NPASS Compound

Structure

CID243305 OpenBabel06191716042D 33 37 0 0 1 0 0 0 0 0999 V2000 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 5 28 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 21 2 0 0 0 0 9 10 1 0 0 0 0 9 25 1 0 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 16 26 1 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 19 27 1 0 0 0 0 20 23 2 0 0 0 0 20 30 1 0 0 0 0 21 27 1 0 0 0 0 21 28 1 0 0 0 0 22 25 1 6 0 0 0 22 29 1 0 0 0 0 23 31 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 2 1 1 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 29 1 1 0 0 0 29 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.29
Volume:	489.336
LogP:	5.536
LogD:	3.273
LogS:	-3.632
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	4.831
Fsp3:	0.69
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.404
MDCK Permeability:	1.104154307540739e-05
Pgp-inhibitor:	0.286
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.149
Plasma Protein Binding (PPB):	99.29167938232422%
Volume Distribution (VD):	0.407
Pgp-substrate:	3.021754503250122%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.926
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.142
CYP2C9-substrate:	0.13
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.245
CYP3A4-substrate:	0.663

ADMET: Excretion

Clearance (CL):	1.401
Half-life (T1/2):	0.646

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.495
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.213
Skin Sensitization:	0.108
Carcinogencity:	0.357
Eye Corrosion:	0.003
Eye Irritation:	0.502
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC243305

Natural Product ID:	NPC243305
*Common Name:**	Dihydrocelastrol
IUPAC Name:	(2R,4aS,6aS,6aS,14aS,14bR)-10,11-dihydroxy-2,4a,6a,6a,9,14a-hexamethyl-3,4,5,6,8,13,14,14b-octahydro-1H-picene-2-carboxylic acid
Synonyms:	Dihydrocelastrol
Standard InCHIKey:	WZAUFGYINZYCKH-JJWQIEBTSA-N
Standard InCHI:	InChI=1S/C29H40O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h8,15,22,30-31H,7,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1
SMILES:	Oc1cc2c(c(c1O)C)CC=C1[C@@]2(C)CC[C@@]2([C@]1(C)CC[C@@]1([C@H]2C[C@@](C)(CC1)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1092797
PubChem CID:	10411574
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[20167482]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[27113553]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2801129]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2348	Tripterygium regelii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2348	Tripterygium regelii	Species	Celastraceae	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	5
Kd	1
Others	8

Activity Type	# Activity
Cell Line	8
Individual Protein	3
PROTEIN COMPLEX	4
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	IC50	=	21700.0	nM	PMID[463351]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3150.0	nM	PMID[463353]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	720.0	nM	PMID[463353]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	720.0	nM	PMID[463354]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3150.0	nM	PMID[463354]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	85.0	%	PMID[463357]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	11.09	%	PMID[463357]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	3.12	%	PMID[463357]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	0.79	%	PMID[463357]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	70.52	%	PMID[463352]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	40.35	%	PMID[463352]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	Inhibition	=	91.0	%	PMID[463356]
NPT21772	PROTEIN COMPLEX	GroEL/GroES	Escherichia coli	Inhibition	=	95.0	%	PMID[463356]
NPT22141	SINGLE PROTEIN	Nuclear receptor subfamily 4 group A member 1	Homo sapiens	Kd	=	870.0	nM	PMID[463357]

☑ 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 NPC243305 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	321
0.1-0.2	1456
0.2-0.3	3012
0.3-0.4	7512
0.4-0.5	10601
0.5-0.6	10489
0.6-0.7	8330
0.7-0.8	852
0.8-0.85	100
0.85-0.9	17
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9841	High Similarity	NPC476282
0.9185	High Similarity	NPC184935
0.9098	High Similarity	NPC277559
0.9091	High Similarity	NPC103082
0.9091	High Similarity	NPC43353
0.8955	High Similarity	NPC49911
0.8889	High Similarity	NPC162935
0.8889	High Similarity	NPC249340
0.8872	High Similarity	NPC293454
0.8857	High Similarity	NPC10842
0.8849	High Similarity	NPC470038
0.8768	High Similarity	NPC477873
0.8768	High Similarity	NPC469447
0.8759	High Similarity	NPC470035
0.8682	High Similarity	NPC15127
0.8676	High Similarity	NPC471152
0.8661	High Similarity	NPC241001
0.8651	High Similarity	NPC42657
0.8643	High Similarity	NPC53520
0.864	High Similarity	NPC16030
0.8571	High Similarity	NPC477207
0.8571	High Similarity	NPC199936
0.8542	High Similarity	NPC470037
0.8527	High Similarity	NPC121168
0.8516	High Similarity	NPC259703
0.8516	High Similarity	NPC32322
0.8507	High Similarity	NPC291001
0.8451	Intermediate Similarity	NPC66894
0.8451	Intermediate Similarity	NPC8102
0.845	Intermediate Similarity	NPC154696
0.845	Intermediate Similarity	NPC253627
0.8438	Intermediate Similarity	NPC478121
0.8385	Intermediate Similarity	NPC11250
0.8382	Intermediate Similarity	NPC18982
0.8382	Intermediate Similarity	NPC475627
0.8382	Intermediate Similarity	NPC475346
0.8382	Intermediate Similarity	NPC475457
0.8382	Intermediate Similarity	NPC111845
0.8382	Intermediate Similarity	NPC138472
0.8372	Intermediate Similarity	NPC164852
0.8359	Intermediate Similarity	NPC93071
0.8357	Intermediate Similarity	NPC27518
0.8357	Intermediate Similarity	NPC304110
0.8345	Intermediate Similarity	NPC182249
0.8322	Intermediate Similarity	NPC258856
0.8322	Intermediate Similarity	NPC75295
0.8321	Intermediate Similarity	NPC471187
0.8321	Intermediate Similarity	NPC198014
0.8288	Intermediate Similarity	NPC473680
0.8288	Intermediate Similarity	NPC475311
0.8288	Intermediate Similarity	NPC473579
0.8288	Intermediate Similarity	NPC475454
0.8288	Intermediate Similarity	NPC118033
0.8286	Intermediate Similarity	NPC155192
0.8286	Intermediate Similarity	NPC271494
0.8286	Intermediate Similarity	NPC473591
0.8268	Intermediate Similarity	NPC471668
0.8264	Intermediate Similarity	NPC474991
0.8261	Intermediate Similarity	NPC153088
0.8261	Intermediate Similarity	NPC472804
0.8261	Intermediate Similarity	NPC173569
0.8261	Intermediate Similarity	NPC477874
0.8261	Intermediate Similarity	NPC279463
0.8258	Intermediate Similarity	NPC181334
0.8252	Intermediate Similarity	NPC126707
0.8248	Intermediate Similarity	NPC49742
0.8244	Intermediate Similarity	NPC471794
0.8244	Intermediate Similarity	NPC176208
0.8235	Intermediate Similarity	NPC18798
0.8231	Intermediate Similarity	NPC475579
0.8231	Intermediate Similarity	NPC473773
0.8227	Intermediate Similarity	NPC3218
0.8219	Intermediate Similarity	NPC142654
0.8217	Intermediate Similarity	NPC126002
0.8214	Intermediate Similarity	NPC469681
0.8214	Intermediate Similarity	NPC469680
0.8214	Intermediate Similarity	NPC471974
0.8214	Intermediate Similarity	NPC230811
0.8212	Intermediate Similarity	NPC185617
0.8207	Intermediate Similarity	NPC470757
0.8201	Intermediate Similarity	NPC249817
0.8195	Intermediate Similarity	NPC87985
0.8195	Intermediate Similarity	NPC137750
0.8194	Intermediate Similarity	NPC84786
0.8182	Intermediate Similarity	NPC25491
0.8175	Intermediate Similarity	NPC317869
0.8169	Intermediate Similarity	NPC272907
0.8169	Intermediate Similarity	NPC2681
0.8154	Intermediate Similarity	NPC190501
0.8154	Intermediate Similarity	NPC318552
0.8151	Intermediate Similarity	NPC477206
0.8143	Intermediate Similarity	NPC22676
0.8143	Intermediate Similarity	NPC475482
0.8143	Intermediate Similarity	NPC198621
0.8143	Intermediate Similarity	NPC216940
0.8138	Intermediate Similarity	NPC191899
0.8138	Intermediate Similarity	NPC58752
0.8138	Intermediate Similarity	NPC246229
0.8134	Intermediate Similarity	NPC71610
0.812	Intermediate Similarity	NPC471927
0.8116	Intermediate Similarity	NPC4170
0.8112	Intermediate Similarity	NPC235557
0.8106	Intermediate Similarity	NPC478058
0.8102	Intermediate Similarity	NPC258073
0.8099	Intermediate Similarity	NPC473612
0.8099	Intermediate Similarity	NPC476534
0.8099	Intermediate Similarity	NPC471853
0.8095	Intermediate Similarity	NPC471179
0.8088	Intermediate Similarity	NPC117899
0.8082	Intermediate Similarity	NPC127046
0.808	Intermediate Similarity	NPC141782
0.8074	Intermediate Similarity	NPC69424
0.8074	Intermediate Similarity	NPC72667
0.8074	Intermediate Similarity	NPC78364
0.8074	Intermediate Similarity	NPC476536
0.8074	Intermediate Similarity	NPC176130
0.8074	Intermediate Similarity	NPC84672
0.8071	Intermediate Similarity	NPC7464
0.8056	Intermediate Similarity	NPC26045
0.8054	Intermediate Similarity	NPC205392
0.8054	Intermediate Similarity	NPC105942
0.8042	Intermediate Similarity	NPC35212
0.8028	Intermediate Similarity	NPC79372
0.8016	Intermediate Similarity	NPC260323
0.8016	Intermediate Similarity	NPC176279
0.8015	Intermediate Similarity	NPC193203
0.8015	Intermediate Similarity	NPC229894
0.8	Intermediate Similarity	NPC328694
0.8	Intermediate Similarity	NPC254492
0.8	Intermediate Similarity	NPC307205
0.8	Intermediate Similarity	NPC252343
0.7987	Intermediate Similarity	NPC124842
0.7986	Intermediate Similarity	NPC310621
0.7986	Intermediate Similarity	NPC252133
0.7986	Intermediate Similarity	NPC248068
0.7985	Intermediate Similarity	NPC199273
0.7972	Intermediate Similarity	NPC29599
0.7972	Intermediate Similarity	NPC472801
0.7972	Intermediate Similarity	NPC172311
0.7969	Intermediate Similarity	NPC268160
0.7958	Intermediate Similarity	NPC473479
0.7958	Intermediate Similarity	NPC289358
0.7958	Intermediate Similarity	NPC165191
0.7958	Intermediate Similarity	NPC114333
0.7958	Intermediate Similarity	NPC46242
0.7958	Intermediate Similarity	NPC245760
0.7958	Intermediate Similarity	NPC473779
0.7958	Intermediate Similarity	NPC248287
0.7958	Intermediate Similarity	NPC477849
0.7958	Intermediate Similarity	NPC234548
0.7958	Intermediate Similarity	NPC23667
0.7958	Intermediate Similarity	NPC297797
0.7958	Intermediate Similarity	NPC91887
0.7958	Intermediate Similarity	NPC51531
0.7958	Intermediate Similarity	NPC42384
0.7958	Intermediate Similarity	NPC50615
0.7958	Intermediate Similarity	NPC28592
0.7958	Intermediate Similarity	NPC149773
0.7958	Intermediate Similarity	NPC157284
0.7958	Intermediate Similarity	NPC469857
0.7958	Intermediate Similarity	NPC5014
0.7956	Intermediate Similarity	NPC131684
0.7956	Intermediate Similarity	NPC303910
0.7956	Intermediate Similarity	NPC276238
0.7956	Intermediate Similarity	NPC171460
0.7953	Intermediate Similarity	NPC250323
0.7939	Intermediate Similarity	NPC473974
0.7939	Intermediate Similarity	NPC258366
0.7939	Intermediate Similarity	NPC31296
0.7939	Intermediate Similarity	NPC79933
0.7937	Intermediate Similarity	NPC13482
0.7937	Intermediate Similarity	NPC222084
0.7929	Intermediate Similarity	NPC27394
0.7929	Intermediate Similarity	NPC477594
0.7929	Intermediate Similarity	NPC471913
0.7926	Intermediate Similarity	NPC137416
0.7923	Intermediate Similarity	NPC278652
0.791	Intermediate Similarity	NPC53567
0.791	Intermediate Similarity	NPC275145
0.7907	Intermediate Similarity	NPC35797
0.7907	Intermediate Similarity	NPC147179
0.7907	Intermediate Similarity	NPC192948
0.7905	Intermediate Similarity	NPC471852
0.7902	Intermediate Similarity	NPC294330
0.7899	Intermediate Similarity	NPC108129
0.7891	Intermediate Similarity	NPC148969
0.7883	Intermediate Similarity	NPC201069
0.7881	Intermediate Similarity	NPC62051
0.7879	Intermediate Similarity	NPC475245
0.7872	Intermediate Similarity	NPC477596
0.7862	Intermediate Similarity	NPC477209
0.7852	Intermediate Similarity	NPC224342
0.7847	Intermediate Similarity	NPC473527
0.7846	Intermediate Similarity	NPC308311
0.7846	Intermediate Similarity	NPC219112
0.7846	Intermediate Similarity	NPC477137
0.7846	Intermediate Similarity	NPC308828
0.7846	Intermediate Similarity	NPC38893
0.7842	Intermediate Similarity	NPC471851
0.7842	Intermediate Similarity	NPC312341

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 NPC243305 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	898
0.2-0.3	1531
0.3-0.4	2852
0.4-0.5	2124
0.5-0.6	1089
0.6-0.7	350
0.7-0.8	21
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD8166	Discontinued
0.8154	Intermediate Similarity	NPD2932	Approved
0.8154	Intermediate Similarity	NPD3019	Approved
0.7971	Intermediate Similarity	NPD6663	Approved
0.7941	Intermediate Similarity	NPD5736	Approved
0.7823	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD3021	Approved
0.7717	Intermediate Similarity	NPD3022	Approved
0.7687	Intermediate Similarity	NPD3023	Approved
0.7687	Intermediate Similarity	NPD3026	Approved
0.7671	Intermediate Similarity	NPD7003	Approved
0.7669	Intermediate Similarity	NPD3024	Approved
0.7669	Intermediate Similarity	NPD3025	Approved
0.7639	Intermediate Similarity	NPD5405	Approved
0.7639	Intermediate Similarity	NPD5406	Approved
0.7639	Intermediate Similarity	NPD5404	Approved
0.7639	Intermediate Similarity	NPD5408	Approved
0.7386	Intermediate Similarity	NPD7458	Discontinued
0.7372	Intermediate Similarity	NPD3092	Approved
0.7343	Intermediate Similarity	NPD8032	Phase 2
0.7338	Intermediate Similarity	NPD1283	Approved
0.7333	Intermediate Similarity	NPD3091	Approved
0.7329	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4060	Phase 1
0.7292	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3620	Phase 2
0.7286	Intermediate Similarity	NPD3094	Phase 2
0.7285	Intermediate Similarity	NPD7390	Discontinued
0.7273	Intermediate Similarity	NPD7635	Approved
0.7246	Intermediate Similarity	NPD1201	Approved
0.7239	Intermediate Similarity	NPD7228	Approved
0.7234	Intermediate Similarity	NPD258	Approved
0.7234	Intermediate Similarity	NPD257	Approved
0.7233	Intermediate Similarity	NPD6234	Discontinued
0.7226	Intermediate Similarity	NPD4059	Approved
0.7203	Intermediate Similarity	NPD7095	Approved
0.72	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5951	Approved
0.7163	Intermediate Similarity	NPD1470	Approved
0.7154	Intermediate Similarity	NPD2342	Discontinued
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7134	Intermediate Similarity	NPD37	Approved
0.7122	Intermediate Similarity	NPD1281	Approved
0.7105	Intermediate Similarity	NPD3300	Phase 2
0.7101	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3095	Discontinued
0.7101	Intermediate Similarity	NPD4626	Approved
0.7095	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4110	Phase 3
0.7078	Intermediate Similarity	NPD6273	Approved
0.7076	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7473	Discontinued
0.7055	Intermediate Similarity	NPD826	Approved
0.7055	Intermediate Similarity	NPD825	Approved
0.7044	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD1809	Phase 2
0.7039	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD3020	Approved
0.7007	Intermediate Similarity	NPD6355	Discontinued
0.7006	Intermediate Similarity	NPD7028	Phase 2
0.7	Intermediate Similarity	NPD4967	Phase 2
0.7	Intermediate Similarity	NPD4966	Approved
0.7	Intermediate Similarity	NPD4965	Approved
0.6994	Remote Similarity	NPD6232	Discontinued
0.697	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD9569	Approved
0.6939	Remote Similarity	NPD943	Approved
0.6939	Remote Similarity	NPD2979	Phase 3
0.6939	Remote Similarity	NPD4140	Approved
0.6933	Remote Similarity	NPD6099	Approved
0.6933	Remote Similarity	NPD2935	Discontinued
0.6933	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD1164	Approved
0.6918	Remote Similarity	NPD6798	Discontinued
0.6918	Remote Similarity	NPD3764	Approved
0.6917	Remote Similarity	NPD4750	Phase 3
0.6912	Remote Similarity	NPD2629	Approved
0.6906	Remote Similarity	NPD1651	Approved
0.6901	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD275	Approved
0.6892	Remote Similarity	NPD274	Approved
0.6871	Remote Similarity	NPD259	Phase 1
0.685	Remote Similarity	NPD288	Approved
0.6849	Remote Similarity	NPD9536	Phase 1
0.6849	Remote Similarity	NPD9537	Phase 1
0.6839	Remote Similarity	NPD2421	Approved
0.6839	Remote Similarity	NPD2420	Approved
0.6835	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD9269	Phase 2
0.6825	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2438	Suspended
0.6818	Remote Similarity	NPD6190	Approved
0.6815	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2797	Approved
0.68	Remote Similarity	NPD7097	Phase 1
0.6797	Remote Similarity	NPD6674	Discontinued
0.6795	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4093	Discontinued
0.6786	Remote Similarity	NPD5691	Approved
0.6786	Remote Similarity	NPD5844	Phase 1
0.6784	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2605	Approved
0.6781	Remote Similarity	NPD2606	Approved
0.6779	Remote Similarity	NPD555	Phase 2
0.6776	Remote Similarity	NPD7266	Discontinued
0.6776	Remote Similarity	NPD2346	Discontinued
0.6772	Remote Similarity	NPD844	Approved
0.6772	Remote Similarity	NPD2860	Approved
0.6772	Remote Similarity	NPD2859	Approved
0.677	Remote Similarity	NPD1465	Phase 2
0.6765	Remote Similarity	NPD7240	Approved
0.6755	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2799	Discontinued
0.6753	Remote Similarity	NPD3750	Approved
0.6746	Remote Similarity	NPD845	Approved
0.6738	Remote Similarity	NPD1751	Approved
0.6738	Remote Similarity	NPD2286	Discontinued
0.6735	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5155	Approved
0.6735	Remote Similarity	NPD5156	Approved
0.6735	Remote Similarity	NPD7008	Discontinued
0.6733	Remote Similarity	NPD4097	Suspended
0.6731	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7199	Phase 2
0.6715	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2531	Phase 2
0.6711	Remote Similarity	NPD4477	Approved
0.6711	Remote Similarity	NPD4476	Approved
0.6705	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD2934	Approved
0.6693	Remote Similarity	NPD2933	Approved
0.6691	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3268	Approved
0.6688	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3645	Discontinued
0.6667	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD3594	Approved
0.6667	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD5735	Approved
0.6667	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD5762	Approved
0.6667	Remote Similarity	NPD3595	Approved
0.6647	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4628	Phase 3
0.6644	Remote Similarity	NPD4624	Approved
0.6627	Remote Similarity	NPD6959	Discontinued
0.6625	Remote Similarity	NPD3226	Approved
0.6623	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6696	Suspended
0.6619	Remote Similarity	NPD4198	Discontinued
0.6619	Remote Similarity	NPD255	Approved
0.6619	Remote Similarity	NPD256	Approved
0.6604	Remote Similarity	NPD7427	Discontinued
0.66	Remote Similarity	NPD6346	Approved
0.6599	Remote Similarity	NPD3635	Approved
0.6599	Remote Similarity	NPD3636	Approved
0.6599	Remote Similarity	NPD3637	Approved
0.6597	Remote Similarity	NPD1608	Approved
0.6594	Remote Similarity	NPD5283	Phase 1
0.659	Remote Similarity	NPD8313	Approved
0.659	Remote Similarity	NPD8312	Approved
0.6585	Remote Similarity	NPD7768	Phase 2
0.6581	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7985	Registered
0.6577	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD228	Approved
0.6564	Remote Similarity	NPD7819	Suspended
0.6556	Remote Similarity	NPD3657	Discovery
0.6552	Remote Similarity	NPD1755	Approved
0.6552	Remote Similarity	NPD5327	Phase 3
0.6549	Remote Similarity	NPD9268	Approved
0.6543	Remote Similarity	NPD6873	Phase 2
0.6543	Remote Similarity	NPD6677	Suspended
0.6538	Remote Similarity	NPD3400	Discontinued
0.6536	Remote Similarity	NPD7742	Approved
0.6536	Remote Similarity	NPD7743	Approved
0.6533	Remote Similarity	NPD6233	Phase 2
0.6531	Remote Similarity	NPD2195	Approved
0.6531	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD2194	Approved
0.6528	Remote Similarity	NPD1611	Approved
0.6522	Remote Similarity	NPD3455	Phase 2
0.6513	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1778	Approved
0.6503	Remote Similarity	NPD4589	Approved
0.6494	Remote Similarity	NPD9570	Approved
0.6494	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD7229	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