NPASS Compound

Structure

CID120994 OpenBabel06191715472D 39 44 0 0 1 0 0 0 0 0999 V2000 10.2549 -5.1241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9986 -4.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0812 -3.9596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5304 -2.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7809 -2.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7810 -1.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3807 -2.9451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2310 -3.4361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5932 -4.7706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2314 -0.4912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8311 -1.4725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8468 -7.0428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3220 -5.4270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9315 -4.4172 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2312 -1.4730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1179 -6.3864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9316 -3.4363 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0815 -1.9640 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3808 -1.9638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6603 -5.0736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8312 -0.4907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6808 -1.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3811 -0.0001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6810 0.0001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1851 -6.6894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0814 -2.9453 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5306 -1.4728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5307 -0.4909 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.6427 -8.0022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6806 -2.9636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6812 1.0001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9810 -7.6488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9814 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9814 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9814 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4562 -6.0330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5309 0.4910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9814 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 26 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 23 1 0 0 0 0 11 21 1 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 29 1 0 0 0 0 13 16 2 0 0 0 0 14 2 1 1 0 0 0 14 17 1 0 0 0 0 15 10 1 1 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 25 1 0 0 0 0 17 26 1 6 0 0 0 18 26 1 6 0 0 0 19 27 1 6 0 0 0 20 14 1 1 0 0 0 20 36 1 0 0 0 0 21 24 1 0 0 0 0 21 38 1 6 0 0 0 22 27 1 0 0 0 0 22 30 2 0 0 0 0 23 28 1 6 0 0 0 23 37 1 0 0 0 0 24 28 1 6 0 0 0 24 31 1 0 0 0 0 25 32 2 0 0 0 0 25 36 1 0 0 0 0 26 3 1 6 0 0 0 27 28 1 6 0 0 0 28 37 1 6 0 0 0 33 39 1 0 0 0 0 34 39 2 0 0 0 0 35 39 2 0 0 0 0 38 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.23
Volume:	540.007
LogP:	0.909
LogD:	1.718
LogS:	-2.204
# Rotatable Bonds:	5
TPSA:	159.96
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.255
Synthetic Accessibility Score:	5.937
Fsp3:	0.857
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:	-5.355
MDCK Permeability:	1.6515898096258752e-05
Pgp-inhibitor:	0.274
Pgp-substrate:	0.79
Human Intestinal Absorption (HIA):	0.888
20% Bioavailability (F20%):	0.947
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.552
Plasma Protein Binding (PPB):	78.72403717041016%
Volume Distribution (VD):	0.806
Pgp-substrate:	10.16319751739502%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.241
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.771
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.086
CYP3A4-substrate:	0.271

ADMET: Excretion

Clearance (CL):	8.065
Half-life (T1/2):	0.627

ADMET: Toxicity

hERG Blockers:	0.352
Human Hepatotoxicity (H-HT):	0.861
Drug-inuced Liver Injury (DILI):	0.235
AMES Toxicity:	0.124
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.921
Carcinogencity:	0.868
Eye Corrosion:	0.391
Eye Irritation:	0.079
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC120994

Natural Product ID:	NPC120994
*Common Name:**	DVTZXBWRHRFDEE-WQWZRYHASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DVTZXBWRHRFDEE-WQWZRYHASA-N
Standard InCHI:	InChI=1S/C28H40O10S/c1-13-9-20(36-25(32)16(13)12-29)14(2)17-5-6-18-15-10-23-28(37-23)24(31)21(38-39(33,34)35)11-22(30)27(28,4)19(15)7-8-26(17,18)3/h14-15,17-21,23-24,29,31H,5-12H2,1-4H3,(H,33,34,35)/t14-,15-,17+,18-,19-,20+,21-,23+,24-,26+,27-,28-/m0/s1
SMILES:	OCC1=C(C)C[C@@H](OC1=O)[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H]2[C@]3([C@]1(C)C(=O)C[C@@H]([C@@H]3O)OS(=O)(=O)O)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469945
PubChem CID:	44581669
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	11
Others	1

Activity Type	# Activity
Cell Line	4
Individual Protein	1
NON-MOLECULAR	4
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	=	180.0	nM	PMID[523978]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	5100.0	nM	PMID[523978]
NPT4377	Individual Protein	Heat shock 70 kDa protein 6	Homo sapiens	FC	=	0.0	n.a.	PMID[523979]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	21700.0	nM	PMID[523980]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	17900.0	nM	PMID[523980]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	480.0	nM	PMID[523978]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	270.0	nM	PMID[523978]
NPT27	Others	Unspecified		IC50	=	1400.0	nM	PMID[523978]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5250.0	nM	PMID[523979]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14800.0	nM	PMID[523980]
NPT2	Others	Unspecified		IC50	=	2200.0	nM	PMID[523980]
NPT27	Others	Unspecified		IC50	=	21000.0	nM	PMID[523980]

☑ 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 NPC120994 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	314
0.1-0.2	1840
0.2-0.3	5068
0.3-0.4	8107
0.4-0.5	12282
0.5-0.6	7299
0.6-0.7	5724
0.7-0.8	1865
0.8-0.85	151
0.85-0.9	32
0.9-0.95	8
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC203702
0.9652	High Similarity	NPC4021
0.9652	High Similarity	NPC159456
0.9565	High Similarity	NPC154491
0.9565	High Similarity	NPC251226
0.9565	High Similarity	NPC268530
0.9304	High Similarity	NPC55296
0.9244	High Similarity	NPC469790
0.9145	High Similarity	NPC230513
0.9145	High Similarity	NPC42673
0.913	High Similarity	NPC284915
0.9008	High Similarity	NPC293112
0.8852	High Similarity	NPC473635
0.8843	High Similarity	NPC11895
0.8843	High Similarity	NPC469789
0.877	High Similarity	NPC81736
0.877	High Similarity	NPC172154
0.876	High Similarity	NPC170538
0.876	High Similarity	NPC23786
0.876	High Similarity	NPC470265
0.876	High Similarity	NPC269642
0.8678	High Similarity	NPC67569
0.8632	High Similarity	NPC476163
0.8618	High Similarity	NPC8369
0.8512	High Similarity	NPC475041
0.85	High Similarity	NPC58662
0.8492	Intermediate Similarity	NPC231529
0.843	Intermediate Similarity	NPC113448
0.843	Intermediate Similarity	NPC709
0.843	Intermediate Similarity	NPC50774
0.839	Intermediate Similarity	NPC474846
0.839	Intermediate Similarity	NPC469655
0.839	Intermediate Similarity	NPC469656
0.8362	Intermediate Similarity	NPC473165
0.8347	Intermediate Similarity	NPC167606
0.8347	Intermediate Similarity	NPC140055
0.8347	Intermediate Similarity	NPC286528
0.8347	Intermediate Similarity	NPC20302
0.8347	Intermediate Similarity	NPC469684
0.832	Intermediate Similarity	NPC8374
0.8293	Intermediate Similarity	NPC474370
0.8279	Intermediate Similarity	NPC108581
0.8279	Intermediate Similarity	NPC478206
0.8279	Intermediate Similarity	NPC478205
0.8276	Intermediate Similarity	NPC470587
0.824	Intermediate Similarity	NPC67251
0.8226	Intermediate Similarity	NPC470779
0.8226	Intermediate Similarity	NPC46570
0.8217	Intermediate Similarity	NPC231240
0.8211	Intermediate Similarity	NPC264954
0.8211	Intermediate Similarity	NPC475520
0.8205	Intermediate Similarity	NPC9457
0.8205	Intermediate Similarity	NPC471783
0.8203	Intermediate Similarity	NPC473593
0.8197	Intermediate Similarity	NPC470492
0.8197	Intermediate Similarity	NPC478204
0.8197	Intermediate Similarity	NPC470493
0.8197	Intermediate Similarity	NPC13713
0.8197	Intermediate Similarity	NPC53396
0.8197	Intermediate Similarity	NPC183580
0.8197	Intermediate Similarity	NPC312824
0.8197	Intermediate Similarity	NPC98249
0.8182	Intermediate Similarity	NPC67259
0.8182	Intermediate Similarity	NPC147912
0.8175	Intermediate Similarity	NPC476729
0.8167	Intermediate Similarity	NPC269530
0.8167	Intermediate Similarity	NPC476964
0.8167	Intermediate Similarity	NPC42658
0.816	Intermediate Similarity	NPC88326
0.816	Intermediate Similarity	NPC153700
0.816	Intermediate Similarity	NPC107493
0.8154	Intermediate Similarity	NPC316915
0.8145	Intermediate Similarity	NPC476961
0.8136	Intermediate Similarity	NPC469916
0.8136	Intermediate Similarity	NPC472439
0.8136	Intermediate Similarity	NPC273155
0.813	Intermediate Similarity	NPC284707
0.813	Intermediate Similarity	NPC251310
0.813	Intermediate Similarity	NPC240509
0.8125	Intermediate Similarity	NPC473620
0.8115	Intermediate Similarity	NPC270929
0.8099	Intermediate Similarity	NPC25909
0.8099	Intermediate Similarity	NPC122056
0.8099	Intermediate Similarity	NPC317210
0.8099	Intermediate Similarity	NPC250109
0.8099	Intermediate Similarity	NPC962
0.8095	Intermediate Similarity	NPC265557
0.8095	Intermediate Similarity	NPC91693
0.8095	Intermediate Similarity	NPC18945
0.8095	Intermediate Similarity	NPC105926
0.808	Intermediate Similarity	NPC129434
0.8065	Intermediate Similarity	NPC77689
0.8065	Intermediate Similarity	NPC61520
0.8065	Intermediate Similarity	NPC476960
0.8065	Intermediate Similarity	NPC473839
0.8065	Intermediate Similarity	NPC211093
0.8065	Intermediate Similarity	NPC473636
0.8062	Intermediate Similarity	NPC476966
0.8062	Intermediate Similarity	NPC470880
0.8051	Intermediate Similarity	NPC180744
0.8051	Intermediate Similarity	NPC112780
0.8051	Intermediate Similarity	NPC166993
0.8049	Intermediate Similarity	NPC475809
0.8049	Intermediate Similarity	NPC134430
0.8047	Intermediate Similarity	NPC469757
0.8047	Intermediate Similarity	NPC146456
0.8047	Intermediate Similarity	NPC287423
0.8047	Intermediate Similarity	NPC298841
0.8047	Intermediate Similarity	NPC470882
0.8047	Intermediate Similarity	NPC471357
0.8047	Intermediate Similarity	NPC117702
0.8047	Intermediate Similarity	NPC473253
0.8047	Intermediate Similarity	NPC42399
0.8034	Intermediate Similarity	NPC65523
0.8031	Intermediate Similarity	NPC3381
0.8031	Intermediate Similarity	NPC470922
0.8031	Intermediate Similarity	NPC24651
0.8031	Intermediate Similarity	NPC318135
0.8017	Intermediate Similarity	NPC472002
0.8016	Intermediate Similarity	NPC312833
0.8016	Intermediate Similarity	NPC222688
0.8	Intermediate Similarity	NPC173347
0.7984	Intermediate Similarity	NPC473720
0.7984	Intermediate Similarity	NPC186525
0.7984	Intermediate Similarity	NPC329736
0.7984	Intermediate Similarity	NPC311534
0.7967	Intermediate Similarity	NPC266728
0.7967	Intermediate Similarity	NPC173686
0.7967	Intermediate Similarity	NPC16081
0.7967	Intermediate Similarity	NPC470075
0.7967	Intermediate Similarity	NPC49492
0.7966	Intermediate Similarity	NPC470979
0.7966	Intermediate Similarity	NPC200957
0.7966	Intermediate Similarity	NPC470975
0.7966	Intermediate Similarity	NPC138908
0.7966	Intermediate Similarity	NPC103088
0.7953	Intermediate Similarity	NPC471392
0.7953	Intermediate Similarity	NPC473979
0.7953	Intermediate Similarity	NPC472399
0.7953	Intermediate Similarity	NPC204812
0.7953	Intermediate Similarity	NPC120724
0.7951	Intermediate Similarity	NPC478212
0.7951	Intermediate Similarity	NPC477126
0.7951	Intermediate Similarity	NPC475966
0.7949	Intermediate Similarity	NPC159533
0.7937	Intermediate Similarity	NPC310511
0.7937	Intermediate Similarity	NPC477046
0.7937	Intermediate Similarity	NPC102822
0.7934	Intermediate Similarity	NPC94650
0.7923	Intermediate Similarity	NPC469753
0.7923	Intermediate Similarity	NPC197707
0.7923	Intermediate Similarity	NPC219085
0.7923	Intermediate Similarity	NPC6108
0.7923	Intermediate Similarity	NPC469752
0.7923	Intermediate Similarity	NPC471360
0.7923	Intermediate Similarity	NPC70542
0.7923	Intermediate Similarity	NPC471352
0.7923	Intermediate Similarity	NPC86159
0.7923	Intermediate Similarity	NPC469754
0.7923	Intermediate Similarity	NPC471359
0.7923	Intermediate Similarity	NPC469751
0.7923	Intermediate Similarity	NPC251866
0.7923	Intermediate Similarity	NPC471358
0.7923	Intermediate Similarity	NPC221414
0.7923	Intermediate Similarity	NPC469755
0.7923	Intermediate Similarity	NPC471361
0.7923	Intermediate Similarity	NPC180079
0.7923	Intermediate Similarity	NPC284406
0.7923	Intermediate Similarity	NPC89514
0.7923	Intermediate Similarity	NPC17896
0.7923	Intermediate Similarity	NPC10823
0.7923	Intermediate Similarity	NPC9499
0.792	Intermediate Similarity	NPC473203
0.792	Intermediate Similarity	NPC5292
0.792	Intermediate Similarity	NPC473274
0.792	Intermediate Similarity	NPC232258
0.792	Intermediate Similarity	NPC472667
0.7917	Intermediate Similarity	NPC299590
0.7917	Intermediate Similarity	NPC273433
0.7907	Intermediate Similarity	NPC473265
0.7903	Intermediate Similarity	NPC474654
0.7903	Intermediate Similarity	NPC243065
0.7903	Intermediate Similarity	NPC470959
0.7903	Intermediate Similarity	NPC470778
0.7903	Intermediate Similarity	NPC97908
0.7903	Intermediate Similarity	NPC146432
0.7903	Intermediate Similarity	NPC470854
0.7903	Intermediate Similarity	NPC122033
0.7903	Intermediate Similarity	NPC470775
0.7903	Intermediate Similarity	NPC287343
0.7903	Intermediate Similarity	NPC476965
0.7903	Intermediate Similarity	NPC473590
0.7903	Intermediate Similarity	NPC176513
0.7903	Intermediate Similarity	NPC473968
0.7899	Intermediate Similarity	NPC67321
0.7899	Intermediate Similarity	NPC187435
0.7891	Intermediate Similarity	NPC233041
0.7891	Intermediate Similarity	NPC32868
0.7891	Intermediate Similarity	NPC473709
0.7891	Intermediate Similarity	NPC470494

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 NPC120994 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	2063
0.2-0.3	3812
0.3-0.4	1945
0.4-0.5	595
0.5-0.6	281
0.6-0.7	156
0.7-0.8	21
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8347	Intermediate Similarity	NPD7115	Discovery
0.7923	Intermediate Similarity	NPD7319	Approved
0.7917	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7507	Approved
0.7603	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6319	Approved
0.7395	Intermediate Similarity	NPD7640	Approved
0.7395	Intermediate Similarity	NPD7639	Approved
0.7364	Intermediate Similarity	NPD7516	Approved
0.7311	Intermediate Similarity	NPD7638	Approved
0.7287	Intermediate Similarity	NPD7327	Approved
0.7287	Intermediate Similarity	NPD7328	Approved
0.7273	Intermediate Similarity	NPD7632	Discontinued
0.7236	Intermediate Similarity	NPD6008	Approved
0.7209	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6373	Approved
0.72	Intermediate Similarity	NPD6372	Approved
0.7185	Intermediate Similarity	NPD7736	Approved
0.7167	Intermediate Similarity	NPD4225	Approved
0.7165	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD8328	Phase 3
0.7121	Intermediate Similarity	NPD8378	Approved
0.7121	Intermediate Similarity	NPD8033	Approved
0.7121	Intermediate Similarity	NPD8335	Approved
0.7121	Intermediate Similarity	NPD8296	Approved
0.7121	Intermediate Similarity	NPD8380	Approved
0.7121	Intermediate Similarity	NPD8379	Approved
0.7109	Intermediate Similarity	NPD4632	Approved
0.7097	Intermediate Similarity	NPD7128	Approved
0.7097	Intermediate Similarity	NPD6402	Approved
0.7097	Intermediate Similarity	NPD5739	Approved
0.7097	Intermediate Similarity	NPD6675	Approved
0.709	Intermediate Similarity	NPD7492	Approved
0.7087	Intermediate Similarity	NPD6650	Approved
0.7087	Intermediate Similarity	NPD6649	Approved
0.7063	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD8294	Approved
0.7045	Intermediate Similarity	NPD6059	Approved
0.7045	Intermediate Similarity	NPD8377	Approved
0.7045	Intermediate Similarity	NPD6054	Approved
0.7037	Intermediate Similarity	NPD6616	Approved
0.7008	Intermediate Similarity	NPD6371	Approved
0.6992	Remote Similarity	NPD6921	Approved
0.6992	Remote Similarity	NPD8513	Phase 3
0.6985	Remote Similarity	NPD8293	Discontinued
0.6985	Remote Similarity	NPD7078	Approved
0.6984	Remote Similarity	NPD6899	Approved
0.6984	Remote Similarity	NPD6881	Approved
0.6984	Remote Similarity	NPD7320	Approved
0.6984	Remote Similarity	NPD6686	Approved
0.6977	Remote Similarity	NPD8133	Approved
0.694	Remote Similarity	NPD6370	Approved
0.6911	Remote Similarity	NPD5344	Discontinued
0.6905	Remote Similarity	NPD5697	Approved
0.6905	Remote Similarity	NPD5701	Approved
0.6899	Remote Similarity	NPD6053	Discontinued
0.6899	Remote Similarity	NPD6882	Approved
0.6889	Remote Similarity	NPD7604	Phase 2
0.6875	Remote Similarity	NPD6883	Approved
0.6875	Remote Similarity	NPD7102	Approved
0.6875	Remote Similarity	NPD7290	Approved
0.6875	Remote Similarity	NPD4634	Approved
0.6866	Remote Similarity	NPD8517	Approved
0.6866	Remote Similarity	NPD7503	Approved
0.6866	Remote Similarity	NPD8516	Approved
0.6866	Remote Similarity	NPD8515	Approved
0.6866	Remote Similarity	NPD6016	Approved
0.6866	Remote Similarity	NPD6015	Approved
0.6822	Remote Similarity	NPD6617	Approved
0.6822	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD8130	Phase 1
0.6822	Remote Similarity	NPD6869	Approved
0.6822	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD6009	Approved
0.6815	Remote Similarity	NPD5988	Approved
0.6797	Remote Similarity	NPD6014	Approved
0.6797	Remote Similarity	NPD6012	Approved
0.6797	Remote Similarity	NPD6013	Approved
0.6772	Remote Similarity	NPD6412	Phase 2
0.675	Remote Similarity	NPD6399	Phase 3
0.6741	Remote Similarity	NPD5983	Phase 2
0.6723	Remote Similarity	NPD6698	Approved
0.6723	Remote Similarity	NPD46	Approved
0.672	Remote Similarity	NPD5211	Phase 2
0.6719	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6639	Remote Similarity	NPD5328	Approved
0.6614	Remote Similarity	NPD5141	Approved
0.6571	Remote Similarity	NPD6033	Approved
0.656	Remote Similarity	NPD4696	Approved
0.656	Remote Similarity	NPD4700	Approved
0.656	Remote Similarity	NPD5285	Approved
0.656	Remote Similarity	NPD5286	Approved
0.656	Remote Similarity	NPD6648	Approved
0.6557	Remote Similarity	NPD7748	Approved
0.6532	Remote Similarity	NPD6083	Phase 2
0.6532	Remote Similarity	NPD6084	Phase 2
0.6529	Remote Similarity	NPD6079	Approved
0.6529	Remote Similarity	NPD7515	Phase 2
0.6529	Remote Similarity	NPD7637	Suspended
0.6512	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD1700	Approved
0.65	Remote Similarity	NPD8074	Phase 3
0.6493	Remote Similarity	NPD6274	Approved
0.6471	Remote Similarity	NPD7101	Approved
0.6471	Remote Similarity	NPD7100	Approved
0.6457	Remote Similarity	NPD5225	Approved
0.6457	Remote Similarity	NPD5226	Approved
0.6457	Remote Similarity	NPD4633	Approved
0.6457	Remote Similarity	NPD5224	Approved
0.6452	Remote Similarity	NPD4697	Phase 3
0.6444	Remote Similarity	NPD6317	Approved
0.6441	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD4768	Approved
0.6434	Remote Similarity	NPD7260	Phase 2
0.6434	Remote Similarity	NPD4767	Approved
0.6423	Remote Similarity	NPD7900	Approved
0.6423	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5175	Approved
0.6406	Remote Similarity	NPD5174	Approved
0.6406	Remote Similarity	NPD4754	Approved
0.6397	Remote Similarity	NPD6335	Approved
0.6393	Remote Similarity	NPD7983	Approved
0.6389	Remote Similarity	NPD6845	Suspended
0.6387	Remote Similarity	NPD3618	Phase 1
0.6378	Remote Similarity	NPD5223	Approved
0.6378	Remote Similarity	NPD4159	Approved
0.6377	Remote Similarity	NPD6908	Approved
0.6377	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6909	Approved
0.6371	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5696	Approved
0.6341	Remote Similarity	NPD5778	Approved
0.6341	Remote Similarity	NPD5779	Approved
0.6341	Remote Similarity	NPD4202	Approved
0.6336	Remote Similarity	NPD4730	Approved
0.6336	Remote Similarity	NPD4729	Approved
0.6333	Remote Similarity	NPD7524	Approved
0.632	Remote Similarity	NPD5221	Approved
0.632	Remote Similarity	NPD5222	Approved
0.632	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5785	Approved
0.6281	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6314	Approved
0.6277	Remote Similarity	NPD6313	Approved
0.627	Remote Similarity	NPD5173	Approved
0.6261	Remote Similarity	NPD6697	Approved
0.6261	Remote Similarity	NPD6118	Approved
0.6261	Remote Similarity	NPD6114	Approved
0.6261	Remote Similarity	NPD6115	Approved
0.625	Remote Similarity	NPD6868	Approved
0.625	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD5248	Approved
0.6241	Remote Similarity	NPD5251	Approved
0.6241	Remote Similarity	NPD5250	Approved
0.6241	Remote Similarity	NPD5247	Approved
0.6241	Remote Similarity	NPD5249	Phase 3
0.624	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.624	Remote Similarity	NPD5695	Phase 3
0.6218	Remote Similarity	NPD4786	Approved
0.6218	Remote Similarity	NPD3668	Phase 3
0.6212	Remote Similarity	NPD5128	Approved
0.6179	Remote Similarity	NPD7838	Discovery
0.6174	Remote Similarity	NPD6116	Phase 1
0.617	Remote Similarity	NPD6067	Discontinued
0.6148	Remote Similarity	NPD5737	Approved
0.6148	Remote Similarity	NPD6672	Approved
0.6129	Remote Similarity	NPD5693	Phase 1
0.6129	Remote Similarity	NPD6411	Approved
0.6119	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD5135	Approved
0.6116	Remote Similarity	NPD6409	Approved
0.6116	Remote Similarity	NPD7146	Approved
0.6116	Remote Similarity	NPD7334	Approved
0.6116	Remote Similarity	NPD6684	Approved
0.6116	Remote Similarity	NPD5330	Approved
0.6116	Remote Similarity	NPD7521	Approved
0.6098	Remote Similarity	NPD4753	Phase 2
0.6095	Remote Similarity	NPD7799	Discontinued
0.609	Remote Similarity	NPD7236	Approved
0.6087	Remote Similarity	NPD6117	Approved
0.6083	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD5215	Approved
0.6074	Remote Similarity	NPD5217	Approved
0.6074	Remote Similarity	NPD5216	Approved
0.6066	Remote Similarity	NPD3573	Approved
0.6065	Remote Similarity	NPD7625	Phase 1
0.6056	Remote Similarity	NPD7642	Approved
0.605	Remote Similarity	NPD3667	Approved
0.6033	Remote Similarity	NPD1694	Approved
0.6032	Remote Similarity	NPD6001	Approved
0.6017	Remote Similarity	NPD7525	Registered

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