NPASS Compound

Structure

CID218092 OpenBabel06191716012D 26 31 0 0 1 0 0 0 0 0999 V2000 -0.5296 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -3.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -5.6654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -1.0827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -2.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 -1.1215 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 -3.2127 -4.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2127 -2.7737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6776 -4.7518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2764 -5.5608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 10 1 0 0 0 0 2 14 1 0 0 0 0 3 11 1 0 0 0 0 4 10 2 0 0 0 0 4 15 1 0 0 0 0 5 11 2 0 0 0 0 5 16 1 0 0 0 0 6 13 2 0 0 0 0 6 17 1 0 0 0 0 7 12 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 8 24 1 0 0 0 0 9 25 1 0 0 0 0 9 26 1 0 0 0 0 11 13 1 0 0 0 0 12 3 1 6 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 16 17 2 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 10 1 6 0 0 0 18 19 1 0 0 0 0 19 20 1 1 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.09
Volume:	337.424
LogP:	3.588
LogD:	2.82
LogS:	-5.183
# Rotatable Bonds:	1
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.735
Synthetic Accessibility Score:	3.606
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.059
MDCK Permeability:	4.009394979220815e-05
Pgp-inhibitor:	0.104
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.296
Plasma Protein Binding (PPB):	97.47940826416016%
Volume Distribution (VD):	2.51
Pgp-substrate:	2.177173376083374%

ADMET: Metabolism

CYP1A2-inhibitor:	0.785
CYP1A2-substrate:	0.694
CYP2C19-inhibitor:	0.98
CYP2C19-substrate:	0.351
CYP2C9-inhibitor:	0.89
CYP2C9-substrate:	0.864
CYP2D6-inhibitor:	0.946
CYP2D6-substrate:	0.891
CYP3A4-inhibitor:	0.963
CYP3A4-substrate:	0.802

ADMET: Excretion

Clearance (CL):	17.88
Half-life (T1/2):	0.098

ADMET: Toxicity

hERG Blockers:	0.111
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.5
Rat Oral Acute Toxicity:	0.105
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.093
Carcinogencity:	0.845
Eye Corrosion:	0.003
Eye Irritation:	0.189
Respiratory Toxicity:	0.783

Download Data

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

Natural Product: NPC218092

Natural Product ID:	NPC218092
*Common Name:**	(5S,5Ar,8Ar)-5-(1,3-Benzodioxol-5-Yl)-5A,8,8A,9-Tetrahydro-5H-[2]Benzofuro[5,6-F][1,3]Benzodioxol-6-One
IUPAC Name:	(5S,5aR,8aR)-5-(1,3-benzodioxol-5-yl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one
Synonyms:
Standard InCHIKey:	SCTKDFCQZSBHEE-NXXSPTCGSA-N
Standard InCHI:	InChI=1S/C20H16O6/c21-20-19-12(7-22-20)3-11-5-16-17(26-9-25-16)6-13(11)18(19)10-1-2-14-15(4-10)24-8-23-14/h1-2,4-6,12,18-19H,3,7-9H2/t12-,18-,19-/m0/s1
SMILES:	c1cc2c(cc1[C@H]1c3cc4c(cc3C[C@H]3COC(=O)[C@H]13)OCO4)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1976899
PubChem CID:	386603
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones

*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
NPO9031	Euonymus europaeus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9031	Euonymus europaeus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1040	Ficus conraui	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO617	Vicia balansae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9031	Euonymus europaeus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO103	Stereocaulon salazinum	Species	Stereocaulaceae	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
GI50	44

Activity Type	# Activity
Cell Line	44

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	21928.05	nM	PMID[478446]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	12022.64	nM	PMID[478446]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	15595.53	nM	PMID[478446]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	10616.96	nM	PMID[478446]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	16032.45	nM	PMID[478446]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	11994.99	nM	PMID[478446]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	4111.5	nM	PMID[478446]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	24660.39	nM	PMID[478446]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	9332.54	nM	PMID[478446]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	22698.65	nM	PMID[478446]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	24043.63	nM	PMID[478446]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	13867.56	nM	PMID[478446]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	18238.96	nM	PMID[478446]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	10990.06	nM	PMID[478446]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	24210.29	nM	PMID[478446]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	13273.94	nM	PMID[478446]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	24717.24	nM	PMID[478446]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	24099.05	nM	PMID[478446]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[478446]

☑ 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 NPC218092 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	385
0.1-0.2	1465
0.2-0.3	2944
0.3-0.4	8063
0.4-0.5	11308
0.5-0.6	5085
0.6-0.7	11443
0.7-0.8	1766
0.8-0.85	167
0.85-0.9	52
0.9-0.95	14
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC162851
1.0	High Similarity	NPC246474
0.9549	High Similarity	NPC19890
0.9549	High Similarity	NPC110958
0.9328	High Similarity	NPC205915
0.9296	High Similarity	NPC177476
0.9296	High Similarity	NPC262455
0.9265	High Similarity	NPC230968
0.9265	High Similarity	NPC102260
0.9225	High Similarity	NPC181464
0.9161	High Similarity	NPC24193
0.9155	High Similarity	NPC65574
0.9155	High Similarity	NPC80230
0.9155	High Similarity	NPC304687
0.9155	High Similarity	NPC101755
0.9155	High Similarity	NPC104024
0.9028	High Similarity	NPC127827
0.8966	High Similarity	NPC149505
0.8966	High Similarity	NPC475722
0.8944	High Similarity	NPC177644
0.8944	High Similarity	NPC191158
0.8904	High Similarity	NPC210642
0.8904	High Similarity	NPC13985
0.8881	High Similarity	NPC177167
0.8881	High Similarity	NPC223807
0.8865	High Similarity	NPC166137
0.8865	High Similarity	NPC282291
0.8865	High Similarity	NPC29599
0.8851	High Similarity	NPC54179
0.8819	High Similarity	NPC3982
0.8811	High Similarity	NPC92693
0.8811	High Similarity	NPC218841
0.8808	High Similarity	NPC470637
0.8808	High Similarity	NPC96593
0.8803	High Similarity	NPC176586
0.8803	High Similarity	NPC210354
0.875	High Similarity	NPC476748
0.875	High Similarity	NPC288149
0.8741	High Similarity	NPC86455
0.8741	High Similarity	NPC137920
0.8741	High Similarity	NPC125134
0.8731	High Similarity	NPC17348
0.8725	High Similarity	NPC273578
0.8725	High Similarity	NPC30009
0.8725	High Similarity	NPC103197
0.8699	High Similarity	NPC40654
0.8699	High Similarity	NPC262804
0.869	High Similarity	NPC193779
0.8675	High Similarity	NPC19600
0.8671	High Similarity	NPC40237
0.8671	High Similarity	NPC151423
0.8652	High Similarity	NPC14022
0.8609	High Similarity	NPC473900
0.8609	High Similarity	NPC32373
0.8609	High Similarity	NPC115123
0.8609	High Similarity	NPC239113
0.8609	High Similarity	NPC237946
0.8603	High Similarity	NPC158737
0.8601	High Similarity	NPC323601
0.8553	High Similarity	NPC181168
0.8553	High Similarity	NPC115281
0.8553	High Similarity	NPC163527
0.8553	High Similarity	NPC19947
0.8553	High Similarity	NPC207584
0.8552	High Similarity	NPC475000
0.8543	High Similarity	NPC234730
0.8506	High Similarity	NPC15212
0.8483	Intermediate Similarity	NPC474288
0.8452	Intermediate Similarity	NPC198796
0.8442	Intermediate Similarity	NPC119910
0.8442	Intermediate Similarity	NPC150943
0.8442	Intermediate Similarity	NPC78944
0.8442	Intermediate Similarity	NPC91634
0.8442	Intermediate Similarity	NPC268718
0.844	Intermediate Similarity	NPC176814
0.844	Intermediate Similarity	NPC68779
0.844	Intermediate Similarity	NPC300776
0.844	Intermediate Similarity	NPC5310
0.844	Intermediate Similarity	NPC4982
0.8433	Intermediate Similarity	NPC80241
0.8433	Intermediate Similarity	NPC301641
0.8425	Intermediate Similarity	NPC474036
0.8421	Intermediate Similarity	NPC186316
0.8417	Intermediate Similarity	NPC271208
0.8417	Intermediate Similarity	NPC134764
0.8417	Intermediate Similarity	NPC233224
0.8417	Intermediate Similarity	NPC171550
0.8414	Intermediate Similarity	NPC52664
0.8411	Intermediate Similarity	NPC245948
0.84	Intermediate Similarity	NPC164082
0.84	Intermediate Similarity	NPC303519
0.8392	Intermediate Similarity	NPC231719
0.8392	Intermediate Similarity	NPC52968
0.8389	Intermediate Similarity	NPC145569
0.8389	Intermediate Similarity	NPC216223
0.8387	Intermediate Similarity	NPC115624
0.8387	Intermediate Similarity	NPC239890
0.8387	Intermediate Similarity	NPC100465
0.8387	Intermediate Similarity	NPC209411
0.8387	Intermediate Similarity	NPC152424
0.838	Intermediate Similarity	NPC211386
0.838	Intermediate Similarity	NPC474139
0.8377	Intermediate Similarity	NPC474043
0.8357	Intermediate Similarity	NPC82111
0.8357	Intermediate Similarity	NPC227160
0.8333	Intermediate Similarity	NPC22130
0.8333	Intermediate Similarity	NPC100129
0.8333	Intermediate Similarity	NPC116838
0.8311	Intermediate Similarity	NPC189054
0.8301	Intermediate Similarity	NPC254163
0.8299	Intermediate Similarity	NPC473575
0.8298	Intermediate Similarity	NPC227002
0.8298	Intermediate Similarity	NPC100223
0.8298	Intermediate Similarity	NPC158526
0.8298	Intermediate Similarity	NPC33611
0.8298	Intermediate Similarity	NPC16830
0.8298	Intermediate Similarity	NPC129687
0.8298	Intermediate Similarity	NPC171928
0.8284	Intermediate Similarity	NPC344161
0.828	Intermediate Similarity	NPC116759
0.828	Intermediate Similarity	NPC14294
0.8273	Intermediate Similarity	NPC226862
0.8273	Intermediate Similarity	NPC165128
0.8273	Intermediate Similarity	NPC57119
0.8273	Intermediate Similarity	NPC158471
0.8267	Intermediate Similarity	NPC477698
0.8267	Intermediate Similarity	NPC474965
0.8267	Intermediate Similarity	NPC174512
0.8267	Intermediate Similarity	NPC668
0.8267	Intermediate Similarity	NPC477695
0.8267	Intermediate Similarity	NPC293757
0.8261	Intermediate Similarity	NPC213711
0.8261	Intermediate Similarity	NPC40352
0.8252	Intermediate Similarity	NPC89504
0.8252	Intermediate Similarity	NPC95485
0.8252	Intermediate Similarity	NPC88065
0.8252	Intermediate Similarity	NPC72796
0.8252	Intermediate Similarity	NPC44245
0.8243	Intermediate Similarity	NPC474158
0.8243	Intermediate Similarity	NPC229787
0.8235	Intermediate Similarity	NPC348849
0.8235	Intermediate Similarity	NPC178195
0.8228	Intermediate Similarity	NPC222531
0.8224	Intermediate Similarity	NPC56184
0.8224	Intermediate Similarity	NPC118332
0.8212	Intermediate Similarity	NPC229882
0.8212	Intermediate Similarity	NPC261322
0.8212	Intermediate Similarity	NPC158635
0.8207	Intermediate Similarity	NPC178290
0.8194	Intermediate Similarity	NPC11453
0.8194	Intermediate Similarity	NPC90431
0.8182	Intermediate Similarity	NPC47181
0.8176	Intermediate Similarity	NPC306475
0.8176	Intermediate Similarity	NPC471923
0.8176	Intermediate Similarity	NPC15743
0.817	Intermediate Similarity	NPC308555
0.8158	Intermediate Similarity	NPC477700
0.8153	Intermediate Similarity	NPC258322
0.8153	Intermediate Similarity	NPC191352
0.8148	Intermediate Similarity	NPC184624
0.8141	Intermediate Similarity	NPC68619
0.8138	Intermediate Similarity	NPC196420
0.8133	Intermediate Similarity	NPC153620
0.8133	Intermediate Similarity	NPC24257
0.8129	Intermediate Similarity	NPC478055
0.8125	Intermediate Similarity	NPC18576
0.8125	Intermediate Similarity	NPC473531
0.8125	Intermediate Similarity	NPC475453
0.8125	Intermediate Similarity	NPC185498
0.8125	Intermediate Similarity	NPC189474
0.8121	Intermediate Similarity	NPC223185
0.8121	Intermediate Similarity	NPC327052
0.8108	Intermediate Similarity	NPC472564
0.8105	Intermediate Similarity	NPC477699
0.8099	Intermediate Similarity	NPC192255
0.8095	Intermediate Similarity	NPC100675
0.8089	Intermediate Similarity	NPC218471
0.8089	Intermediate Similarity	NPC65784
0.8089	Intermediate Similarity	NPC239818
0.8082	Intermediate Similarity	NPC318575
0.8071	Intermediate Similarity	NPC64948
0.8069	Intermediate Similarity	NPC143895
0.8063	Intermediate Similarity	NPC174734
0.8063	Intermediate Similarity	NPC474042
0.8058	Intermediate Similarity	NPC85830
0.8056	Intermediate Similarity	NPC170779
0.8056	Intermediate Similarity	NPC90083
0.8056	Intermediate Similarity	NPC31530
0.8054	Intermediate Similarity	NPC18211
0.8054	Intermediate Similarity	NPC141569
0.8054	Intermediate Similarity	NPC477701
0.8054	Intermediate Similarity	NPC166884
0.8052	Intermediate Similarity	NPC299706
0.8052	Intermediate Similarity	NPC115466
0.8052	Intermediate Similarity	NPC178574
0.8052	Intermediate Similarity	NPC61604
0.8052	Intermediate Similarity	NPC65591
0.8052	Intermediate Similarity	NPC245615
0.8042	Intermediate Similarity	NPC7744
0.8041	Intermediate Similarity	NPC31751

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 NPC218092 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	881
0.2-0.3	1440
0.3-0.4	2604
0.4-0.5	2113
0.5-0.6	1162
0.6-0.7	551
0.7-0.8	79
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8609	High Similarity	NPD4966	Approved
0.8609	High Similarity	NPD4967	Phase 2
0.8609	High Similarity	NPD4965	Approved
0.8497	Intermediate Similarity	NPD6234	Discontinued
0.8411	Intermediate Similarity	NPD37	Approved
0.8243	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7228	Approved
0.8038	Intermediate Similarity	NPD7199	Phase 2
0.7937	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7240	Approved
0.7922	Intermediate Similarity	NPD7028	Phase 2
0.7917	Intermediate Similarity	NPD2979	Phase 3
0.7899	Intermediate Similarity	NPD1281	Approved
0.7899	Intermediate Similarity	NPD3705	Approved
0.7891	Intermediate Similarity	NPD2438	Suspended
0.7847	Intermediate Similarity	NPD8032	Phase 2
0.7843	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD4110	Phase 3
0.7784	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD5283	Phase 1
0.7748	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1283	Approved
0.7681	Intermediate Similarity	NPD1651	Approved
0.7651	Intermediate Similarity	NPD2531	Phase 2
0.7529	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6355	Discontinued
0.7436	Intermediate Similarity	NPD6273	Approved
0.7432	Intermediate Similarity	NPD4140	Approved
0.7432	Intermediate Similarity	NPD4060	Phase 1
0.7429	Intermediate Similarity	NPD5691	Approved
0.7415	Intermediate Similarity	NPD6798	Discontinued
0.741	Intermediate Similarity	NPD5536	Phase 2
0.7405	Intermediate Similarity	NPD7458	Discontinued
0.7389	Intermediate Similarity	NPD7680	Approved
0.7383	Intermediate Similarity	NPD3657	Discovery
0.7378	Intermediate Similarity	NPD8127	Discontinued
0.7365	Intermediate Similarity	NPD6663	Approved
0.7347	Intermediate Similarity	NPD7095	Approved
0.7338	Intermediate Similarity	NPD8166	Discontinued
0.7315	Intermediate Similarity	NPD3620	Phase 2
0.7315	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5585	Approved
0.7299	Intermediate Similarity	NPD5535	Approved
0.7292	Intermediate Similarity	NPD5327	Phase 3
0.7285	Intermediate Similarity	NPD7097	Phase 1
0.7273	Intermediate Similarity	NPD6674	Discontinued
0.7267	Intermediate Similarity	NPD1933	Approved
0.7263	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD17	Approved
0.7248	Intermediate Similarity	NPD6233	Phase 2
0.723	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6232	Discontinued
0.7222	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD5736	Approved
0.7202	Intermediate Similarity	NPD7473	Discontinued
0.7183	Intermediate Similarity	NPD3025	Approved
0.7183	Intermediate Similarity	NPD1357	Approved
0.7183	Intermediate Similarity	NPD3024	Approved
0.7181	Intermediate Similarity	NPD3764	Approved
0.7134	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4626	Approved
0.7124	Intermediate Similarity	NPD4108	Discontinued
0.7123	Intermediate Similarity	NPD1876	Approved
0.7118	Intermediate Similarity	NPD5844	Phase 1
0.7117	Intermediate Similarity	NPD8455	Phase 2
0.7115	Intermediate Similarity	NPD7003	Approved
0.7113	Intermediate Similarity	NPD1894	Discontinued
0.7108	Intermediate Similarity	NPD5494	Approved
0.7105	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1608	Approved
0.7102	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6873	Phase 2
0.7097	Intermediate Similarity	NPD5958	Discontinued
0.7083	Intermediate Similarity	NPD3026	Approved
0.7083	Intermediate Similarity	NPD3023	Approved
0.7081	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4477	Approved
0.7078	Intermediate Similarity	NPD4476	Approved
0.7067	Intermediate Similarity	NPD5111	Phase 2
0.7067	Intermediate Similarity	NPD5109	Approved
0.7067	Intermediate Similarity	NPD5110	Phase 2
0.7059	Intermediate Similarity	NPD3818	Discontinued
0.7055	Intermediate Similarity	NPD4359	Approved
0.7055	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5735	Approved
0.7034	Intermediate Similarity	NPD1611	Approved
0.7032	Intermediate Similarity	NPD5763	Approved
0.7032	Intermediate Similarity	NPD2346	Discontinued
0.7032	Intermediate Similarity	NPD5762	Approved
0.7024	Intermediate Similarity	NPD7229	Phase 3
0.702	Intermediate Similarity	NPD4062	Phase 3
0.7017	Intermediate Similarity	NPD4420	Approved
0.7014	Intermediate Similarity	NPD3019	Approved
0.7013	Intermediate Similarity	NPD2799	Discontinued
0.7011	Intermediate Similarity	NPD7280	Phase 3
0.7011	Intermediate Similarity	NPD7281	Phase 3
0.7006	Intermediate Similarity	NPD4628	Phase 3
0.6994	Remote Similarity	NPD6386	Approved
0.6994	Remote Similarity	NPD6385	Approved
0.6994	Remote Similarity	NPD7685	Pre-registration
0.6987	Remote Similarity	NPD2897	Discontinued
0.697	Remote Similarity	NPD5978	Approved
0.697	Remote Similarity	NPD5977	Approved
0.6966	Remote Similarity	NPD3847	Discontinued
0.6959	Remote Similarity	NPD3266	Approved
0.6959	Remote Similarity	NPD3267	Approved
0.6959	Remote Similarity	NPD2797	Approved
0.6957	Remote Similarity	NPD7427	Discontinued
0.6937	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1358	Approved
0.6933	Remote Similarity	NPD2614	Approved
0.6928	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4618	Approved
0.6928	Remote Similarity	NPD4622	Approved
0.6927	Remote Similarity	NPD7296	Approved
0.6914	Remote Similarity	NPD8313	Approved
0.6914	Remote Similarity	NPD8312	Approved
0.6913	Remote Similarity	NPD2798	Approved
0.6913	Remote Similarity	NPD4624	Approved
0.6903	Remote Similarity	NPD3748	Approved
0.6897	Remote Similarity	NPD2932	Approved
0.689	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7110	Phase 1
0.6883	Remote Similarity	NPD6353	Approved
0.6879	Remote Similarity	NPD4534	Discontinued
0.6871	Remote Similarity	NPD3972	Approved
0.6867	Remote Similarity	NPD3817	Phase 2
0.6865	Remote Similarity	NPD5006	Approved
0.6865	Remote Similarity	NPD5005	Approved
0.6861	Remote Similarity	NPD3134	Approved
0.6859	Remote Similarity	NPD2935	Discontinued
0.6855	Remote Similarity	NPD6190	Approved
0.6852	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4727	Phase 1
0.6842	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3268	Approved
0.6842	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4481	Phase 3
0.6839	Remote Similarity	NPD5688	Approved
0.6839	Remote Similarity	NPD5689	Approved
0.6835	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3146	Approved
0.6829	Remote Similarity	NPD6876	Approved
0.6829	Remote Similarity	NPD6875	Approved
0.6824	Remote Similarity	NPD3787	Discontinued
0.6824	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7266	Discontinued
0.6815	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7819	Suspended
0.6806	Remote Similarity	NPD7827	Phase 1
0.6803	Remote Similarity	NPD1535	Discovery
0.68	Remote Similarity	NPD5647	Approved
0.6797	Remote Similarity	NPD4870	Approved
0.6795	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6331	Phase 2
0.679	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5242	Approved
0.6776	Remote Similarity	NPD3027	Phase 3
0.6774	Remote Similarity	NPD2653	Approved
0.6774	Remote Similarity	NPD2492	Phase 1
0.6774	Remote Similarity	NPD6653	Approved
0.6772	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7037	Approved
0.6768	Remote Similarity	NPD3226	Approved
0.6761	Remote Similarity	NPD1241	Discontinued
0.6761	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1481	Phase 2
0.6755	Remote Similarity	NPD9494	Approved
0.6752	Remote Similarity	NPD6032	Approved
0.6748	Remote Similarity	NPD3641	Approved
0.6748	Remote Similarity	NPD3639	Approved
0.6748	Remote Similarity	NPD3640	Phase 3
0.6747	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD919	Approved
0.6738	Remote Similarity	NPD228	Approved
0.6732	Remote Similarity	NPD2313	Discontinued
0.6732	Remote Similarity	NPD7985	Registered
0.6731	Remote Similarity	NPD7119	Phase 2
0.6728	Remote Similarity	NPD2533	Approved
0.6728	Remote Similarity	NPD2534	Approved
0.6728	Remote Similarity	NPD2532	Approved
0.6726	Remote Similarity	NPD3882	Suspended
0.6725	Remote Similarity	NPD7315	Approved
0.6723	Remote Similarity	NPD2968	Approved
0.6723	Remote Similarity	NPD2971	Approved
0.6722	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD5451	Approved
0.6711	Remote Similarity	NPD6832	Phase 2
0.6711	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.671	Remote Similarity	NPD447	Suspended
0.6709	Remote Similarity	NPD6002	Phase 3
0.6709	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD1471	Phase 3
0.6709	Remote Similarity	NPD6004	Phase 3
0.6709	Remote Similarity	NPD6005	Phase 3

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