPD4060	Phase 1
0.6946	Remote Similarity	NPD5402	Approved
0.6943	Remote Similarity	NPD6099	Approved
0.6943	Remote Similarity	NPD6100	Approved
0.6943	Remote Similarity	NPD3539	Phase 1
0.6937	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD920	Approved
0.6933	Remote Similarity	NPD3266	Approved
0.6933	Remote Similarity	NPD3267	Approved
0.6933	Remote Similarity	NPD2797	Approved
0.6928	Remote Similarity	NPD1296	Phase 2
0.6928	Remote Similarity	NPD6801	Discontinued
0.6928	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7097	Phase 1
0.6923	Remote Similarity	NPD6111	Discontinued
0.6918	Remote Similarity	NPD6674	Discontinued
0.6918	Remote Similarity	NPD1243	Approved
0.6913	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4359	Approved
0.6908	Remote Similarity	NPD6832	Phase 2
0.6901	Remote Similarity	NPD5535	Approved
0.6901	Remote Similarity	NPD3787	Discontinued
0.6899	Remote Similarity	NPD6004	Phase 3
0.6899	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6005	Phase 3
0.6899	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3540	Phase 1
0.6899	Remote Similarity	NPD6002	Phase 3
0.6893	Remote Similarity	NPD7281	Phase 3
0.6893	Remote Similarity	NPD7280	Phase 3
0.6892	Remote Similarity	NPD1610	Phase 2
0.6883	Remote Similarity	NPD4062	Phase 3
0.6867	Remote Similarity	NPD7411	Suspended
0.6867	Remote Similarity	NPD6873	Phase 2
0.6864	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5958	Discontinued
0.6852	Remote Similarity	NPD1511	Approved
0.6849	Remote Similarity	NPD1894	Discontinued
0.6848	Remote Similarity	NPD7458	Discontinued
0.6845	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2935	Discontinued
0.6829	Remote Similarity	NPD5403	Approved
0.6826	Remote Similarity	NPD3382	Approved
0.6826	Remote Similarity	NPD3383	Approved
0.6826	Remote Similarity	NPD3384	Approved
0.6824	Remote Similarity	NPD3847	Discontinued
0.6818	Remote Similarity	NPD3764	Approved
0.6818	Remote Similarity	NPD3268	Approved
0.681	Remote Similarity	NPD5401	Approved
0.681	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4380	Phase 2
0.6805	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7768	Phase 2
0.6803	Remote Similarity	NPD5691	Approved
0.68	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD447	Suspended
0.6792	Remote Similarity	NPD1375	Discontinued
0.679	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4210	Discontinued
0.6786	Remote Similarity	NPD1358	Approved
0.6772	Remote Similarity	NPD7033	Discontinued
0.6772	Remote Similarity	NPD1510	Phase 2
0.6772	Remote Similarity	NPD2799	Discontinued
0.6768	Remote Similarity	NPD1512	Approved
0.6768	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6971	Discontinued
0.6755	Remote Similarity	NPD1876	Approved
0.6752	Remote Similarity	NPD6653	Approved
0.675	Remote Similarity	NPD4534	Discontinued
0.6747	Remote Similarity	NPD4005	Discontinued
0.6746	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1240	Approved
0.673	Remote Similarity	NPD1551	Phase 2
0.6714	Remote Similarity	NPD3134	Approved
0.671	Remote Similarity	NPD5109	Approved
0.671	Remote Similarity	NPD5110	Phase 2
0.671	Remote Similarity	NPD5111	Phase 2
0.6708	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7315	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