NPASS Compound

Structure

CID123360 OpenBabel06191715482D 24 26 0 0 1 0 0 0 0 0999 V2000 -1.9469 -2.9851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9472 -0.7364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1890 -1.6938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6490 -2.2481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2978 -1.8735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.8737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5963 -1.8733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5963 -1.1238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2983 0.3749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5960 0.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6487 -0.7493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9469 -2.2483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9472 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9576 -0.9809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -1.1239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6489 -0.0001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2451 -0.7492 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2453 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3981 -0.3749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3245 -0.5619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1475 -0.3751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 -0.5618 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 -3.9579 0.2313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 12 2 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 9 13 1 0 0 0 0 10 13 2 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 9 1 1 0 0 0 16 23 1 0 0 0 0 17 8 1 6 0 0 0 17 18 1 0 0 0 0 18 10 1 1 0 0 0 18 24 1 0 0 0 0 19 21 2 0 0 0 0 19 24 1 0 0 0 0 20 22 2 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.17
Volume:	348.149
LogP:	4.155
LogD:	3.675
LogS:	-4.711
# Rotatable Bonds:	0
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.439
Synthetic Accessibility Score:	5.53
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.832
MDCK Permeability:	2.0659224901464768e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.796
20% Bioavailability (F20%):	0.576
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	93.28375244140625%
Volume Distribution (VD):	0.284
Pgp-substrate:	1.0444989204406738%

ADMET: Metabolism

CYP1A2-inhibitor:	0.286
CYP1A2-substrate:	0.522
CYP2C19-inhibitor:	0.711
CYP2C19-substrate:	0.098
CYP2C9-inhibitor:	0.773
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.188
CYP2D6-substrate:	0.769
CYP3A4-inhibitor:	0.292
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	3.488
Half-life (T1/2):	0.571

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.696
Drug-inuced Liver Injury (DILI):	0.482
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.816
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.595
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.898

Download Data

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

Natural Product: NPC123360

Natural Product ID:	NPC123360
*Common Name:**	Ovatodiolide
IUPAC Name:	n.a.
Synonyms:	Ovatodiolide
Standard InCHIKey:	KTYZKXFERQUCPX-XGKXUXTPSA-N
Standard InCHI:	InChI=1S/C20H24O4/c1-12-5-4-6-15-11-16(23-20(15)22)9-13(2)10-18-17(8-7-12)14(3)19(21)24-18/h5,10-11,16-18H,3-4,6-9H2,1-2H3/b12-5+,13-10+/t16-,17-,18+/m1/s1
SMILES:	C/C/1=CCCC2=C[C@H](OC2=O)C/C(=C/[C@H]2[C@H](CC1)C(=C)C(=O)O2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470287
PubChem CID:	6451060
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene 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
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	heartwood	n.a.	n.a.	PMID[16643064]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18547115]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19099464]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19697926]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2421673]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	aerial parts	Muli County, Sichuan Province, China	2011-AUG	PMID[24219809]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	roots	Khon Kaen, Thailand	2009-DEC	PMID[25537111]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26178912]
NPO33150	Artocarpus communis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26178912]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9599286]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16409	Quercus pedunculata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1558	Ozothamnus obcordatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16021	Boletus bovinus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20543	Psydrax livida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17240	Crematogaster brevis	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20115	Melampodium argophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21614	Urceolaria scruposa	Species	Trichodinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19889	Cereus stellatus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17508	Danae racemosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19763	Meloidogyne incognita	Species	Meloidogynidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19768	Xylosalsola arbuscula	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20336	Arctotheca calendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28799	Hyptis suaveolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20470	Elaeagnus orientalis	Species	Elaeagnaceae	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
IC50	14

Activity Type	# Activity
Cell Line	8
CELL-LINE	2
NON-MOLECULAR	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	10000.0	nM	PMID[448178]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	9600.0	nM	PMID[448178]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	9500.0	nM	PMID[448178]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	9500.0	nM	PMID[448178]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	1250.0	nM	PMID[448179]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	1960.0	nM	PMID[448179]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	1400.0	nM	PMID[448179]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	32600.0	nM	PMID[448180]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7400.0	nM	PMID[448178]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	>	100000.0	nM	PMID[448178]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	19700.0	nM	PMID[448178]
NPT610	Others	Molecular identity unknown		IC50	=	4000.0	nM	PMID[448180]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12100.0	nM	PMID[448180]
NPT27	Others	Unspecified		IC50	>	30500.0	nM	PMID[448180]

☑ 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 NPC123360 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	180
0.1-0.2	1300
0.2-0.3	6321
0.3-0.4	15850
0.4-0.5	9513
0.5-0.6	6100
0.6-0.7	2494
0.7-0.8	753
0.8-0.85	124
0.85-0.9	46
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC476355
0.9437	High Similarity	NPC140287
0.9429	High Similarity	NPC163003
0.9211	High Similarity	NPC173609
0.9189	High Similarity	NPC93763
0.9189	High Similarity	NPC108816
0.9067	High Similarity	NPC178277
0.9067	High Similarity	NPC270126
0.9054	High Similarity	NPC171204
0.9054	High Similarity	NPC57744
0.9054	High Similarity	NPC476028
0.9054	High Similarity	NPC97516
0.9054	High Similarity	NPC141789
0.9028	High Similarity	NPC58956
0.9028	High Similarity	NPC295633
0.9028	High Similarity	NPC269206
0.8947	High Similarity	NPC281132
0.8933	High Similarity	NPC128276
0.8861	High Similarity	NPC215364
0.8857	High Similarity	NPC194871
0.8846	High Similarity	NPC475947
0.8831	High Similarity	NPC471325
0.88	High Similarity	NPC320630
0.88	High Similarity	NPC116177
0.88	High Similarity	NPC187568
0.88	High Similarity	NPC7563
0.88	High Similarity	NPC470240
0.88	High Similarity	NPC476794
0.88	High Similarity	NPC41780
0.875	High Similarity	NPC284902
0.8732	High Similarity	NPC470256
0.8684	High Similarity	NPC267231
0.8667	High Similarity	NPC235906
0.8649	High Similarity	NPC259599
0.8649	High Similarity	NPC15499
0.8649	High Similarity	NPC117746
0.8649	High Similarity	NPC294434
0.8642	High Similarity	NPC160138
0.8642	High Similarity	NPC475703
0.863	High Similarity	NPC84038
0.8608	High Similarity	NPC169575
0.8608	High Similarity	NPC40746
0.859	High Similarity	NPC42470
0.859	High Similarity	NPC25684
0.859	High Similarity	NPC141810
0.859	High Similarity	NPC281949
0.859	High Similarity	NPC301477
0.8553	High Similarity	NPC65603
0.8533	High Similarity	NPC155587
0.8533	High Similarity	NPC226669
0.8533	High Similarity	NPC138408
0.8533	High Similarity	NPC193351
0.8519	High Similarity	NPC107787
0.8514	High Similarity	NPC474705
0.85	High Similarity	NPC115786
0.8493	Intermediate Similarity	NPC67183
0.8472	Intermediate Similarity	NPC218477
0.8462	Intermediate Similarity	NPC302426
0.8462	Intermediate Similarity	NPC223904
0.8451	Intermediate Similarity	NPC248125
0.8442	Intermediate Similarity	NPC196653
0.8442	Intermediate Similarity	NPC471465
0.8442	Intermediate Similarity	NPC299235
0.8434	Intermediate Similarity	NPC295312
0.84	Intermediate Similarity	NPC474758
0.8395	Intermediate Similarity	NPC78089
0.8395	Intermediate Similarity	NPC470755
0.8378	Intermediate Similarity	NPC129665
0.8375	Intermediate Similarity	NPC473390
0.8375	Intermediate Similarity	NPC318468
0.8375	Intermediate Similarity	NPC131669
0.8375	Intermediate Similarity	NPC59097
0.8356	Intermediate Similarity	NPC88877
0.8356	Intermediate Similarity	NPC476591
0.8354	Intermediate Similarity	NPC325031
0.8354	Intermediate Similarity	NPC24417
0.8333	Intermediate Similarity	NPC167881
0.8333	Intermediate Similarity	NPC617
0.8333	Intermediate Similarity	NPC98557
0.8333	Intermediate Similarity	NPC264227
0.8333	Intermediate Similarity	NPC63649
0.8333	Intermediate Similarity	NPC472965
0.8333	Intermediate Similarity	NPC182550
0.8313	Intermediate Similarity	NPC226863
0.8312	Intermediate Similarity	NPC10572
0.8293	Intermediate Similarity	NPC305475
0.8293	Intermediate Similarity	NPC475461
0.8272	Intermediate Similarity	NPC476804
0.8272	Intermediate Similarity	NPC158756
0.825	Intermediate Similarity	NPC229825
0.825	Intermediate Similarity	NPC35556
0.8228	Intermediate Similarity	NPC74673
0.8228	Intermediate Similarity	NPC69271
0.8228	Intermediate Similarity	NPC276356
0.8205	Intermediate Similarity	NPC472960
0.8171	Intermediate Similarity	NPC21469
0.8171	Intermediate Similarity	NPC255307
0.8148	Intermediate Similarity	NPC39588
0.8148	Intermediate Similarity	NPC250315
0.814	Intermediate Similarity	NPC475657
0.8133	Intermediate Similarity	NPC186531
0.8125	Intermediate Similarity	NPC35089
0.8125	Intermediate Similarity	NPC10276
0.8118	Intermediate Similarity	NPC80875
0.8101	Intermediate Similarity	NPC470239
0.8101	Intermediate Similarity	NPC470244
0.8095	Intermediate Similarity	NPC475819
0.8095	Intermediate Similarity	NPC469631
0.8095	Intermediate Similarity	NPC469653
0.8095	Intermediate Similarity	NPC471047
0.8095	Intermediate Similarity	NPC469628
0.8095	Intermediate Similarity	NPC475906
0.8095	Intermediate Similarity	NPC476805
0.8082	Intermediate Similarity	NPC472266
0.8077	Intermediate Similarity	NPC474760
0.8072	Intermediate Similarity	NPC469483
0.8072	Intermediate Similarity	NPC261721
0.8072	Intermediate Similarity	NPC64153
0.8072	Intermediate Similarity	NPC150755
0.8072	Intermediate Similarity	NPC279859
0.8072	Intermediate Similarity	NPC469910
0.8072	Intermediate Similarity	NPC50637
0.8072	Intermediate Similarity	NPC38576
0.8052	Intermediate Similarity	NPC244166
0.8052	Intermediate Similarity	NPC329852
0.8049	Intermediate Similarity	NPC96259
0.8049	Intermediate Similarity	NPC141193
0.8049	Intermediate Similarity	NPC159635
0.8049	Intermediate Similarity	NPC191476
0.8049	Intermediate Similarity	NPC114979
0.8046	Intermediate Similarity	NPC473330
0.8046	Intermediate Similarity	NPC140543
0.8046	Intermediate Similarity	NPC473316
0.8028	Intermediate Similarity	NPC474658
0.8025	Intermediate Similarity	NPC475690
0.8	Intermediate Similarity	NPC472955
0.8	Intermediate Similarity	NPC268298
0.8	Intermediate Similarity	NPC166919
0.8	Intermediate Similarity	NPC469660
0.7976	Intermediate Similarity	NPC266957
0.7976	Intermediate Similarity	NPC72513
0.7976	Intermediate Similarity	NPC231889
0.7975	Intermediate Similarity	NPC471220
0.7952	Intermediate Similarity	NPC231009
0.7952	Intermediate Similarity	NPC33570
0.7952	Intermediate Similarity	NPC107986
0.7952	Intermediate Similarity	NPC473478
0.7952	Intermediate Similarity	NPC21471
0.7952	Intermediate Similarity	NPC473651
0.7952	Intermediate Similarity	NPC103284
0.7952	Intermediate Similarity	NPC1083
0.7952	Intermediate Similarity	NPC66346
0.7952	Intermediate Similarity	NPC132496
0.7952	Intermediate Similarity	NPC82795
0.7952	Intermediate Similarity	NPC286338
0.7952	Intermediate Similarity	NPC283085
0.7952	Intermediate Similarity	NPC161957
0.7952	Intermediate Similarity	NPC235792
0.7952	Intermediate Similarity	NPC473669
0.7952	Intermediate Similarity	NPC223871
0.7952	Intermediate Similarity	NPC165162
0.7952	Intermediate Similarity	NPC110710
0.7927	Intermediate Similarity	NPC53867
0.7927	Intermediate Similarity	NPC116543
0.7927	Intermediate Similarity	NPC193198
0.7927	Intermediate Similarity	NPC170286
0.7927	Intermediate Similarity	NPC272814
0.7927	Intermediate Similarity	NPC215294
0.7927	Intermediate Similarity	NPC474703
0.7907	Intermediate Similarity	NPC473619
0.7907	Intermediate Similarity	NPC179394
0.7907	Intermediate Similarity	NPC129419
0.7907	Intermediate Similarity	NPC475855
0.7907	Intermediate Similarity	NPC144133
0.7907	Intermediate Similarity	NPC312042
0.7901	Intermediate Similarity	NPC255580
0.7901	Intermediate Similarity	NPC52861
0.7901	Intermediate Similarity	NPC39411
0.7887	Intermediate Similarity	NPC151648
0.7882	Intermediate Similarity	NPC475902
0.7882	Intermediate Similarity	NPC476803
0.7875	Intermediate Similarity	NPC473980
0.7875	Intermediate Similarity	NPC473981
0.7875	Intermediate Similarity	NPC471299
0.7867	Intermediate Similarity	NPC265574
0.7865	Intermediate Similarity	NPC172998
0.7865	Intermediate Similarity	NPC299396
0.7865	Intermediate Similarity	NPC301596
0.7857	Intermediate Similarity	NPC171174
0.7857	Intermediate Similarity	NPC62118
0.7857	Intermediate Similarity	NPC114694
0.7857	Intermediate Similarity	NPC69082
0.7857	Intermediate Similarity	NPC240695
0.7857	Intermediate Similarity	NPC103523
0.7857	Intermediate Similarity	NPC473687
0.7857	Intermediate Similarity	NPC204686
0.7857	Intermediate Similarity	NPC475581
0.7857	Intermediate Similarity	NPC210218
0.7857	Intermediate Similarity	NPC142117
0.7857	Intermediate Similarity	NPC134885

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 NPC123360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1845
0.2-0.3	4027
0.3-0.4	2148
0.4-0.5	646
0.5-0.6	251
0.6-0.7	52
0.7-0.8	13
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
0.7805	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1694	Approved
0.7529	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1695	Approved
0.7381	Intermediate Similarity	NPD5209	Approved
0.7363	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5785	Approved
0.7126	Intermediate Similarity	NPD5363	Approved
0.7111	Intermediate Similarity	NPD6698	Approved
0.7111	Intermediate Similarity	NPD46	Approved
0.7093	Intermediate Similarity	NPD7154	Phase 3
0.7093	Intermediate Similarity	NPD5362	Discontinued
0.697	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8039	Approved
0.6932	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4269	Approved
0.6782	Remote Similarity	NPD4270	Approved
0.6771	Remote Similarity	NPD4225	Approved
0.6744	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD5369	Approved
0.6593	Remote Similarity	NPD4251	Approved
0.6593	Remote Similarity	NPD4250	Approved
0.6588	Remote Similarity	NPD4756	Discovery
0.6559	Remote Similarity	NPD7838	Discovery
0.6522	Remote Similarity	NPD6903	Approved
0.6517	Remote Similarity	NPD5332	Approved
0.6517	Remote Similarity	NPD5331	Approved
0.6512	Remote Similarity	NPD4268	Approved
0.6512	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4271	Approved
0.6484	Remote Similarity	NPD7521	Approved
0.6484	Remote Similarity	NPD7334	Approved
0.6484	Remote Similarity	NPD5330	Approved
0.6484	Remote Similarity	NPD6684	Approved
0.6484	Remote Similarity	NPD6409	Approved
0.6484	Remote Similarity	NPD7146	Approved
0.6479	Remote Similarity	NPD6927	Phase 3
0.6477	Remote Similarity	NPD4790	Discontinued
0.6444	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6371	Approved
0.6429	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6686	Approved
0.6404	Remote Similarity	NPD6435	Approved
0.6364	Remote Similarity	NPD4821	Approved
0.6364	Remote Similarity	NPD4822	Approved
0.6364	Remote Similarity	NPD4820	Approved
0.6364	Remote Similarity	NPD4819	Approved
0.6354	Remote Similarity	NPD5282	Discontinued
0.6344	Remote Similarity	NPD6672	Approved
0.6344	Remote Similarity	NPD5737	Approved
0.6344	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7983	Approved
0.6316	Remote Similarity	NPD5693	Phase 1
0.6304	Remote Similarity	NPD6422	Discontinued
0.6289	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD2067	Discontinued
0.6277	Remote Similarity	NPD5370	Suspended
0.6263	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD6399	Phase 3
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6226	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6008	Approved
0.6211	Remote Similarity	NPD5207	Approved
0.62	Remote Similarity	NPD7640	Approved
0.62	Remote Similarity	NPD7639	Approved
0.6186	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7900	Approved
0.618	Remote Similarity	NPD5368	Approved
0.6173	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6053	Discontinued
0.6146	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6101	Approved
0.6091	Remote Similarity	NPD7115	Discovery
0.6075	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7839	Suspended
0.6027	Remote Similarity	NPD29	Approved
0.6027	Remote Similarity	NPD28	Approved
0.602	Remote Similarity	NPD6001	Approved
0.602	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD6411	Approved
0.5976	Remote Similarity	NPD7331	Phase 2
0.596	Remote Similarity	NPD5695	Phase 3
0.5949	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5696	Approved
0.5938	Remote Similarity	NPD6080	Approved
0.5938	Remote Similarity	NPD6904	Approved
0.5938	Remote Similarity	NPD6673	Approved
0.5938	Remote Similarity	NPD6051	Approved
0.5926	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD3197	Phase 1
0.5904	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD3573	Approved
0.5888	Remote Similarity	NPD2182	Approved
0.5882	Remote Similarity	NPD6648	Approved
0.5876	Remote Similarity	NPD5692	Phase 3
0.5867	Remote Similarity	NPD3172	Approved
0.5865	Remote Similarity	NPD6647	Phase 2
0.5842	Remote Similarity	NPD6084	Phase 2
0.5842	Remote Similarity	NPD6083	Phase 2
0.5833	Remote Similarity	NPD5208	Approved
0.5833	Remote Similarity	NPD5343	Approved
0.5833	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD5344	Discontinued
0.5824	Remote Similarity	NPD4695	Discontinued
0.5816	Remote Similarity	NPD6050	Approved
0.5816	Remote Similarity	NPD7515	Phase 2
0.5816	Remote Similarity	NPD5694	Approved
0.5816	Remote Similarity	NPD7637	Suspended
0.5806	Remote Similarity	NPD6110	Phase 1
0.5789	Remote Similarity	NPD3195	Phase 2
0.5789	Remote Similarity	NPD3618	Phase 1
0.5789	Remote Similarity	NPD4266	Approved
0.5789	Remote Similarity	NPD9298	Approved
0.5789	Remote Similarity	NPD3196	Approved
0.5789	Remote Similarity	NPD3194	Approved
0.5783	Remote Similarity	NPD3704	Approved
0.578	Remote Similarity	NPD2204	Approved
0.5775	Remote Similarity	NPD3174	Discontinued
0.5758	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD3665	Phase 1
0.5745	Remote Similarity	NPD3666	Approved
0.5745	Remote Similarity	NPD3668	Phase 3
0.5745	Remote Similarity	NPD3133	Approved
0.5743	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD2259	Approved
0.5714	Remote Similarity	NPD6052	Approved
0.5714	Remote Similarity	NPD2258	Approved
0.5701	Remote Similarity	NPD5697	Approved
0.5699	Remote Similarity	NPD3667	Approved
0.5663	Remote Similarity	NPD7341	Phase 2
0.5657	Remote Similarity	NPD5284	Approved
0.5657	Remote Similarity	NPD5281	Approved
0.5648	Remote Similarity	NPD6899	Approved
0.5648	Remote Similarity	NPD6011	Approved
0.5648	Remote Similarity	NPD6881	Approved
0.5648	Remote Similarity	NPD7320	Approved
0.5636	Remote Similarity	NPD6650	Approved
0.5636	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6649	Approved
0.5625	Remote Similarity	NPD6098	Approved
0.5625	Remote Similarity	NPD5279	Phase 3
0.5619	Remote Similarity	NPD7632	Discontinued
0.5618	Remote Similarity	NPD1452	Discontinued
0.5607	Remote Similarity	NPD5739	Approved
0.5607	Remote Similarity	NPD7128	Approved
0.5607	Remote Similarity	NPD6675	Approved
0.5607	Remote Similarity	NPD6402	Approved
0.5603	Remote Similarity	NPD8513	Phase 3
0.5603	Remote Similarity	NPD8517	Approved
0.5603	Remote Similarity	NPD8515	Approved
0.5603	Remote Similarity	NPD8516	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