NPASS Compound

Structure

CID154491 OpenBabel06191715522D 36 41 0 0 1 0 0 0 0 0999 V2000 8.2126 3.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7387 -0.4669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1221 -0.0158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5753 -1.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3379 -3.2988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0935 1.9603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2449 2.4502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3959 -0.9801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2450 -0.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0774 1.7518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6982 0.9805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 -2.4502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6683 1.7018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0089 2.0545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9423 0.4911 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5473 0.4902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7368 1.3991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0941 0.9808 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3964 0.9805 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5473 -0.4902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8738 0.7938 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0006 -1.9599 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6985 -1.9604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8491 0.4902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5332 0.4411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2450 0.4906 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6982 -0.9805 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8491 -0.4902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3962 1.0464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5645 -2.4604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8657 -0.4800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2610 -0.2143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -2.4500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6017 0.1384 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 14 1 0 0 0 0 4 28 1 0 0 0 0 5 34 1 0 0 0 0 6 7 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 27 1 0 0 0 0 10 14 1 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 12 22 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 30 1 0 0 0 0 14 17 2 0 0 0 0 15 2 1 1 0 0 0 15 18 1 0 0 0 0 16 11 1 1 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 26 1 0 0 0 0 18 27 1 6 0 0 0 19 27 1 6 0 0 0 20 28 1 6 0 0 0 21 15 1 1 0 0 0 21 35 1 0 0 0 0 22 25 1 0 0 0 0 22 34 1 6 0 0 0 23 28 1 0 0 0 0 23 31 2 0 0 0 0 24 29 1 6 0 0 0 24 36 1 0 0 0 0 25 29 1 6 0 0 0 25 32 1 0 0 0 0 26 33 2 0 0 0 0 26 35 1 0 0 0 0 27 3 1 6 0 0 0 28 29 1 6 0 0 0 29 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.29
Volume:	512.423
LogP:	3.232
LogD:	3.178
LogS:	-4.41
# Rotatable Bonds:	4
TPSA:	105.59
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.346
Synthetic Accessibility Score:	6.079
Fsp3:	0.862
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.904
MDCK Permeability:	4.241529313731007e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.609
Plasma Protein Binding (PPB):	58.223045349121094%
Volume Distribution (VD):	0.682
Pgp-substrate:	24.55409049987793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.804
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.637
CYP3A4-substrate:	0.493

ADMET: Excretion

Clearance (CL):	14.335
Half-life (T1/2):	0.334

ADMET: Toxicity

hERG Blockers:	0.583
Human Hepatotoxicity (H-HT):	0.908
Drug-inuced Liver Injury (DILI):	0.423
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.786
Maximum Recommended Daily Dose:	0.115
Skin Sensitization:	0.434
Carcinogencity:	0.497
Eye Corrosion:	0.007
Eye Irritation:	0.013
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC154491

Natural Product ID:	NPC154491
*Common Name:**	MKTMIPAPOLDOQT-QAYSIJLNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MKTMIPAPOLDOQT-QAYSIJLNSA-N
Standard InCHI:	InChI=1S/C29H42O7/c1-14-10-21(35-26(33)17(14)13-30)15(2)18-6-7-19-16-11-24-29(36-24)25(32)22(34-5)12-23(31)28(29,4)20(16)8-9-27(18,19)3/h15-16,18-22,24-25,30,32H,6-13H2,1-5H3/t15-,16-,18+,19-,20-,21+,22-,24+,25-,27+,28-,29-/m0/s1
SMILES:	CO[C@H]1CC(=O)[C@]2([C@]3([C@H]1O)O[C@@H]3C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H]([C@H]1CC(=C(C(=O)O1)CO)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1934583
PubChem CID:	10767792
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(75)85035-7]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	roots	n.a.	n.a.	PMID[17190461]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19056281]
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[22098611]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24079846]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26169123]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30776236]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15698	Withania somnifera	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15698	Withania somnifera	Species	Solanaceae	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	18

Activity Type	# Activity
Cell Line	12
NON-MOLECULAR	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[544070]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	10000.0	nM	PMID[544070]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	25000.0	nM	PMID[544071]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	25000.0	nM	PMID[544071]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	40000.0	nM	PMID[544073]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[544073]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[544073]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	40000.0	nM	PMID[544073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[544070]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[544070]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25000.0	nM	PMID[544071]
NPT2	Others	Unspecified		IC50	>	25000.0	nM	PMID[544071]
NPT27	Others	Unspecified		IC50	>	25000.0	nM	PMID[544071]

☑ 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 NPC154491 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	296
0.1-0.2	1713
0.2-0.3	4756
0.3-0.4	7546
0.4-0.5	12224
0.5-0.6	7274
0.6-0.7	6007
0.7-0.8	2536
0.8-0.85	257
0.85-0.9	63
0.9-0.95	16
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC268530
0.991	High Similarity	NPC159456
0.991	High Similarity	NPC4021
0.982	High Similarity	NPC251226
0.9565	High Similarity	NPC120994
0.9565	High Similarity	NPC203702
0.9554	High Similarity	NPC42673
0.9554	High Similarity	NPC230513
0.955	High Similarity	NPC55296
0.9545	High Similarity	NPC284915
0.9478	High Similarity	NPC469790
0.9397	High Similarity	NPC293112
0.9224	High Similarity	NPC11895
0.9224	High Similarity	NPC469789
0.9145	High Similarity	NPC81736
0.9145	High Similarity	NPC172154
0.9138	High Similarity	NPC170538
0.9068	High Similarity	NPC473635
0.9052	High Similarity	NPC67569
0.9018	High Similarity	NPC476163
0.8983	High Similarity	NPC8369
0.8974	High Similarity	NPC470265
0.8974	High Similarity	NPC269642
0.8974	High Similarity	NPC23786
0.8879	High Similarity	NPC475041
0.887	High Similarity	NPC58662
0.8793	High Similarity	NPC50774
0.8793	High Similarity	NPC113448
0.8793	High Similarity	NPC709
0.8761	High Similarity	NPC469656
0.8761	High Similarity	NPC474846
0.8761	High Similarity	NPC469655
0.8739	High Similarity	NPC473165
0.8707	High Similarity	NPC286528
0.8707	High Similarity	NPC20302
0.8707	High Similarity	NPC140055
0.8707	High Similarity	NPC167606
0.8707	High Similarity	NPC469684
0.8689	High Similarity	NPC231529
0.8667	High Similarity	NPC8374
0.8649	High Similarity	NPC470587
0.8644	High Similarity	NPC474370
0.8632	High Similarity	NPC478206
0.8632	High Similarity	NPC478205
0.8632	High Similarity	NPC108581
0.8571	High Similarity	NPC471783
0.8571	High Similarity	NPC9457
0.8571	High Similarity	NPC46570
0.8559	High Similarity	NPC264954
0.8547	High Similarity	NPC470492
0.8547	High Similarity	NPC478204
0.8547	High Similarity	NPC53396
0.8547	High Similarity	NPC470493
0.8547	High Similarity	NPC312824
0.8547	High Similarity	NPC183580
0.8547	High Similarity	NPC13713
0.8547	High Similarity	NPC98249
0.8537	High Similarity	NPC473593
0.8534	High Similarity	NPC147912
0.8534	High Similarity	NPC67259
0.8522	High Similarity	NPC42658
0.8522	High Similarity	NPC476964
0.8522	High Similarity	NPC269530
0.85	High Similarity	NPC153700
0.85	High Similarity	NPC88326
0.85	High Similarity	NPC107493
0.8487	Intermediate Similarity	NPC476961
0.8475	Intermediate Similarity	NPC240509
0.8475	Intermediate Similarity	NPC284707
0.8462	Intermediate Similarity	NPC270929
0.8448	Intermediate Similarity	NPC122056
0.8448	Intermediate Similarity	NPC317210
0.843	Intermediate Similarity	NPC67251
0.8417	Intermediate Similarity	NPC470779
0.8407	Intermediate Similarity	NPC180744
0.8403	Intermediate Similarity	NPC61520
0.8403	Intermediate Similarity	NPC475520
0.8403	Intermediate Similarity	NPC476960
0.84	Intermediate Similarity	NPC231240
0.8374	Intermediate Similarity	NPC473253
0.8374	Intermediate Similarity	NPC287423
0.8362	Intermediate Similarity	NPC472002
0.8361	Intermediate Similarity	NPC476729
0.8333	Intermediate Similarity	NPC273155
0.8333	Intermediate Similarity	NPC472439
0.8333	Intermediate Similarity	NPC316915
0.8333	Intermediate Similarity	NPC469916
0.8319	Intermediate Similarity	NPC251310
0.8319	Intermediate Similarity	NPC186525
0.8319	Intermediate Similarity	NPC329736
0.8306	Intermediate Similarity	NPC473620
0.8304	Intermediate Similarity	NPC159533
0.8291	Intermediate Similarity	NPC475966
0.8291	Intermediate Similarity	NPC250109
0.8291	Intermediate Similarity	NPC478212
0.8291	Intermediate Similarity	NPC25909
0.8291	Intermediate Similarity	NPC962
0.8279	Intermediate Similarity	NPC471392
0.8279	Intermediate Similarity	NPC204812
0.8279	Intermediate Similarity	NPC265557
0.8279	Intermediate Similarity	NPC473979
0.8279	Intermediate Similarity	NPC91693
0.8279	Intermediate Similarity	NPC120724
0.8279	Intermediate Similarity	NPC18945
0.8279	Intermediate Similarity	NPC105926
0.8276	Intermediate Similarity	NPC94650
0.8264	Intermediate Similarity	NPC129434
0.8261	Intermediate Similarity	NPC299590
0.825	Intermediate Similarity	NPC77689
0.825	Intermediate Similarity	NPC211093
0.825	Intermediate Similarity	NPC473636
0.825	Intermediate Similarity	NPC473274
0.825	Intermediate Similarity	NPC473839
0.8246	Intermediate Similarity	NPC187435
0.8246	Intermediate Similarity	NPC112780
0.8246	Intermediate Similarity	NPC166993
0.8246	Intermediate Similarity	NPC67321
0.824	Intermediate Similarity	NPC470880
0.824	Intermediate Similarity	NPC476966
0.8235	Intermediate Similarity	NPC134430
0.8235	Intermediate Similarity	NPC475809
0.8235	Intermediate Similarity	NPC470959
0.8235	Intermediate Similarity	NPC476965
0.8235	Intermediate Similarity	NPC243065
0.823	Intermediate Similarity	NPC65523
0.8226	Intermediate Similarity	NPC117702
0.8226	Intermediate Similarity	NPC469757
0.8226	Intermediate Similarity	NPC42399
0.8226	Intermediate Similarity	NPC471357
0.8226	Intermediate Similarity	NPC298841
0.8226	Intermediate Similarity	NPC470882
0.8226	Intermediate Similarity	NPC146456
0.822	Intermediate Similarity	NPC238667
0.822	Intermediate Similarity	NPC117712
0.8214	Intermediate Similarity	NPC295791
0.8214	Intermediate Similarity	NPC469316
0.8214	Intermediate Similarity	NPC165250
0.8211	Intermediate Similarity	NPC241456
0.8211	Intermediate Similarity	NPC24651
0.8211	Intermediate Similarity	NPC32868
0.8211	Intermediate Similarity	NPC470922
0.8211	Intermediate Similarity	NPC3381
0.8211	Intermediate Similarity	NPC318135
0.8211	Intermediate Similarity	NPC470494
0.8205	Intermediate Similarity	NPC285956
0.8205	Intermediate Similarity	NPC236217
0.8197	Intermediate Similarity	NPC222688
0.8197	Intermediate Similarity	NPC312833
0.819	Intermediate Similarity	NPC472214
0.819	Intermediate Similarity	NPC253906
0.819	Intermediate Similarity	NPC76084
0.819	Intermediate Similarity	NPC472215
0.8182	Intermediate Similarity	NPC476962
0.8182	Intermediate Similarity	NPC79579
0.8175	Intermediate Similarity	NPC173347
0.8174	Intermediate Similarity	NPC112895
0.8174	Intermediate Similarity	NPC218123
0.8174	Intermediate Similarity	NPC231278
0.8167	Intermediate Similarity	NPC473720
0.8167	Intermediate Similarity	NPC153440
0.816	Intermediate Similarity	NPC311534
0.8158	Intermediate Similarity	NPC103088
0.8158	Intermediate Similarity	NPC138908
0.8158	Intermediate Similarity	NPC323834
0.8158	Intermediate Similarity	NPC470979
0.8158	Intermediate Similarity	NPC470975
0.8158	Intermediate Similarity	NPC200957
0.8151	Intermediate Similarity	NPC16081
0.8151	Intermediate Similarity	NPC190286
0.8151	Intermediate Similarity	NPC469794
0.8151	Intermediate Similarity	NPC266728
0.8151	Intermediate Similarity	NPC72772
0.8151	Intermediate Similarity	NPC154363
0.8151	Intermediate Similarity	NPC470075
0.8151	Intermediate Similarity	NPC471127
0.8151	Intermediate Similarity	NPC49492
0.8151	Intermediate Similarity	NPC173686
0.8151	Intermediate Similarity	NPC234858
0.8151	Intermediate Similarity	NPC196931
0.8151	Intermediate Similarity	NPC64318
0.8151	Intermediate Similarity	NPC176840
0.8142	Intermediate Similarity	NPC209298
0.8142	Intermediate Similarity	NPC277074
0.8142	Intermediate Similarity	NPC474822
0.8136	Intermediate Similarity	NPC33360
0.8136	Intermediate Similarity	NPC477126
0.813	Intermediate Similarity	NPC472399
0.8125	Intermediate Similarity	NPC469327
0.812	Intermediate Similarity	NPC317107
0.812	Intermediate Similarity	NPC97939
0.812	Intermediate Similarity	NPC100329
0.812	Intermediate Similarity	NPC474229
0.812	Intermediate Similarity	NPC247031
0.812	Intermediate Similarity	NPC132790
0.8115	Intermediate Similarity	NPC470878
0.8115	Intermediate Similarity	NPC473256
0.8115	Intermediate Similarity	NPC310511
0.8115	Intermediate Similarity	NPC102822
0.8115	Intermediate Similarity	NPC477046
0.8103	Intermediate Similarity	NPC173905

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 NPC154491 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	1982
0.2-0.3	3742
0.3-0.4	2005
0.4-0.5	655
0.5-0.6	265
0.6-0.7	173
0.7-0.8	51
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
0.8707	High Similarity	NPD7115	Discovery
0.8261	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7319	Approved
0.8034	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7507	Approved
0.7778	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7640	Approved
0.7719	Intermediate Similarity	NPD7639	Approved
0.7632	Intermediate Similarity	NPD7638	Approved
0.76	Intermediate Similarity	NPD6319	Approved
0.7586	Intermediate Similarity	NPD7632	Discontinued
0.7542	Intermediate Similarity	NPD6008	Approved
0.752	Intermediate Similarity	NPD7516	Approved
0.7478	Intermediate Similarity	NPD4225	Approved
0.7462	Intermediate Similarity	NPD7736	Approved
0.744	Intermediate Similarity	NPD7328	Approved
0.744	Intermediate Similarity	NPD7327	Approved
0.7398	Intermediate Similarity	NPD4632	Approved
0.7395	Intermediate Similarity	NPD7128	Approved
0.7395	Intermediate Similarity	NPD6675	Approved
0.7395	Intermediate Similarity	NPD6402	Approved
0.7395	Intermediate Similarity	NPD5739	Approved
0.7364	Intermediate Similarity	NPD7492	Approved
0.736	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6373	Approved
0.7355	Intermediate Similarity	NPD6372	Approved
0.7323	Intermediate Similarity	NPD6054	Approved
0.7323	Intermediate Similarity	NPD6059	Approved
0.7317	Intermediate Similarity	NPD8297	Approved
0.7308	Intermediate Similarity	NPD6616	Approved
0.7295	Intermediate Similarity	NPD6371	Approved
0.7287	Intermediate Similarity	NPD8328	Phase 3
0.7273	Intermediate Similarity	NPD6881	Approved
0.7273	Intermediate Similarity	NPD7320	Approved
0.7273	Intermediate Similarity	NPD6899	Approved
0.7266	Intermediate Similarity	NPD8296	Approved
0.7266	Intermediate Similarity	NPD8033	Approved
0.7266	Intermediate Similarity	NPD8379	Approved
0.7266	Intermediate Similarity	NPD8380	Approved
0.7266	Intermediate Similarity	NPD8335	Approved
0.7266	Intermediate Similarity	NPD8378	Approved
0.7252	Intermediate Similarity	NPD7078	Approved
0.7252	Intermediate Similarity	NPD8293	Discontinued
0.7236	Intermediate Similarity	NPD6650	Approved
0.7236	Intermediate Similarity	NPD6649	Approved
0.7213	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6370	Approved
0.7203	Intermediate Similarity	NPD5344	Discontinued
0.719	Intermediate Similarity	NPD5697	Approved
0.719	Intermediate Similarity	NPD5701	Approved
0.7188	Intermediate Similarity	NPD8294	Approved
0.7188	Intermediate Similarity	NPD8377	Approved
0.7177	Intermediate Similarity	NPD6053	Discontinued
0.7154	Intermediate Similarity	NPD7290	Approved
0.7154	Intermediate Similarity	NPD4634	Approved
0.7154	Intermediate Similarity	NPD6883	Approved
0.7154	Intermediate Similarity	NPD7102	Approved
0.7154	Intermediate Similarity	NPD7604	Phase 2
0.7132	Intermediate Similarity	NPD8513	Phase 3
0.7132	Intermediate Similarity	NPD6016	Approved
0.7132	Intermediate Similarity	NPD6921	Approved
0.7132	Intermediate Similarity	NPD6015	Approved
0.7131	Intermediate Similarity	NPD6686	Approved
0.712	Intermediate Similarity	NPD8133	Approved
0.7097	Intermediate Similarity	NPD8130	Phase 1
0.7097	Intermediate Similarity	NPD6847	Approved
0.7097	Intermediate Similarity	NPD6869	Approved
0.7097	Intermediate Similarity	NPD6617	Approved
0.7087	Intermediate Similarity	NPD6009	Approved
0.7077	Intermediate Similarity	NPD5988	Approved
0.7073	Intermediate Similarity	NPD6013	Approved
0.7073	Intermediate Similarity	NPD6012	Approved
0.7073	Intermediate Similarity	NPD6014	Approved
0.7049	Intermediate Similarity	NPD6412	Phase 2
0.7043	Intermediate Similarity	NPD6399	Phase 3
0.704	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD7503	Approved
0.7	Intermediate Similarity	NPD5211	Phase 2
0.7	Intermediate Similarity	NPD5983	Phase 2
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD8517	Approved
0.6992	Remote Similarity	NPD6011	Approved
0.696	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8034	Phase 2
0.6957	Remote Similarity	NPD8035	Phase 2
0.6949	Remote Similarity	NPD4755	Approved
0.6949	Remote Similarity	NPD7902	Approved
0.693	Remote Similarity	NPD5328	Approved
0.6917	Remote Similarity	NPD6336	Discontinued
0.6885	Remote Similarity	NPD5141	Approved
0.687	Remote Similarity	NPD46	Approved
0.687	Remote Similarity	NPD6698	Approved
0.6838	Remote Similarity	NPD7748	Approved
0.6833	Remote Similarity	NPD4696	Approved
0.6833	Remote Similarity	NPD6648	Approved
0.6833	Remote Similarity	NPD5286	Approved
0.6833	Remote Similarity	NPD4700	Approved
0.6833	Remote Similarity	NPD5285	Approved
0.6815	Remote Similarity	NPD6033	Approved
0.681	Remote Similarity	NPD7637	Suspended
0.681	Remote Similarity	NPD7515	Phase 2
0.681	Remote Similarity	NPD6079	Approved
0.6807	Remote Similarity	NPD6084	Phase 2
0.6807	Remote Similarity	NPD6083	Phase 2
0.6777	Remote Similarity	NPD1700	Approved
0.6744	Remote Similarity	NPD6274	Approved
0.6726	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4697	Phase 3
0.6721	Remote Similarity	NPD5226	Approved
0.6721	Remote Similarity	NPD5225	Approved
0.6721	Remote Similarity	NPD4633	Approved
0.6721	Remote Similarity	NPD5224	Approved
0.6718	Remote Similarity	NPD7100	Approved
0.6718	Remote Similarity	NPD7101	Approved
0.6695	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD5174	Approved
0.6641	Remote Similarity	NPD6335	Approved
0.664	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4159	Approved
0.6639	Remote Similarity	NPD5223	Approved
0.6618	Remote Similarity	NPD8074	Phase 3
0.6617	Remote Similarity	NPD6909	Approved
0.6617	Remote Similarity	NPD6908	Approved
0.6612	Remote Similarity	NPD5696	Approved
0.661	Remote Similarity	NPD4202	Approved
0.661	Remote Similarity	NPD5778	Approved
0.661	Remote Similarity	NPD5779	Approved
0.6609	Remote Similarity	NPD7524	Approved
0.6583	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5221	Approved
0.6583	Remote Similarity	NPD5222	Approved
0.6581	Remote Similarity	NPD5785	Approved
0.6565	Remote Similarity	NPD6317	Approved
0.6562	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.656	Remote Similarity	NPD4768	Approved
0.656	Remote Similarity	NPD4767	Approved
0.6552	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD7260	Phase 2
0.6545	Remote Similarity	NPD6697	Approved
0.6545	Remote Similarity	NPD6115	Approved
0.6545	Remote Similarity	NPD6118	Approved
0.6545	Remote Similarity	NPD6114	Approved
0.6532	Remote Similarity	NPD4754	Approved
0.6529	Remote Similarity	NPD5173	Approved
0.6525	Remote Similarity	NPD7983	Approved
0.6522	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD6314	Approved
0.6515	Remote Similarity	NPD6313	Approved
0.65	Remote Similarity	NPD6845	Suspended
0.65	Remote Similarity	NPD5695	Phase 3
0.65	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4786	Approved
0.6489	Remote Similarity	NPD6868	Approved
0.648	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD4730	Approved
0.6457	Remote Similarity	NPD5128	Approved
0.6457	Remote Similarity	NPD4729	Approved
0.6455	Remote Similarity	NPD6116	Phase 1
0.641	Remote Similarity	NPD5737	Approved
0.641	Remote Similarity	NPD6672	Approved
0.6387	Remote Similarity	NPD5693	Phase 1
0.6387	Remote Similarity	NPD6411	Approved
0.6379	Remote Similarity	NPD7334	Approved
0.6379	Remote Similarity	NPD6409	Approved
0.6379	Remote Similarity	NPD7146	Approved
0.6379	Remote Similarity	NPD5330	Approved
0.6379	Remote Similarity	NPD7521	Approved
0.6379	Remote Similarity	NPD6684	Approved
0.6364	Remote Similarity	NPD6117	Approved
0.6357	Remote Similarity	NPD5247	Approved
0.6357	Remote Similarity	NPD5251	Approved
0.6357	Remote Similarity	NPD5248	Approved
0.6357	Remote Similarity	NPD5249	Phase 3
0.6357	Remote Similarity	NPD5250	Approved
0.6356	Remote Similarity	NPD4753	Phase 2
0.6348	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD3573	Approved
0.6316	Remote Similarity	NPD3667	Approved
0.6308	Remote Similarity	NPD5215	Approved
0.6308	Remote Similarity	NPD5216	Approved
0.6308	Remote Similarity	NPD5217	Approved
0.6303	Remote Similarity	NPD7838	Discovery
0.6293	Remote Similarity	NPD1694	Approved
0.6291	Remote Similarity	NPD7236	Approved
0.6283	Remote Similarity	NPD7525	Registered
0.6281	Remote Similarity	NPD6001	Approved
0.6277	Remote Similarity	NPD6067	Discontinued
0.6273	Remote Similarity	NPD3703	Phase 2
0.6271	Remote Similarity	NPD6903	Approved
0.6261	Remote Similarity	NPD6695	Phase 3
0.625	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD5281	Approved
0.6239	Remote Similarity	NPD5786	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