NPASS Compound

Structure

NPC156797 OpenBabel07101719252D 35 39 0 0 1 0 0 0 0 0999 V2000 -6.4325 -6.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -4.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -3.4135 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 -4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.1910 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 1.7321 0.0000 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -4.9190 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 -7.7707 -4.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1235 -5.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -3.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7926 -4.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 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 -4.8363 -3.9680 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 0.8660 -1.5000 0.0000 C 0 0 0 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 -6.4836 -3.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 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 -0.8660 1.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -8.4399 -3.8486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1527 -2.6896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 -3.2248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 8 2 0 0 0 0 7 23 1 0 0 0 0 8 24 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 26 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 22 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 6 0 0 0 15 18 1 0 0 0 0 16 12 1 6 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 1 0 0 0 19 26 1 1 0 0 0 20 27 1 1 0 0 0 21 15 1 1 0 0 0 21 35 1 0 0 0 0 22 28 1 6 0 0 0 22 29 1 0 0 0 0 23 27 1 0 0 0 0 23 31 2 0 0 0 0 24 28 1 1 0 0 0 24 32 1 0 0 0 0 25 33 2 0 0 0 0 25 35 1 0 0 0 0 26 3 1 1 0 0 0 27 28 1 1 0 0 0 28 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.24
Volume:	507.468
LogP:	3.876
LogD:	3.871
LogS:	-4.636
# Rotatable Bonds:	3
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.443
Synthetic Accessibility Score:	5.294
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.008
MDCK Permeability:	1.7988990293815732e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.79
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.38

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.956
Plasma Protein Binding (PPB):	85.40132904052734%
Volume Distribution (VD):	0.632
Pgp-substrate:	4.732893943786621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.579
CYP2C19-inhibitor:	0.215
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.122
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.893
CYP3A4-substrate:	0.853

ADMET: Excretion

Clearance (CL):	7.354
Half-life (T1/2):	0.875

ADMET: Toxicity

hERG Blockers:	0.153
Human Hepatotoxicity (H-HT):	0.226
Drug-inuced Liver Injury (DILI):	0.553
AMES Toxicity:	0.279
Rat Oral Acute Toxicity:	0.168
Maximum Recommended Daily Dose:	0.703
Skin Sensitization:	0.865
Carcinogencity:	0.602
Eye Corrosion:	0.011
Eye Irritation:	0.075
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC156797

Natural Product ID:	NPC156797
*Common Name:**	6Alpha-Chloro-5Beta-Hydroxywithaferin A
IUPAC Name:	(2R)-2-[(1S)-1-[(4S,5R,6S,8S,9S,10R,13S,14S,17R)-6-chloro-4,5-dihydroxy-10,13-dimethyl-1-oxo-6,7,8,9,11,12,14,15,16,17-decahydro-4H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
Synonyms:
Standard InCHIKey:	YCFROFMCBMCGDC-PNJOURQRSA-N
Standard InCHI:	InChI=1S/C28H39ClO6/c1-14-11-21(35-25(33)17(14)13-30)15(2)18-5-6-19-16-12-22(29)28(34)24(32)8-7-23(31)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-22,24,30,32,34H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,22-,24-,26+,27-,28-/m0/s1
SMILES:	CC1=C(CO)C(=O)O[C@H](C1)[C@@H](C)[C@H]1CC[C@H]2[C@@H]3C[C@@H]([C@@]4([C@H](C=CC(=O)[C@]4(C)[C@H]3CC[C@]12C)O)O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047417
PubChem CID:	70686220
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
NPO20281	Withania aristata	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22705001]
NPO20281	Withania aristata	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	16
Others	1

Activity Type	# Activity
Cell Line	17

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	13400.0	nM	PMID[548919]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	14700.0	nM	PMID[548919]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	12100.0	nM	PMID[548919]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8600.0	nM	PMID[548919]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7500.0	nM	PMID[548919]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1300.0	nM	PMID[548919]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	14800.0	nM	PMID[548919]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	7800.0	nM	PMID[548919]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Ratio IC50	=	2.0	n.a.	PMID[548919]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	13400.0	nM	PMID[548920]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	17500.0	nM	PMID[548920]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	14700.0	nM	PMID[548920]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	16100.0	nM	PMID[548920]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7500.0	nM	PMID[548920]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7900.0	nM	PMID[548920]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	14800.0	nM	PMID[548920]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	7800.0	nM	PMID[548920]

☑ 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 NPC156797 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	244
0.1-0.2	1407
0.2-0.3	4339
0.3-0.4	8950
0.4-0.5	13231
0.5-0.6	7897
0.6-0.7	5599
0.7-0.8	965
0.8-0.85	51
0.85-0.9	12
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC287903
0.8889	High Similarity	NPC147912
0.8889	High Similarity	NPC67259
0.8739	High Similarity	NPC140055
0.8739	High Similarity	NPC167606
0.8739	High Similarity	NPC286528
0.8739	High Similarity	NPC20302
0.8667	High Similarity	NPC50774
0.8667	High Similarity	NPC709
0.8644	High Similarity	NPC122056
0.8615	High Similarity	NPC473233
0.8595	High Similarity	NPC264954
0.8583	High Similarity	NPC470493
0.8583	High Similarity	NPC312824
0.8583	High Similarity	NPC183580
0.8583	High Similarity	NPC470492
0.8525	High Similarity	NPC474370
0.8485	Intermediate Similarity	NPC473396
0.8475	Intermediate Similarity	NPC474315
0.8462	Intermediate Similarity	NPC130447
0.8455	Intermediate Similarity	NPC67569
0.845	Intermediate Similarity	NPC296617
0.8387	Intermediate Similarity	NPC88326
0.8387	Intermediate Similarity	NPC153700
0.8387	Intermediate Similarity	NPC23786
0.8387	Intermediate Similarity	NPC470265
0.8347	Intermediate Similarity	NPC64318
0.8321	Intermediate Similarity	NPC245017
0.832	Intermediate Similarity	NPC469789
0.8293	Intermediate Similarity	NPC473274
0.8293	Intermediate Similarity	NPC473270
0.8291	Intermediate Similarity	NPC91034
0.8279	Intermediate Similarity	NPC470959
0.8279	Intermediate Similarity	NPC476965
0.8279	Intermediate Similarity	NPC243065
0.8254	Intermediate Similarity	NPC470494
0.8254	Intermediate Similarity	NPC8369
0.8254	Intermediate Similarity	NPC8374
0.8254	Intermediate Similarity	NPC3381
0.825	Intermediate Similarity	NPC191620
0.8235	Intermediate Similarity	NPC29133
0.8211	Intermediate Similarity	NPC186525
0.8197	Intermediate Similarity	NPC270929
0.8189	Intermediate Similarity	NPC293112
0.8175	Intermediate Similarity	NPC11895
0.8167	Intermediate Similarity	NPC470961
0.816	Intermediate Similarity	NPC473256
0.816	Intermediate Similarity	NPC470878
0.8125	Intermediate Similarity	NPC478207
0.811	Intermediate Similarity	NPC81736
0.811	Intermediate Similarity	NPC172154
0.8099	Intermediate Similarity	NPC69291
0.8095	Intermediate Similarity	NPC170538
0.8083	Intermediate Similarity	NPC37116
0.808	Intermediate Similarity	NPC476961
0.8065	Intermediate Similarity	NPC329736
0.8016	Intermediate Similarity	NPC46570
0.8	Intermediate Similarity	NPC473593
0.8	Intermediate Similarity	NPC61520
0.8	Intermediate Similarity	NPC475065
0.7983	Intermediate Similarity	NPC329048
0.7983	Intermediate Similarity	NPC330011
0.7983	Intermediate Similarity	NPC473284
0.7967	Intermediate Similarity	NPC284915
0.7953	Intermediate Similarity	NPC107493
0.7953	Intermediate Similarity	NPC269642
0.7951	Intermediate Similarity	NPC236217
0.7937	Intermediate Similarity	NPC476962
0.792	Intermediate Similarity	NPC257457
0.792	Intermediate Similarity	NPC311554
0.7917	Intermediate Similarity	NPC473482
0.7917	Intermediate Similarity	NPC475418
0.7917	Intermediate Similarity	NPC318363
0.7917	Intermediate Similarity	NPC220155
0.7907	Intermediate Similarity	NPC473635
0.7881	Intermediate Similarity	NPC475050
0.7879	Intermediate Similarity	NPC231240
0.7863	Intermediate Similarity	NPC476966
0.7857	Intermediate Similarity	NPC475041
0.7857	Intermediate Similarity	NPC476960
0.784	Intermediate Similarity	NPC471854
0.784	Intermediate Similarity	NPC55296
0.782	Intermediate Similarity	NPC316915
0.7787	Intermediate Similarity	NPC473627
0.7778	Intermediate Similarity	NPC474012
0.7778	Intermediate Similarity	NPC476299
0.7769	Intermediate Similarity	NPC472825
0.7759	Intermediate Similarity	NPC253826
0.7752	Intermediate Similarity	NPC204812
0.775	Intermediate Similarity	NPC266570
0.7742	Intermediate Similarity	NPC25909
0.7731	Intermediate Similarity	NPC329345
0.7731	Intermediate Similarity	NPC475526
0.7731	Intermediate Similarity	NPC112009
0.7731	Intermediate Similarity	NPC72151
0.7731	Intermediate Similarity	NPC473283
0.7727	Intermediate Similarity	NPC231529
0.7724	Intermediate Similarity	NPC470960
0.7717	Intermediate Similarity	NPC230513
0.7717	Intermediate Similarity	NPC475520
0.7712	Intermediate Similarity	NPC282524
0.7705	Intermediate Similarity	NPC5475
0.7705	Intermediate Similarity	NPC472216
0.7705	Intermediate Similarity	NPC173905
0.7705	Intermediate Similarity	NPC284828
0.7698	Intermediate Similarity	NPC239273
0.7692	Intermediate Similarity	NPC478056
0.7692	Intermediate Similarity	NPC32868
0.7692	Intermediate Similarity	NPC241456
0.7692	Intermediate Similarity	NPC316598
0.7686	Intermediate Similarity	NPC301666
0.7686	Intermediate Similarity	NPC475294
0.768	Intermediate Similarity	NPC470953
0.768	Intermediate Similarity	NPC474181
0.7661	Intermediate Similarity	NPC269530
0.7661	Intermediate Similarity	NPC475524
0.7661	Intermediate Similarity	NPC476163
0.7661	Intermediate Similarity	NPC100267
0.7656	Intermediate Similarity	NPC154491
0.7656	Intermediate Similarity	NPC268530
0.7656	Intermediate Similarity	NPC79579
0.7647	Intermediate Similarity	NPC114540
0.7647	Intermediate Similarity	NPC320447
0.7647	Intermediate Similarity	NPC32577
0.7647	Intermediate Similarity	NPC155332
0.7647	Intermediate Similarity	NPC136289
0.7638	Intermediate Similarity	NPC153440
0.7623	Intermediate Similarity	NPC472217
0.7623	Intermediate Similarity	NPC472218
0.7623	Intermediate Similarity	NPC472219
0.7619	Intermediate Similarity	NPC190286
0.7619	Intermediate Similarity	NPC470075
0.7619	Intermediate Similarity	NPC148458
0.7619	Intermediate Similarity	NPC176840
0.7615	Intermediate Similarity	NPC120724
0.7615	Intermediate Similarity	NPC473979
0.7603	Intermediate Similarity	NPC189863
0.7597	Intermediate Similarity	NPC4021
0.7597	Intermediate Similarity	NPC159456
0.7583	Intermediate Similarity	NPC476237
0.7583	Intermediate Similarity	NPC95899
0.7583	Intermediate Similarity	NPC180204
0.7583	Intermediate Similarity	NPC476889
0.7583	Intermediate Similarity	NPC297617
0.7583	Intermediate Similarity	NPC478057
0.7578	Intermediate Similarity	NPC5292
0.7578	Intermediate Similarity	NPC42673
0.7576	Intermediate Similarity	NPC473265
0.7576	Intermediate Similarity	NPC287423
0.7576	Intermediate Similarity	NPC470882
0.7576	Intermediate Similarity	NPC473253
0.7563	Intermediate Similarity	NPC81530
0.7563	Intermediate Similarity	NPC224720
0.7563	Intermediate Similarity	NPC115899
0.7563	Intermediate Similarity	NPC476240
0.7563	Intermediate Similarity	NPC476223
0.7561	Intermediate Similarity	NPC41405
0.7561	Intermediate Similarity	NPC322912
0.7561	Intermediate Similarity	NPC214644
0.7559	Intermediate Similarity	NPC473656
0.7559	Intermediate Similarity	NPC476959
0.7559	Intermediate Similarity	NPC134430
0.7559	Intermediate Similarity	NPC284068
0.7542	Intermediate Similarity	NPC98868
0.7542	Intermediate Similarity	NPC57079
0.7542	Intermediate Similarity	NPC108368
0.7542	Intermediate Similarity	NPC278386
0.7542	Intermediate Similarity	NPC124512
0.7542	Intermediate Similarity	NPC159763
0.7541	Intermediate Similarity	NPC67321
0.7541	Intermediate Similarity	NPC255387
0.7541	Intermediate Similarity	NPC187435
0.7541	Intermediate Similarity	NPC131665
0.7537	Intermediate Similarity	NPC196921
0.7537	Intermediate Similarity	NPC220757
0.7536	Intermediate Similarity	NPC250312
0.7521	Intermediate Similarity	NPC242848
0.752	Intermediate Similarity	NPC90952
0.752	Intermediate Similarity	NPC470063
0.752	Intermediate Similarity	NPC285956
0.752	Intermediate Similarity	NPC277769
0.7519	Intermediate Similarity	NPC251226
0.7519	Intermediate Similarity	NPC245094
0.7519	Intermediate Similarity	NPC474585
0.7519	Intermediate Similarity	NPC473620
0.75	Intermediate Similarity	NPC40918
0.75	Intermediate Similarity	NPC198361
0.75	Intermediate Similarity	NPC475913
0.75	Intermediate Similarity	NPC473720
0.75	Intermediate Similarity	NPC146786
0.75	Intermediate Similarity	NPC16270
0.75	Intermediate Similarity	NPC476890
0.748	Intermediate Similarity	NPC476963
0.748	Intermediate Similarity	NPC306265
0.748	Intermediate Similarity	NPC177064
0.7479	Intermediate Similarity	NPC201406
0.7479	Intermediate Similarity	NPC476274
0.7479	Intermediate Similarity	NPC266955
0.7463	Intermediate Similarity	NPC471407
0.7463	Intermediate Similarity	NPC221414

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 NPC156797 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	1510
0.2-0.3	3682
0.3-0.4	2532
0.4-0.5	770
0.5-0.6	220
0.6-0.7	170
0.7-0.8	59
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8739	High Similarity	NPD7115	Discovery
0.8145	Intermediate Similarity	NPD7101	Approved
0.8145	Intermediate Similarity	NPD7100	Approved
0.8049	Intermediate Similarity	NPD6868	Approved
0.7769	Intermediate Similarity	NPD6336	Discontinued
0.7724	Intermediate Similarity	NPD5216	Approved
0.7724	Intermediate Similarity	NPD5215	Approved
0.7724	Intermediate Similarity	NPD5217	Approved
0.768	Intermediate Similarity	NPD5167	Approved
0.7638	Intermediate Similarity	NPD6335	Approved
0.7623	Intermediate Similarity	NPD5168	Approved
0.7542	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD6313	Approved
0.75	Intermediate Similarity	NPD6314	Approved
0.7442	Intermediate Similarity	NPD4522	Approved
0.7339	Intermediate Similarity	NPD6899	Approved
0.7339	Intermediate Similarity	NPD6881	Approved
0.7328	Intermediate Similarity	NPD5983	Phase 2
0.7323	Intermediate Similarity	NPD4632	Approved
0.7302	Intermediate Similarity	NPD6649	Approved
0.7302	Intermediate Similarity	NPD6650	Approved
0.7258	Intermediate Similarity	NPD5697	Approved
0.7244	Intermediate Similarity	NPD8297	Approved
0.7222	Intermediate Similarity	NPD6883	Approved
0.7222	Intermediate Similarity	NPD7102	Approved
0.7222	Intermediate Similarity	NPD5169	Approved
0.7222	Intermediate Similarity	NPD7290	Approved
0.719	Intermediate Similarity	NPD7639	Approved
0.719	Intermediate Similarity	NPD7640	Approved
0.7177	Intermediate Similarity	NPD7128	Approved
0.7177	Intermediate Similarity	NPD6675	Approved
0.7177	Intermediate Similarity	NPD6402	Approved
0.7177	Intermediate Similarity	NPD5739	Approved
0.7165	Intermediate Similarity	NPD6847	Approved
0.7165	Intermediate Similarity	NPD8130	Phase 1
0.7165	Intermediate Similarity	NPD6869	Approved
0.7165	Intermediate Similarity	NPD5127	Approved
0.7165	Intermediate Similarity	NPD6617	Approved
0.7153	Intermediate Similarity	NPD5956	Approved
0.7143	Intermediate Similarity	NPD6012	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD6014	Approved
0.7143	Intermediate Similarity	NPD6013	Approved
0.7121	Intermediate Similarity	NPD6319	Approved
0.7119	Intermediate Similarity	NPD6399	Phase 3
0.7109	Intermediate Similarity	NPD6882	Approved
0.7107	Intermediate Similarity	NPD7638	Approved
0.7073	Intermediate Similarity	NPD5211	Phase 2
0.7063	Intermediate Similarity	NPD7320	Approved
0.7063	Intermediate Similarity	NPD6011	Approved
0.7034	Intermediate Similarity	NPD6079	Approved
0.7025	Intermediate Similarity	NPD6084	Phase 2
0.7025	Intermediate Similarity	NPD6083	Phase 2
0.7023	Intermediate Similarity	NPD6009	Approved
0.7007	Intermediate Similarity	NPD6033	Approved
0.6984	Remote Similarity	NPD6614	Approved
0.6984	Remote Similarity	NPD5701	Approved
0.696	Remote Similarity	NPD5141	Approved
0.6957	Remote Similarity	NPD7319	Approved
0.6953	Remote Similarity	NPD4634	Approved
0.6949	Remote Similarity	NPD5785	Approved
0.6929	Remote Similarity	NPD5128	Approved
0.6917	Remote Similarity	NPD7748	Approved
0.6912	Remote Similarity	NPD7492	Approved
0.6911	Remote Similarity	NPD5286	Approved
0.6911	Remote Similarity	NPD5285	Approved
0.6911	Remote Similarity	NPD4696	Approved
0.6897	Remote Similarity	NPD3618	Phase 1
0.6891	Remote Similarity	NPD7515	Phase 2
0.6885	Remote Similarity	NPD7902	Approved
0.6884	Remote Similarity	NPD7736	Approved
0.6866	Remote Similarity	NPD6054	Approved
0.6864	Remote Similarity	NPD5328	Approved
0.6861	Remote Similarity	NPD6616	Approved
0.6861	Remote Similarity	NPD7507	Approved
0.6829	Remote Similarity	NPD5696	Approved
0.6815	Remote Similarity	NPD7503	Approved
0.6812	Remote Similarity	NPD7078	Approved
0.6803	Remote Similarity	NPD5222	Approved
0.6803	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5221	Approved
0.68	Remote Similarity	NPD5091	Approved
0.68	Remote Similarity	NPD5225	Approved
0.68	Remote Similarity	NPD5226	Approved
0.68	Remote Similarity	NPD5224	Approved
0.68	Remote Similarity	NPD4633	Approved
0.6769	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6370	Approved
0.6752	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5173	Approved
0.6748	Remote Similarity	NPD4755	Approved
0.6746	Remote Similarity	NPD5175	Approved
0.6746	Remote Similarity	NPD5174	Approved
0.6744	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4786	Approved
0.6721	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5210	Approved
0.6721	Remote Similarity	NPD5695	Phase 3
0.6721	Remote Similarity	NPD4629	Approved
0.672	Remote Similarity	NPD5223	Approved
0.6694	Remote Similarity	NPD4202	Approved
0.6692	Remote Similarity	NPD6274	Approved
0.6692	Remote Similarity	NPD6371	Approved
0.6691	Remote Similarity	NPD6015	Approved
0.6691	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6642	Remote Similarity	NPD6317	Approved
0.6642	Remote Similarity	NPD5988	Approved
0.6641	Remote Similarity	NPD6008	Approved
0.664	Remote Similarity	NPD4700	Approved
0.6639	Remote Similarity	NPD7900	Approved
0.6639	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5737	Approved
0.6639	Remote Similarity	NPD6672	Approved
0.6639	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6059	Approved
0.6612	Remote Similarity	NPD8034	Phase 2
0.6612	Remote Similarity	NPD8035	Phase 2
0.6612	Remote Similarity	NPD7637	Suspended
0.6612	Remote Similarity	NPD5693	Phase 1
0.661	Remote Similarity	NPD7334	Approved
0.661	Remote Similarity	NPD7146	Approved
0.661	Remote Similarity	NPD6684	Approved
0.661	Remote Similarity	NPD6409	Approved
0.661	Remote Similarity	NPD5330	Approved
0.661	Remote Similarity	NPD7521	Approved
0.6594	Remote Similarity	NPD7604	Phase 2
0.6593	Remote Similarity	NPD7328	Approved
0.6593	Remote Similarity	NPD7327	Approved
0.6591	Remote Similarity	NPD6053	Discontinued
0.6589	Remote Similarity	NPD6412	Phase 2
0.6583	Remote Similarity	NPD4753	Phase 2
0.6571	Remote Similarity	NPD8293	Discontinued
0.6569	Remote Similarity	NPD8513	Phase 3
0.6569	Remote Similarity	NPD8033	Approved
0.6569	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD3573	Approved
0.6552	Remote Similarity	NPD3667	Approved
0.6544	Remote Similarity	NPD7516	Approved
0.6538	Remote Similarity	NPD4729	Approved
0.6538	Remote Similarity	NPD4730	Approved
0.6525	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5363	Approved
0.65	Remote Similarity	NPD6903	Approved
0.6496	Remote Similarity	NPD8294	Approved
0.6496	Remote Similarity	NPD8377	Approved
0.6475	Remote Similarity	NPD5281	Approved
0.6475	Remote Similarity	NPD6411	Approved
0.6475	Remote Similarity	NPD8328	Phase 3
0.6475	Remote Similarity	NPD5284	Approved
0.6452	Remote Similarity	NPD5654	Approved
0.6452	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD8378	Approved
0.6449	Remote Similarity	NPD8515	Approved
0.6449	Remote Similarity	NPD6908	Approved
0.6449	Remote Similarity	NPD6909	Approved
0.6449	Remote Similarity	NPD8380	Approved
0.6449	Remote Similarity	NPD8379	Approved
0.6449	Remote Similarity	NPD8296	Approved
0.6449	Remote Similarity	NPD8516	Approved
0.6449	Remote Similarity	NPD8335	Approved
0.6449	Remote Similarity	NPD8517	Approved
0.6446	Remote Similarity	NPD6904	Approved
0.6446	Remote Similarity	NPD6673	Approved
0.6446	Remote Similarity	NPD6080	Approved
0.6441	Remote Similarity	NPD3133	Approved
0.6441	Remote Similarity	NPD3665	Phase 1
0.6441	Remote Similarity	NPD3666	Approved
0.6439	Remote Similarity	NPD5247	Approved
0.6439	Remote Similarity	NPD5251	Approved
0.6439	Remote Similarity	NPD5250	Approved
0.6439	Remote Similarity	NPD5248	Approved
0.6439	Remote Similarity	NPD5249	Phase 3
0.6423	Remote Similarity	NPD5779	Approved
0.6423	Remote Similarity	NPD5778	Approved
0.641	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD4767	Approved
0.6385	Remote Similarity	NPD4768	Approved
0.6371	Remote Similarity	NPD6001	Approved
0.6357	Remote Similarity	NPD4754	Approved
0.6349	Remote Similarity	NPD5959	Approved
0.6336	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5344	Discontinued
0.6316	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5135	Approved
0.6311	Remote Similarity	NPD6101	Approved
0.6311	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6051	Approved
0.6296	Remote Similarity	NPD8133	Approved
0.6271	Remote Similarity	NPD4270	Approved
0.6271	Remote Similarity	NPD4269	Approved
0.6271	Remote Similarity	NPD4221	Approved
0.6271	Remote Similarity	NPD4223	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