NPASS Compound

Structure

CID217394 OpenBabel06191716012D 23 25 0 0 1 0 0 0 0 0999 V2000 -2.8147 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2788 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 -2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -1.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4128 -1.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 0.4612 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 13 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 1 0 0 0 16 19 1 0 0 0 0 16 20 1 1 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	347.268
LogP:	4.274
LogD:	3.748
LogS:	-4.413
# Rotatable Bonds:	2
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.612
Synthetic Accessibility Score:	4.849
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.497
MDCK Permeability:	2.4418026441708207e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.058
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.8
Plasma Protein Binding (PPB):	67.75261688232422%
Volume Distribution (VD):	1.432
Pgp-substrate:	39.457435607910156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.377
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.666
CYP2C9-inhibitor:	0.191
CYP2C9-substrate:	0.137
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.453
CYP3A4-inhibitor:	0.641
CYP3A4-substrate:	0.284

ADMET: Excretion

Clearance (CL):	15.946
Half-life (T1/2):	0.037

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.049
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.725
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.146
Carcinogencity:	0.369
Eye Corrosion:	0.038
Eye Irritation:	0.05
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC217394

Natural Product ID:	NPC217394
*Common Name:**	Coronarin D
IUPAC Name:	(3Z)-3-[2-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-hydroxyoxolan-2-one
Synonyms:	Coronarin D
Standard InCHIKey:	DYYYQLXAGIXUGM-FKKKBMQXSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-13-6-9-16-19(2,3)10-5-11-20(16,4)15(13)8-7-14-12-17(21)23-18(14)22/h7,15-17,21H,1,5-6,8-12H2,2-4H3/b14-7-/t15-,16-,17?,20+/m0/s1
SMILES:	OC1OC(=O)/C(=CC[C@H]2C(=C)CC[C@@H]3[C@]2(C)CCCC3(C)C)/C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1288153
PubChem CID:	52947373
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21106458]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23738470]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[23738470]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23755850]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[25275213]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868158]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	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	4
IC50	1
Others	4

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	GI50	=	8000.0	nM	PMID[549615]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	14000.0	nM	PMID[549615]
NPT136	Cell Line	SK-N-SH	Homo sapiens	GI50	=	20100.0	nM	PMID[549615]
NPT136	Cell Line	SK-N-SH	Homo sapiens	LC50	=	32000.0	nM	PMID[549615]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	17400.0	nM	PMID[549615]
NPT83	Cell Line	MCF7	Homo sapiens	LC50	=	21900.0	nM	PMID[549615]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	47000.0	nM	PMID[549615]
NPT165	Cell Line	HeLa	Homo sapiens	LC50	=	60600.0	nM	PMID[549615]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	41720.0	nM	PMID[549616]

☑ 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 NPC217394 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	154
0.1-0.2	997
0.2-0.3	5633
0.3-0.4	14645
0.4-0.5	8477
0.5-0.6	7487
0.6-0.7	4770
0.7-0.8	503
0.8-0.85	22
0.85-0.9	4
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC469
0.875	High Similarity	NPC166346
0.8681	High Similarity	NPC473154
0.8495	Intermediate Similarity	NPC63249
0.8427	Intermediate Similarity	NPC477783
0.8409	Intermediate Similarity	NPC474396
0.8409	Intermediate Similarity	NPC79027
0.8409	Intermediate Similarity	NPC50488
0.8409	Intermediate Similarity	NPC251528
0.8404	Intermediate Similarity	NPC134077
0.8372	Intermediate Similarity	NPC329630
0.8315	Intermediate Similarity	NPC253186
0.8315	Intermediate Similarity	NPC477782
0.8295	Intermediate Similarity	NPC474629
0.8256	Intermediate Similarity	NPC470800
0.8222	Intermediate Similarity	NPC72845
0.8222	Intermediate Similarity	NPC65513
0.8161	Intermediate Similarity	NPC42586
0.8161	Intermediate Similarity	NPC30984
0.8161	Intermediate Similarity	NPC86316
0.8161	Intermediate Similarity	NPC473251
0.8161	Intermediate Similarity	NPC106416
0.809	Intermediate Similarity	NPC472809
0.809	Intermediate Similarity	NPC472810
0.8068	Intermediate Similarity	NPC329692
0.8043	Intermediate Similarity	NPC57117
0.8022	Intermediate Similarity	NPC472811
0.8	Intermediate Similarity	NPC168131
0.7979	Intermediate Similarity	NPC204054
0.7979	Intermediate Similarity	NPC257726
0.7979	Intermediate Similarity	NPC475709
0.7955	Intermediate Similarity	NPC65661
0.7952	Intermediate Similarity	NPC4509
0.7935	Intermediate Similarity	NPC469939
0.7935	Intermediate Similarity	NPC472812
0.7935	Intermediate Similarity	NPC242069
0.7931	Intermediate Similarity	NPC42476
0.7927	Intermediate Similarity	NPC75485
0.7927	Intermediate Similarity	NPC168975
0.7895	Intermediate Similarity	NPC474440
0.7882	Intermediate Similarity	NPC17550
0.7857	Intermediate Similarity	NPC473756
0.7849	Intermediate Similarity	NPC470255
0.7849	Intermediate Similarity	NPC469697
0.7826	Intermediate Similarity	NPC179517
0.7826	Intermediate Similarity	NPC165904
0.7812	Intermediate Similarity	NPC477720
0.7802	Intermediate Similarity	NPC470734
0.7802	Intermediate Similarity	NPC174342
0.7789	Intermediate Similarity	NPC73911
0.7789	Intermediate Similarity	NPC474343
0.7789	Intermediate Similarity	NPC76266
0.7727	Intermediate Similarity	NPC311070
0.7727	Intermediate Similarity	NPC22611
0.7717	Intermediate Similarity	NPC182136
0.7717	Intermediate Similarity	NPC51486
0.7717	Intermediate Similarity	NPC310479
0.7711	Intermediate Similarity	NPC238146
0.7708	Intermediate Similarity	NPC124512
0.7708	Intermediate Similarity	NPC278386
0.7708	Intermediate Similarity	NPC159763
0.7684	Intermediate Similarity	NPC162346
0.767	Intermediate Similarity	NPC194951
0.767	Intermediate Similarity	NPC12046
0.7667	Intermediate Similarity	NPC474062
0.7667	Intermediate Similarity	NPC211892
0.7667	Intermediate Similarity	NPC173917
0.7667	Intermediate Similarity	NPC118266
0.766	Intermediate Similarity	NPC298973
0.766	Intermediate Similarity	NPC104925
0.766	Intermediate Similarity	NPC324078
0.764	Intermediate Similarity	NPC471302
0.764	Intermediate Similarity	NPC126518
0.7634	Intermediate Similarity	NPC233345
0.7634	Intermediate Similarity	NPC477122
0.7634	Intermediate Similarity	NPC472814
0.7634	Intermediate Similarity	NPC186363
0.7634	Intermediate Similarity	NPC177037
0.7614	Intermediate Similarity	NPC323251
0.7614	Intermediate Similarity	NPC16321
0.7614	Intermediate Similarity	NPC324170
0.7614	Intermediate Similarity	NPC200513
0.7614	Intermediate Similarity	NPC94200
0.7609	Intermediate Similarity	NPC5509
0.76	Intermediate Similarity	NPC218158
0.7596	Intermediate Similarity	NPC157441
0.7596	Intermediate Similarity	NPC264153
0.759	Intermediate Similarity	NPC144947
0.7579	Intermediate Similarity	NPC183012
0.7579	Intermediate Similarity	NPC209355
0.7579	Intermediate Similarity	NPC472441
0.7556	Intermediate Similarity	NPC471795
0.7556	Intermediate Similarity	NPC329738
0.7556	Intermediate Similarity	NPC474860
0.7556	Intermediate Similarity	NPC471300
0.7556	Intermediate Similarity	NPC163606
0.7553	Intermediate Similarity	NPC205034
0.7553	Intermediate Similarity	NPC156553
0.7553	Intermediate Similarity	NPC162615
0.7553	Intermediate Similarity	NPC139692
0.7553	Intermediate Similarity	NPC470656
0.7553	Intermediate Similarity	NPC152778
0.7528	Intermediate Similarity	NPC472440
0.7527	Intermediate Similarity	NPC281942
0.7527	Intermediate Similarity	NPC232426
0.7527	Intermediate Similarity	NPC221111
0.7527	Intermediate Similarity	NPC280149
0.75	Intermediate Similarity	NPC229584
0.75	Intermediate Similarity	NPC470801
0.75	Intermediate Similarity	NPC20025
0.75	Intermediate Similarity	NPC196407
0.75	Intermediate Similarity	NPC73858
0.75	Intermediate Similarity	NPC40228
0.75	Intermediate Similarity	NPC185587
0.75	Intermediate Similarity	NPC14203
0.75	Intermediate Similarity	NPC112654
0.7476	Intermediate Similarity	NPC235014
0.7475	Intermediate Similarity	NPC238397
0.7475	Intermediate Similarity	NPC471363
0.7474	Intermediate Similarity	NPC476415
0.7473	Intermediate Similarity	NPC131813
0.7473	Intermediate Similarity	NPC85698
0.7451	Intermediate Similarity	NPC392
0.7451	Intermediate Similarity	NPC177524
0.7451	Intermediate Similarity	NPC219900
0.7449	Intermediate Similarity	NPC161527
0.7449	Intermediate Similarity	NPC477972
0.7449	Intermediate Similarity	NPC47024
0.7449	Intermediate Similarity	NPC20113
0.7449	Intermediate Similarity	NPC219285
0.7449	Intermediate Similarity	NPC477968
0.7449	Intermediate Similarity	NPC324841
0.7449	Intermediate Similarity	NPC477971
0.7449	Intermediate Similarity	NPC228251
0.7447	Intermediate Similarity	NPC141831
0.7426	Intermediate Similarity	NPC172867
0.7423	Intermediate Similarity	NPC477719
0.7423	Intermediate Similarity	NPC477718
0.7423	Intermediate Similarity	NPC98112
0.7419	Intermediate Similarity	NPC293044
0.7419	Intermediate Similarity	NPC471654
0.7416	Intermediate Similarity	NPC471296
0.7416	Intermediate Similarity	NPC186276
0.7416	Intermediate Similarity	NPC471298
0.74	Intermediate Similarity	NPC127933
0.74	Intermediate Similarity	NPC120009
0.74	Intermediate Similarity	NPC134270
0.74	Intermediate Similarity	NPC475889
0.74	Intermediate Similarity	NPC7613
0.74	Intermediate Similarity	NPC7644
0.7396	Intermediate Similarity	NPC13924
0.7391	Intermediate Similarity	NPC305029
0.7391	Intermediate Similarity	NPC475678
0.7391	Intermediate Similarity	NPC312561
0.7386	Intermediate Similarity	NPC195424
0.7386	Intermediate Similarity	NPC10636
0.7381	Intermediate Similarity	NPC476489
0.7381	Intermediate Similarity	NPC476490
0.7368	Intermediate Similarity	NPC53555
0.7368	Intermediate Similarity	NPC472303
0.7368	Intermediate Similarity	NPC277721
0.7368	Intermediate Similarity	NPC115021
0.7368	Intermediate Similarity	NPC267266
0.7363	Intermediate Similarity	NPC119001
0.7363	Intermediate Similarity	NPC472442
0.7363	Intermediate Similarity	NPC476602
0.7353	Intermediate Similarity	NPC109376
0.7353	Intermediate Similarity	NPC110496
0.7347	Intermediate Similarity	NPC23364
0.7347	Intermediate Similarity	NPC316598
0.734	Intermediate Similarity	NPC38952
0.734	Intermediate Similarity	NPC469403
0.734	Intermediate Similarity	NPC78973
0.734	Intermediate Similarity	NPC158488
0.7333	Intermediate Similarity	NPC118423
0.7333	Intermediate Similarity	NPC471297
0.7327	Intermediate Similarity	NPC470321
0.7327	Intermediate Similarity	NPC201880
0.7327	Intermediate Similarity	NPC264867
0.7327	Intermediate Similarity	NPC473207
0.7327	Intermediate Similarity	NPC81567
0.732	Intermediate Similarity	NPC16967
0.732	Intermediate Similarity	NPC319692
0.732	Intermediate Similarity	NPC165632
0.732	Intermediate Similarity	NPC473153
0.732	Intermediate Similarity	NPC325960
0.732	Intermediate Similarity	NPC234993
0.732	Intermediate Similarity	NPC242848
0.732	Intermediate Similarity	NPC134072
0.7312	Intermediate Similarity	NPC277771
0.7312	Intermediate Similarity	NPC226863
0.7312	Intermediate Similarity	NPC472378
0.73	Intermediate Similarity	NPC476081
0.73	Intermediate Similarity	NPC31058
0.73	Intermediate Similarity	NPC472815
0.73	Intermediate Similarity	NPC469606
0.73	Intermediate Similarity	NPC273005
0.7292	Intermediate Similarity	NPC474554
0.7292	Intermediate Similarity	NPC475572
0.7292	Intermediate Similarity	NPC88507

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 NPC217394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	1228
0.2-0.3	4390
0.3-0.4	2447
0.4-0.5	528
0.5-0.6	254
0.6-0.7	160
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7708	Intermediate Similarity	NPD4225	Approved
0.764	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6686	Approved
0.7	Intermediate Similarity	NPD7638	Approved
0.6931	Remote Similarity	NPD7640	Approved
0.6931	Remote Similarity	NPD7639	Approved
0.6809	Remote Similarity	NPD1694	Approved
0.6735	Remote Similarity	NPD7637	Suspended
0.67	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6399	Phase 3
0.6633	Remote Similarity	NPD5785	Approved
0.646	Remote Similarity	NPD7115	Discovery
0.6458	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6083	Phase 2
0.6408	Remote Similarity	NPD7902	Approved
0.6408	Remote Similarity	NPD6084	Phase 2
0.6404	Remote Similarity	NPD7327	Approved
0.6404	Remote Similarity	NPD7328	Approved
0.6392	Remote Similarity	NPD7521	Approved
0.6392	Remote Similarity	NPD6409	Approved
0.6392	Remote Similarity	NPD7334	Approved
0.6392	Remote Similarity	NPD7146	Approved
0.6392	Remote Similarity	NPD6684	Approved
0.6392	Remote Similarity	NPD5330	Approved
0.6392	Remote Similarity	NPD3618	Phase 1
0.6389	Remote Similarity	NPD6412	Phase 2
0.6379	Remote Similarity	NPD8033	Approved
0.6379	Remote Similarity	NPD7503	Approved
0.6354	Remote Similarity	NPD3666	Approved
0.6354	Remote Similarity	NPD3133	Approved
0.6354	Remote Similarity	NPD3665	Phase 1
0.6348	Remote Similarity	NPD7516	Approved
0.6346	Remote Similarity	NPD5696	Approved
0.6321	Remote Similarity	NPD7632	Discontinued
0.6316	Remote Similarity	NPD5209	Approved
0.6316	Remote Similarity	NPD3667	Approved
0.6303	Remote Similarity	NPD7507	Approved
0.63	Remote Similarity	NPD6698	Approved
0.63	Remote Similarity	NPD46	Approved
0.6293	Remote Similarity	NPD8377	Approved
0.6293	Remote Similarity	NPD8294	Approved
0.6277	Remote Similarity	NPD4695	Discontinued
0.6275	Remote Similarity	NPD7748	Approved
0.6264	Remote Similarity	NPD8039	Approved
0.6263	Remote Similarity	NPD6672	Approved
0.6263	Remote Similarity	NPD6903	Approved
0.6263	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD6882	Approved
0.6239	Remote Similarity	NPD8380	Approved
0.6239	Remote Similarity	NPD8378	Approved
0.6239	Remote Similarity	NPD8296	Approved
0.6239	Remote Similarity	NPD8379	Approved
0.6239	Remote Similarity	NPD8335	Approved
0.6239	Remote Similarity	NPD5697	Approved
0.6238	Remote Similarity	NPD5693	Phase 1
0.6238	Remote Similarity	NPD7515	Phase 2
0.6214	Remote Similarity	NPD5695	Phase 3
0.62	Remote Similarity	NPD6051	Approved
0.619	Remote Similarity	NPD4193	Approved
0.619	Remote Similarity	NPD4194	Approved
0.619	Remote Similarity	NPD4192	Approved
0.619	Remote Similarity	NPD4191	Approved
0.6186	Remote Similarity	NPD4786	Approved
0.6182	Remote Similarity	NPD6011	Approved
0.6182	Remote Similarity	NPD6899	Approved
0.6182	Remote Similarity	NPD6881	Approved
0.618	Remote Similarity	NPD4691	Approved
0.6163	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6650	Approved
0.6161	Remote Similarity	NPD6649	Approved
0.6148	Remote Similarity	NPD7319	Approved
0.6147	Remote Similarity	NPD6402	Approved
0.6147	Remote Similarity	NPD5739	Approved
0.6147	Remote Similarity	NPD7128	Approved
0.6147	Remote Similarity	NPD6675	Approved
0.6139	Remote Similarity	NPD7838	Discovery
0.6126	Remote Similarity	NPD6373	Approved
0.6126	Remote Similarity	NPD6014	Approved
0.6126	Remote Similarity	NPD6372	Approved
0.6126	Remote Similarity	NPD6012	Approved
0.6126	Remote Similarity	NPD6013	Approved
0.6126	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5363	Approved
0.6117	Remote Similarity	NPD7900	Approved
0.6117	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD5701	Approved
0.6078	Remote Similarity	NPD5284	Approved
0.6078	Remote Similarity	NPD5281	Approved
0.6078	Remote Similarity	NPD6079	Approved
0.6075	Remote Similarity	NPD5344	Discontinued
0.6071	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7102	Approved
0.6071	Remote Similarity	NPD6371	Approved
0.6071	Remote Similarity	NPD7290	Approved
0.6071	Remote Similarity	NPD6883	Approved
0.6067	Remote Similarity	NPD4137	Phase 3
0.6067	Remote Similarity	NPD6922	Approved
0.6067	Remote Similarity	NPD6923	Approved
0.6064	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4519	Discontinued
0.6061	Remote Similarity	NPD4623	Approved
0.6061	Remote Similarity	NPD5279	Phase 3
0.6058	Remote Similarity	NPD5210	Approved
0.6058	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4629	Approved
0.604	Remote Similarity	NPD4753	Phase 2
0.604	Remote Similarity	NPD5328	Approved
0.6036	Remote Similarity	NPD7320	Approved
0.6022	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4202	Approved
0.6018	Remote Similarity	NPD6869	Approved
0.6018	Remote Similarity	NPD8130	Phase 1
0.6018	Remote Similarity	NPD6617	Approved
0.6018	Remote Similarity	NPD6847	Approved
0.6	Remote Similarity	NPD7144	Approved
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD4747	Approved
0.6	Remote Similarity	NPD7143	Approved
0.598	Remote Similarity	NPD5207	Approved
0.5979	Remote Similarity	NPD4223	Phase 3
0.5979	Remote Similarity	NPD4221	Approved
0.5978	Remote Similarity	NPD6926	Approved
0.5978	Remote Similarity	NPD4058	Approved
0.5978	Remote Similarity	NPD6924	Approved
0.5965	Remote Similarity	NPD6053	Discontinued
0.5965	Remote Similarity	NPD8297	Approved
0.5962	Remote Similarity	NPD6001	Approved
0.596	Remote Similarity	NPD1696	Phase 3
0.5957	Remote Similarity	NPD5776	Phase 2
0.5957	Remote Similarity	NPD6925	Approved
0.5946	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5208	Approved
0.5938	Remote Similarity	NPD4819	Approved
0.5938	Remote Similarity	NPD7514	Phase 3
0.5938	Remote Similarity	NPD7332	Phase 2
0.5938	Remote Similarity	NPD4821	Approved
0.5938	Remote Similarity	NPD4820	Approved
0.5938	Remote Similarity	NPD4822	Approved
0.5935	Remote Similarity	NPD7736	Approved
0.5934	Remote Similarity	NPD7152	Approved
0.5934	Remote Similarity	NPD7151	Approved
0.5934	Remote Similarity	NPD7150	Approved
0.5922	Remote Similarity	NPD8035	Phase 2
0.5922	Remote Similarity	NPD8034	Phase 2
0.5922	Remote Similarity	NPD6411	Approved
0.5918	Remote Similarity	NPD5362	Discontinued
0.5918	Remote Similarity	NPD6695	Phase 3
0.5918	Remote Similarity	NPD7154	Phase 3
0.5917	Remote Similarity	NPD6370	Approved
0.5914	Remote Similarity	NPD8264	Approved
0.5914	Remote Similarity	NPD7339	Approved
0.5914	Remote Similarity	NPD6942	Approved
0.5913	Remote Similarity	NPD8133	Approved
0.59	Remote Similarity	NPD4249	Approved
0.59	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6009	Approved
0.5895	Remote Similarity	NPD4271	Approved
0.5895	Remote Similarity	NPD7145	Approved
0.5895	Remote Similarity	NPD4268	Approved
0.5882	Remote Similarity	NPD6673	Approved
0.5882	Remote Similarity	NPD1695	Approved
0.5882	Remote Similarity	NPD6904	Approved
0.5882	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6080	Approved
0.5877	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6902	Approved
0.5872	Remote Similarity	NPD5211	Phase 2
0.5868	Remote Similarity	NPD8328	Phase 3
0.5865	Remote Similarity	NPD5779	Approved
0.5865	Remote Similarity	NPD5778	Approved
0.5859	Remote Similarity	NPD4197	Approved
0.5854	Remote Similarity	NPD8293	Discontinued
0.5851	Remote Similarity	NPD6933	Approved
0.5849	Remote Similarity	NPD5222	Approved
0.5849	Remote Similarity	NPD4697	Phase 3
0.5849	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD5221	Approved
0.5842	Remote Similarity	NPD4250	Approved
0.5842	Remote Similarity	NPD4251	Approved
0.5841	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8513	Phase 3
0.5833	Remote Similarity	NPD6404	Discontinued
0.5833	Remote Similarity	NPD8516	Approved
0.5833	Remote Similarity	NPD6929	Approved
0.5833	Remote Similarity	NPD8515	Approved
0.5833	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8517	Approved
0.5833	Remote Similarity	NPD6648	Approved
0.5833	Remote Similarity	NPD5285	Approved
0.5833	Remote Similarity	NPD5286	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