NPASS Compound

Structure

NPC153440 OpenBabel07101719252D 34 38 0 0 1 0 0 0 0 0999 V2000 -1.5645 4.8151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2888 5.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1514 1.4402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4117 2.6007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6772 0.8546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9432 3.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9432 2.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0994 3.5751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0994 0.6520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2555 0.1648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5679 2.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7241 1.6263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3653 -0.7883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3963 -0.8901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0430 3.2101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8404 4.1631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0862 4.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0994 1.6263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4117 1.6263 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4117 0.6520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2555 3.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3189 2.5581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8103 3.8123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7241 0.6520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2555 2.1135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7241 0.6520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5679 0.1648 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 2.4117 3.5751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7370 4.1134 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3761 -0.0721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5369 0.0629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9267 -0.3011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6077 2.8592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 24 1 0 0 0 0 6 7 1 0 0 0 0 6 8 2 0 0 0 0 7 18 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 18 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 17 2 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 6 0 0 0 20 27 1 1 0 0 0 21 25 1 0 0 0 0 21 29 2 0 0 0 0 22 26 1 1 0 0 0 22 34 1 0 0 0 0 23 30 2 0 0 0 0 23 34 1 0 0 0 0 24 27 1 6 0 0 0 25 4 1 6 0 0 0 26 5 1 6 0 0 0 26 28 1 0 0 0 0 26 31 1 0 0 0 0 27 32 1 1 0 0 0 28 24 1 6 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.27
Volume:	489.621
LogP:	2.594
LogD:	1.922
LogS:	-4.458
# Rotatable Bonds:	2
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.534
Synthetic Accessibility Score:	5.349
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.821
MDCK Permeability:	2.2857053409097716e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.939
Human Intestinal Absorption (HIA):	0.06
20% Bioavailability (F20%):	0.398
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.988
Plasma Protein Binding (PPB):	84.81425476074219%
Volume Distribution (VD):	1.062
Pgp-substrate:	10.565983772277832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.625
CYP2C19-inhibitor:	0.303
CYP2C19-substrate:	0.742
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.847
CYP3A4-substrate:	0.932

ADMET: Excretion

Clearance (CL):	4.23
Half-life (T1/2):	0.725

ADMET: Toxicity

hERG Blockers:	0.237
Human Hepatotoxicity (H-HT):	0.662
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.28
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.912
Carcinogencity:	0.977
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC153440

Natural Product ID:	NPC153440
*Common Name:**	Withanolide F
IUPAC Name:	(2R)-2-[(1S)-1-[(8R,9S,10R,13S,14R,17S)-14,17-dihydroxy-10,13-dimethyl-1-oxo-4,7,8,9,11,12,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-1-hydroxyethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
Synonyms:	Withanolide F
Standard InCHIKey:	GQHHHBATDOXAEP-MEZCUPPISA-N
Standard InCHI:	InChI=1S/C28H38O6/c1-16-15-22(34-23(30)17(16)2)26(5,31)28(33)14-13-27(32)20-10-9-18-7-6-8-21(29)25(18,4)19(20)11-12-24(27,28)3/h6,8-9,19-20,22,31-33H,7,10-15H2,1-5H3/t19-,20+,22+,24-,25-,26-,27+,28-/m0/s1
SMILES:	CC1=C(C)C(=O)O[C@H](C1)[C@@](C)([C@@]1(CC[C@]2([C@@H]3CC=C4CC=CC(=O)[C@]4(C)[C@H]3CC[C@]12C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488913
PubChem CID:	44562999
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
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[18952419]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23316950]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28617598]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30649869]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	Whole Fruits	n.a.	n.a.	PMID[32159343]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28734	Physalis peruviana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13927	Withania coagulans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28734	Physalis peruviana	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	10
Others	6

Activity Type	# Activity
Cell Line	10
Individual Protein	1
Organism	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	10900.0	nM	PMID[456514]
NPT71	Cell Line	HEK293	Homo sapiens	Survival	=	100.0	%	PMID[456514]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	=	100.0	%	PMID[456514]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	84.6	%	PMID[456514]
NPT2601	Individual Protein	NF-kappaB inhibitor alpha	Homo sapiens	IC50	>	50000.0	nM	PMID[456515]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	130.0	nM	PMID[456516]
NPT1629	Cell Line	CWR22R	Homo sapiens	IC50	=	70.0	nM	PMID[456516]
NPT369	Cell Line	ACHN	Homo sapiens	IC50	>	2000.0	nM	PMID[456516]
NPT387	Cell Line	M14	Homo sapiens	IC50	>	2000.0	nM	PMID[456516]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	2000.0	nM	PMID[456516]
NPT859	Cell Line	HFF	Homo sapiens	IC50	>	2000.0	nM	PMID[456516]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	24.9	%	PMID[456513]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	18.2	%	PMID[456513]
NPT2	Others	Unspecified		IC50	=	5700.0	nM	PMID[456514]
NPT2	Others	Unspecified		Inhibition	=	90.8	%	PMID[456514]
NPT2	Others	Unspecified		IC50	=	2000.0	nM	PMID[456515]

☑ 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 NPC153440 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	230
0.1-0.2	1251
0.2-0.3	3969
0.3-0.4	7076
0.4-0.5	13158
0.5-0.6	6857
0.6-0.7	7119
0.7-0.8	2775
0.8-0.85	200
0.85-0.9	43
0.9-0.95	4
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC5292
0.9818	High Similarity	NPC79579
0.9818	High Similarity	NPC474585
0.9815	High Similarity	NPC190286
0.9727	High Similarity	NPC270850
0.9727	High Similarity	NPC305260
0.9643	High Similarity	NPC107493
0.9554	High Similarity	NPC46570
0.9455	High Similarity	NPC176840
0.9052	High Similarity	NPC473979
0.9035	High Similarity	NPC475041
0.9009	High Similarity	NPC236217
0.8889	High Similarity	NPC469789
0.885	High Similarity	NPC474181
0.8839	High Similarity	NPC191620
0.8829	High Similarity	NPC473627
0.8829	High Similarity	NPC37116
0.8803	High Similarity	NPC170538
0.8803	High Similarity	NPC269642
0.8739	High Similarity	NPC473635
0.8739	High Similarity	NPC293112
0.8729	High Similarity	NPC11895
0.8718	High Similarity	NPC67569
0.8678	High Similarity	NPC231529
0.8667	High Similarity	NPC287423
0.8661	High Similarity	NPC197428
0.8655	High Similarity	NPC172154
0.8655	High Similarity	NPC81736
0.8655	High Similarity	NPC8369
0.8655	High Similarity	NPC8374
0.8644	High Similarity	NPC23786
0.8644	High Similarity	NPC470265
0.8632	High Similarity	NPC474370
0.8607	High Similarity	NPC173347
0.8596	High Similarity	NPC194100
0.8595	High Similarity	NPC245094
0.8584	High Similarity	NPC470961
0.8571	High Similarity	NPC204812
0.8559	High Similarity	NPC310511
0.8547	High Similarity	NPC264954
0.8537	High Similarity	NPC471855
0.8532	High Similarity	NPC475320
0.8522	High Similarity	NPC470953
0.85	High Similarity	NPC241456
0.85	High Similarity	NPC32868
0.8496	Intermediate Similarity	NPC29133
0.8487	Intermediate Similarity	NPC88326
0.8487	Intermediate Similarity	NPC153700
0.8482	Intermediate Similarity	NPC472825
0.848	Intermediate Similarity	NPC158350
0.8475	Intermediate Similarity	NPC476961
0.8462	Intermediate Similarity	NPC475913
0.8462	Intermediate Similarity	NPC186525
0.8462	Intermediate Similarity	NPC50774
0.8462	Intermediate Similarity	NPC257457
0.8462	Intermediate Similarity	NPC311554
0.8462	Intermediate Similarity	NPC709
0.8455	Intermediate Similarity	NPC213634
0.8448	Intermediate Similarity	NPC148458
0.8448	Intermediate Similarity	NPC64318
0.8443	Intermediate Similarity	NPC311534
0.8435	Intermediate Similarity	NPC25909
0.8435	Intermediate Similarity	NPC962
0.8435	Intermediate Similarity	NPC250109
0.8435	Intermediate Similarity	NPC471204
0.843	Intermediate Similarity	NPC159499
0.8417	Intermediate Similarity	NPC120724
0.8417	Intermediate Similarity	NPC6193
0.8407	Intermediate Similarity	NPC284828
0.8407	Intermediate Similarity	NPC472216
0.8407	Intermediate Similarity	NPC173905
0.8407	Intermediate Similarity	NPC5475
0.8403	Intermediate Similarity	NPC202051
0.8393	Intermediate Similarity	NPC144459
0.839	Intermediate Similarity	NPC472667
0.839	Intermediate Similarity	NPC475520
0.839	Intermediate Similarity	NPC474179
0.839	Intermediate Similarity	NPC473203
0.839	Intermediate Similarity	NPC475834
0.839	Intermediate Similarity	NPC61520
0.8387	Intermediate Similarity	NPC155529
0.8376	Intermediate Similarity	NPC20302
0.8376	Intermediate Similarity	NPC140055
0.8376	Intermediate Similarity	NPC239273
0.8376	Intermediate Similarity	NPC167606
0.8376	Intermediate Similarity	NPC470492
0.8376	Intermediate Similarity	NPC286528
0.8374	Intermediate Similarity	NPC221414
0.8374	Intermediate Similarity	NPC471407
0.8364	Intermediate Similarity	NPC22388
0.8362	Intermediate Similarity	NPC67259
0.8362	Intermediate Similarity	NPC147912
0.8362	Intermediate Similarity	NPC326542
0.8361	Intermediate Similarity	NPC470882
0.8361	Intermediate Similarity	NPC473253
0.8361	Intermediate Similarity	NPC473265
0.8348	Intermediate Similarity	NPC221144
0.8348	Intermediate Similarity	NPC152117
0.8348	Intermediate Similarity	NPC475524
0.8348	Intermediate Similarity	NPC126691
0.8348	Intermediate Similarity	NPC100267
0.8348	Intermediate Similarity	NPC234042
0.8348	Intermediate Similarity	NPC269530
0.8333	Intermediate Similarity	NPC41551
0.8333	Intermediate Similarity	NPC5103
0.8319	Intermediate Similarity	NPC65941
0.8305	Intermediate Similarity	NPC329736
0.8305	Intermediate Similarity	NPC475372
0.8304	Intermediate Similarity	NPC323834
0.8293	Intermediate Similarity	NPC473888
0.8291	Intermediate Similarity	NPC266728
0.8291	Intermediate Similarity	NPC49492
0.8291	Intermediate Similarity	NPC476963
0.8276	Intermediate Similarity	NPC255017
0.8276	Intermediate Similarity	NPC469463
0.8276	Intermediate Similarity	NPC469454
0.8276	Intermediate Similarity	NPC469496
0.8276	Intermediate Similarity	NPC317210
0.8264	Intermediate Similarity	NPC27363
0.8261	Intermediate Similarity	NPC179798
0.8261	Intermediate Similarity	NPC470076
0.8261	Intermediate Similarity	NPC304180
0.8246	Intermediate Similarity	NPC41405
0.8235	Intermediate Similarity	NPC475775
0.8235	Intermediate Similarity	NPC476529
0.8235	Intermediate Similarity	NPC473636
0.8235	Intermediate Similarity	NPC77689
0.8235	Intermediate Similarity	NPC476960
0.8235	Intermediate Similarity	NPC312536
0.8235	Intermediate Similarity	NPC278681
0.823	Intermediate Similarity	NPC475294
0.823	Intermediate Similarity	NPC91034
0.8226	Intermediate Similarity	NPC476966
0.8226	Intermediate Similarity	NPC470880
0.8226	Intermediate Similarity	NPC473593
0.822	Intermediate Similarity	NPC183580
0.822	Intermediate Similarity	NPC134430
0.822	Intermediate Similarity	NPC476965
0.822	Intermediate Similarity	NPC473968
0.822	Intermediate Similarity	NPC312824
0.822	Intermediate Similarity	NPC284068
0.822	Intermediate Similarity	NPC470493
0.822	Intermediate Similarity	NPC470959
0.822	Intermediate Similarity	NPC471854
0.822	Intermediate Similarity	NPC476959
0.8205	Intermediate Similarity	NPC178289
0.8205	Intermediate Similarity	NPC471398
0.8205	Intermediate Similarity	NPC473898
0.8198	Intermediate Similarity	NPC473424
0.8197	Intermediate Similarity	NPC469790
0.8197	Intermediate Similarity	NPC473255
0.819	Intermediate Similarity	NPC470063
0.819	Intermediate Similarity	NPC277769
0.819	Intermediate Similarity	NPC207251
0.8182	Intermediate Similarity	NPC222688
0.8174	Intermediate Similarity	NPC50223
0.8174	Intermediate Similarity	NPC5284
0.8167	Intermediate Similarity	NPC476962
0.8167	Intermediate Similarity	NPC154491
0.8167	Intermediate Similarity	NPC114939
0.8167	Intermediate Similarity	NPC41123
0.8167	Intermediate Similarity	NPC145074
0.8167	Intermediate Similarity	NPC112936
0.8167	Intermediate Similarity	NPC107338
0.8167	Intermediate Similarity	NPC143755
0.8167	Intermediate Similarity	NPC251226
0.8167	Intermediate Similarity	NPC268530
0.8167	Intermediate Similarity	NPC109607
0.8158	Intermediate Similarity	NPC472217
0.8158	Intermediate Similarity	NPC472219
0.8158	Intermediate Similarity	NPC329417
0.8158	Intermediate Similarity	NPC189075
0.8158	Intermediate Similarity	NPC177064
0.8158	Intermediate Similarity	NPC472218
0.8158	Intermediate Similarity	NPC275539
0.8151	Intermediate Similarity	NPC473720
0.8151	Intermediate Similarity	NPC16701
0.8151	Intermediate Similarity	NPC288679
0.8145	Intermediate Similarity	NPC473620
0.8142	Intermediate Similarity	NPC231530
0.8142	Intermediate Similarity	NPC96377
0.8142	Intermediate Similarity	NPC278628
0.8142	Intermediate Similarity	NPC60681
0.814	Intermediate Similarity	NPC75616
0.8136	Intermediate Similarity	NPC270929
0.8136	Intermediate Similarity	NPC106228
0.8136	Intermediate Similarity	NPC298278
0.8136	Intermediate Similarity	NPC138372
0.8136	Intermediate Similarity	NPC196931
0.813	Intermediate Similarity	NPC250556
0.813	Intermediate Similarity	NPC469750
0.8125	Intermediate Similarity	NPC474775
0.8125	Intermediate Similarity	NPC245017
0.8125	Intermediate Similarity	NPC127656
0.8125	Intermediate Similarity	NPC236390
0.8125	Intermediate Similarity	NPC130447
0.812	Intermediate Similarity	NPC122056
0.812	Intermediate Similarity	NPC56448
0.8115	Intermediate Similarity	NPC55602
0.811	Intermediate Similarity	NPC296617

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 NPC153440 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	1473
0.2-0.3	3640
0.3-0.4	2442
0.4-0.5	852
0.5-0.6	255
0.6-0.7	159
0.7-0.8	121
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8376	Intermediate Similarity	NPD7115	Discovery
0.8276	Intermediate Similarity	NPD4632	Approved
0.819	Intermediate Similarity	NPD6053	Discontinued
0.819	Intermediate Similarity	NPD8297	Approved
0.8167	Intermediate Similarity	NPD6319	Approved
0.8158	Intermediate Similarity	NPD6881	Approved
0.8158	Intermediate Similarity	NPD6899	Approved
0.813	Intermediate Similarity	NPD7507	Approved
0.807	Intermediate Similarity	NPD5697	Approved
0.8017	Intermediate Similarity	NPD7290	Approved
0.8017	Intermediate Similarity	NPD6883	Approved
0.8017	Intermediate Similarity	NPD7102	Approved
0.7982	Intermediate Similarity	NPD7128	Approved
0.7982	Intermediate Similarity	NPD6675	Approved
0.7982	Intermediate Similarity	NPD6402	Approved
0.7982	Intermediate Similarity	NPD5739	Approved
0.7951	Intermediate Similarity	NPD7503	Approved
0.7949	Intermediate Similarity	NPD6869	Approved
0.7949	Intermediate Similarity	NPD6649	Approved
0.7949	Intermediate Similarity	NPD6847	Approved
0.7949	Intermediate Similarity	NPD6650	Approved
0.7949	Intermediate Similarity	NPD8130	Phase 1
0.7949	Intermediate Similarity	NPD6617	Approved
0.7937	Intermediate Similarity	NPD7319	Approved
0.7931	Intermediate Similarity	NPD6013	Approved
0.7931	Intermediate Similarity	NPD6014	Approved
0.7931	Intermediate Similarity	NPD6012	Approved
0.7917	Intermediate Similarity	NPD6009	Approved
0.7903	Intermediate Similarity	NPD7492	Approved
0.7881	Intermediate Similarity	NPD6882	Approved
0.7869	Intermediate Similarity	NPD6054	Approved
0.7857	Intermediate Similarity	NPD7736	Approved
0.7845	Intermediate Similarity	NPD6011	Approved
0.7845	Intermediate Similarity	NPD7320	Approved
0.784	Intermediate Similarity	NPD6616	Approved
0.7826	Intermediate Similarity	NPD6008	Approved
0.7823	Intermediate Similarity	NPD7604	Phase 2
0.7805	Intermediate Similarity	NPD5983	Phase 2
0.7778	Intermediate Similarity	NPD6373	Approved
0.7778	Intermediate Similarity	NPD6372	Approved
0.7778	Intermediate Similarity	NPD7078	Approved
0.7768	Intermediate Similarity	NPD7638	Approved
0.7759	Intermediate Similarity	NPD6412	Phase 2
0.7759	Intermediate Similarity	NPD5701	Approved
0.7742	Intermediate Similarity	NPD6370	Approved
0.7719	Intermediate Similarity	NPD5211	Phase 2
0.7712	Intermediate Similarity	NPD4634	Approved
0.7699	Intermediate Similarity	NPD7639	Approved
0.7699	Intermediate Similarity	NPD5285	Approved
0.7699	Intermediate Similarity	NPD5286	Approved
0.7699	Intermediate Similarity	NPD7640	Approved
0.7699	Intermediate Similarity	NPD4696	Approved
0.7698	Intermediate Similarity	NPD6336	Discontinued
0.7661	Intermediate Similarity	NPD6016	Approved
0.7661	Intermediate Similarity	NPD6015	Approved
0.7661	Intermediate Similarity	NPD8033	Approved
0.7658	Intermediate Similarity	NPD5695	Phase 3
0.76	Intermediate Similarity	NPD5988	Approved
0.7586	Intermediate Similarity	NPD5141	Approved
0.7581	Intermediate Similarity	NPD6059	Approved
0.7565	Intermediate Similarity	NPD5224	Approved
0.7565	Intermediate Similarity	NPD5225	Approved
0.7565	Intermediate Similarity	NPD4633	Approved
0.7565	Intermediate Similarity	NPD5226	Approved
0.7561	Intermediate Similarity	NPD7328	Approved
0.7561	Intermediate Similarity	NPD7327	Approved
0.7542	Intermediate Similarity	NPD6686	Approved
0.7522	Intermediate Similarity	NPD6083	Phase 2
0.7522	Intermediate Similarity	NPD6084	Phase 2
0.7522	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD7101	Approved
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8293	Discontinued
0.75	Intermediate Similarity	NPD5174	Approved
0.7479	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD5223	Approved
0.744	Intermediate Similarity	NPD8294	Approved
0.744	Intermediate Similarity	NPD8377	Approved
0.7419	Intermediate Similarity	NPD6335	Approved
0.7417	Intermediate Similarity	NPD6371	Approved
0.7405	Intermediate Similarity	NPD7260	Phase 2
0.7398	Intermediate Similarity	NPD6274	Approved
0.7391	Intermediate Similarity	NPD4700	Approved
0.7387	Intermediate Similarity	NPD5284	Approved
0.7387	Intermediate Similarity	NPD5281	Approved
0.7387	Intermediate Similarity	NPD6079	Approved
0.7381	Intermediate Similarity	NPD8379	Approved
0.7381	Intermediate Similarity	NPD8335	Approved
0.7381	Intermediate Similarity	NPD8380	Approved
0.7381	Intermediate Similarity	NPD8296	Approved
0.7381	Intermediate Similarity	NPD8378	Approved
0.7339	Intermediate Similarity	NPD6317	Approved
0.7321	Intermediate Similarity	NPD6399	Phase 3
0.7304	Intermediate Similarity	NPD5696	Approved
0.728	Intermediate Similarity	NPD6313	Approved
0.728	Intermediate Similarity	NPD6314	Approved
0.7273	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4729	Approved
0.725	Intermediate Similarity	NPD4730	Approved
0.7248	Intermediate Similarity	NPD7334	Approved
0.7248	Intermediate Similarity	NPD6684	Approved
0.7248	Intermediate Similarity	NPD7521	Approved
0.7248	Intermediate Similarity	NPD7146	Approved
0.7248	Intermediate Similarity	NPD6409	Approved
0.7248	Intermediate Similarity	NPD5330	Approved
0.7232	Intermediate Similarity	NPD5693	Phase 1
0.7207	Intermediate Similarity	NPD5328	Approved
0.7193	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4202	Approved
0.7167	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD4225	Approved
0.7131	Intermediate Similarity	NPD5248	Approved
0.7131	Intermediate Similarity	NPD5250	Approved
0.7131	Intermediate Similarity	NPD5247	Approved
0.7131	Intermediate Similarity	NPD5249	Phase 3
0.7131	Intermediate Similarity	NPD5251	Approved
0.713	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5222	Approved
0.713	Intermediate Similarity	NPD5221	Approved
0.7119	Intermediate Similarity	NPD7632	Discontinued
0.7117	Intermediate Similarity	NPD6903	Approved
0.7109	Intermediate Similarity	NPD6908	Approved
0.7109	Intermediate Similarity	NPD6909	Approved
0.7109	Intermediate Similarity	NPD8513	Phase 3
0.7109	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5128	Approved
0.7105	Intermediate Similarity	NPD7748	Approved
0.7097	Intermediate Similarity	NPD8133	Approved
0.7091	Intermediate Similarity	NPD5690	Phase 2
0.7083	Intermediate Similarity	NPD4767	Approved
0.7083	Intermediate Similarity	NPD4768	Approved
0.708	Intermediate Similarity	NPD5694	Approved
0.708	Intermediate Similarity	NPD6050	Approved
0.7073	Intermediate Similarity	NPD5215	Approved
0.7073	Intermediate Similarity	NPD5217	Approved
0.7073	Intermediate Similarity	NPD5216	Approved
0.7069	Intermediate Similarity	NPD7902	Approved
0.7069	Intermediate Similarity	NPD5173	Approved
0.7059	Intermediate Similarity	NPD4754	Approved
0.7054	Intermediate Similarity	NPD6904	Approved
0.7054	Intermediate Similarity	NPD6673	Approved
0.7054	Intermediate Similarity	NPD6080	Approved
0.7054	Intermediate Similarity	NPD4753	Phase 2
0.7045	Intermediate Similarity	NPD6033	Approved
0.7043	Intermediate Similarity	NPD4629	Approved
0.7043	Intermediate Similarity	NPD5210	Approved
0.7034	Intermediate Similarity	NPD5344	Discontinued
0.7027	Intermediate Similarity	NPD3573	Approved
0.7025	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5778	Approved
0.7018	Intermediate Similarity	NPD5779	Approved
0.7	Intermediate Similarity	NPD1694	Approved
0.7	Intermediate Similarity	NPD8328	Phase 3
0.6992	Remote Similarity	NPD5169	Approved
0.6992	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5135	Approved
0.6991	Remote Similarity	NPD5785	Approved
0.6991	Remote Similarity	NPD5692	Phase 3
0.6991	Remote Similarity	NPD5207	Approved
0.6991	Remote Similarity	NPD6698	Approved
0.6991	Remote Similarity	NPD46	Approved
0.6984	Remote Similarity	NPD6868	Approved
0.6977	Remote Similarity	NPD8517	Approved
0.6977	Remote Similarity	NPD8515	Approved
0.6977	Remote Similarity	NPD8516	Approved
0.6964	Remote Similarity	NPD6672	Approved
0.6964	Remote Similarity	NPD5737	Approved
0.6963	Remote Similarity	NPD6845	Suspended
0.6935	Remote Similarity	NPD5127	Approved
0.693	Remote Similarity	NPD6411	Approved
0.693	Remote Similarity	NPD7515	Phase 2
0.6911	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3666	Approved
0.6909	Remote Similarity	NPD3133	Approved
0.6909	Remote Similarity	NPD3665	Phase 1
0.6903	Remote Similarity	NPD6051	Approved
0.6881	Remote Similarity	NPD6435	Approved
0.6881	Remote Similarity	NPD4221	Approved
0.6881	Remote Similarity	NPD4223	Phase 3
0.6847	Remote Similarity	NPD5329	Approved
0.6838	Remote Similarity	NPD4697	Phase 3
0.6828	Remote Similarity	NPD7236	Approved
0.6814	Remote Similarity	NPD5208	Approved
0.681	Remote Similarity	NPD7900	Approved
0.681	Remote Similarity	NPD6001	Approved
0.681	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6648	Approved
0.68	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6098	Approved
0.6786	Remote Similarity	NPD4694	Approved
0.6786	Remote Similarity	NPD3618	Phase 1
0.6786	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5280	Approved
0.6783	Remote Similarity	NPD8034	Phase 2
0.6783	Remote Similarity	NPD8035	Phase 2

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