NPASS Compound

Structure

NPC243065 OpenBabel07101719132D 34 39 0 0 1 0 0 0 0 0999 V2000 -7.1527 3.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 5.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 4.2248 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 -7.7707 5.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 4.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 4.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7926 5.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 3.8090 0.0000 C 0 0 2 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 -0.8660 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8363 4.9680 0.0000 C 0 0 2 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1235 6.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0798 6.5428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4325 7.0780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 5.9190 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 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 22 1 0 0 0 0 8 23 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 24 1 0 0 0 0 13 17 1 0 0 0 0 13 29 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 12 1 1 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 6 0 0 0 19 26 1 6 0 0 0 20 27 1 6 0 0 0 21 15 1 1 0 0 0 21 33 1 0 0 0 0 22 27 1 0 0 0 0 22 30 2 0 0 0 0 23 31 2 0 0 0 0 24 28 1 6 0 0 0 24 34 1 0 0 0 0 25 32 2 0 0 0 0 25 33 1 0 0 0 0 26 3 1 6 0 0 0 27 28 1 6 0 0 0 28 23 1 1 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.25
Volume:	481.064
LogP:	3.548
LogD:	3.473
LogS:	-4.635
# Rotatable Bonds:	3
TPSA:	93.2
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.503
Synthetic Accessibility Score:	5.716
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.191
MDCK Permeability:	1.6882102499948815e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.143
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.645

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.236
Plasma Protein Binding (PPB):	83.83707427978516%
Volume Distribution (VD):	1.218
Pgp-substrate:	6.552042007446289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.519
CYP2C19-inhibitor:	0.306
CYP2C19-substrate:	0.861
CYP2C9-inhibitor:	0.25
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.833
CYP3A4-substrate:	0.86

ADMET: Excretion

Clearance (CL):	12.934
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.732
Human Hepatotoxicity (H-HT):	0.373
Drug-inuced Liver Injury (DILI):	0.761
AMES Toxicity:	0.323
Rat Oral Acute Toxicity:	0.637
Maximum Recommended Daily Dose:	0.82
Skin Sensitization:	0.967
Carcinogencity:	0.757
Eye Corrosion:	0.011
Eye Irritation:	0.034
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC243065

Natural Product ID:	NPC243065
*Common Name:**	XGPALHIQWWGRFB-TTWUVOALSA-N
IUPAC Name:	n.a.
Synonyms:	4-Dehydro-Withaferin A
Standard InCHIKey:	XGPALHIQWWGRFB-TTWUVOALSA-N
Standard InCHI:	InChI=1S/C28H36O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,24,29H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,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]4[C@@]5(C(=O)C=CC(=O)[C@]5(C)[C@H]3CC[C@]12C)O4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047415
PubChem CID:	165541
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	12
Others	4

Activity Type	# Activity
Cell Line	10
CELL-LINE	1
Individual Protein	1
NON-MOLECULAR	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	18400.0	nM	PMID[456022]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	25400.0	nM	PMID[456022]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	15200.0	nM	PMID[456022]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	12800.0	nM	PMID[456022]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3200.0	nM	PMID[456022]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2100.0	nM	PMID[456022]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	7700.0	nM	PMID[456022]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	1500.0	nM	PMID[456022]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Ratio IC50	=	2.4	n.a.	PMID[456022]
NPT4377	Individual Protein	Heat shock 70 kDa protein 6	Homo sapiens	FC	=	0.79	n.a.	PMID[456023]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	7.3	nM	PMID[456024]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1160.0	nM	PMID[456023]
NPT2	Others	Unspecified		IC50	<	1.0	nM	PMID[456024]
NPT21798	CELL-LINE	ARPE-19	Homo sapiens	IC50	=	32.0	nM	PMID[456024]
NPT2	Others	Unspecified		Ratio IC50	=	4.3	n.a.	PMID[456024]
NPT2	Others	Unspecified		Ratio IC50	>	32.0	n.a.	PMID[456024]

☑ 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 NPC243065 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	237
0.1-0.2	1385
0.2-0.3	4292
0.3-0.4	8572
0.4-0.5	12691
0.5-0.6	7318
0.6-0.7	5896
0.7-0.8	2087
0.8-0.85	172
0.85-0.9	36
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9537	High Similarity	NPC122056
0.9279	High Similarity	NPC140055
0.9279	High Similarity	NPC286528
0.9279	High Similarity	NPC20302
0.9279	High Similarity	NPC167606
0.9196	High Similarity	NPC709
0.9196	High Similarity	NPC50774
0.9115	High Similarity	NPC264954
0.9107	High Similarity	NPC470493
0.9107	High Similarity	NPC312824
0.9107	High Similarity	NPC183580
0.9107	High Similarity	NPC470492
0.9099	High Similarity	NPC67259
0.9099	High Similarity	NPC147912
0.9035	High Similarity	NPC474370
0.9	High Similarity	NPC474315
0.8957	High Similarity	NPC67569
0.8947	High Similarity	NPC470495
0.8919	High Similarity	NPC69291
0.8879	High Similarity	NPC88326
0.8879	High Similarity	NPC23786
0.8879	High Similarity	NPC153700
0.8879	High Similarity	NPC470265
0.8807	High Similarity	NPC91034
0.8803	High Similarity	NPC469789
0.8783	High Similarity	NPC473274
0.8729	High Similarity	NPC470494
0.8729	High Similarity	NPC8369
0.8729	High Similarity	NPC8374
0.8729	High Similarity	NPC3381
0.8696	High Similarity	NPC186525
0.8684	High Similarity	NPC270929
0.8655	High Similarity	NPC293112
0.8644	High Similarity	NPC11895
0.8632	High Similarity	NPC473256
0.8632	High Similarity	NPC470878
0.8621	High Similarity	NPC476960
0.8596	High Similarity	NPC284915
0.8584	High Similarity	NPC476163
0.8571	High Similarity	NPC172154
0.8571	High Similarity	NPC81736
0.8559	High Similarity	NPC170538
0.8534	High Similarity	NPC329736
0.8522	High Similarity	NPC64318
0.8496	Intermediate Similarity	NPC470960
0.8487	Intermediate Similarity	NPC204812
0.8487	Intermediate Similarity	NPC120724
0.8468	Intermediate Similarity	NPC475294
0.8462	Intermediate Similarity	NPC61520
0.8462	Intermediate Similarity	NPC473270
0.8448	Intermediate Similarity	NPC239273
0.8448	Intermediate Similarity	NPC470959
0.8448	Intermediate Similarity	NPC476965
0.8443	Intermediate Similarity	NPC473593
0.8421	Intermediate Similarity	NPC475524
0.8421	Intermediate Similarity	NPC191620
0.8421	Intermediate Similarity	NPC100267
0.8421	Intermediate Similarity	NPC147180
0.8417	Intermediate Similarity	NPC32868
0.8417	Intermediate Similarity	NPC241456
0.8407	Intermediate Similarity	NPC29133
0.8393	Intermediate Similarity	NPC322903
0.8393	Intermediate Similarity	NPC220155
0.839	Intermediate Similarity	NPC476962
0.8376	Intermediate Similarity	NPC257457
0.8376	Intermediate Similarity	NPC311554
0.8362	Intermediate Similarity	NPC148458
0.8348	Intermediate Similarity	NPC159333
0.8348	Intermediate Similarity	NPC25909
0.8348	Intermediate Similarity	NPC472929
0.8347	Intermediate Similarity	NPC473635
0.8333	Intermediate Similarity	NPC470961
0.8306	Intermediate Similarity	NPC231240
0.8305	Intermediate Similarity	NPC475520
0.8305	Intermediate Similarity	NPC472933
0.8291	Intermediate Similarity	NPC471854
0.8291	Intermediate Similarity	NPC472934
0.8279	Intermediate Similarity	NPC156797
0.8279	Intermediate Similarity	NPC473253
0.8261	Intermediate Similarity	NPC264634
0.8261	Intermediate Similarity	NPC285956
0.8257	Intermediate Similarity	NPC474012
0.8257	Intermediate Similarity	NPC476299
0.8246	Intermediate Similarity	NPC37116
0.8241	Intermediate Similarity	NPC253826
0.824	Intermediate Similarity	NPC316915
0.8235	Intermediate Similarity	NPC476961
0.8235	Intermediate Similarity	NPC17938
0.8235	Intermediate Similarity	NPC268530
0.8235	Intermediate Similarity	NPC154491
0.822	Intermediate Similarity	NPC146786
0.8214	Intermediate Similarity	NPC266570
0.8198	Intermediate Similarity	NPC329345
0.8198	Intermediate Similarity	NPC473283
0.8198	Intermediate Similarity	NPC112009
0.8198	Intermediate Similarity	NPC131366
0.8198	Intermediate Similarity	NPC297617
0.8198	Intermediate Similarity	NPC476237
0.8198	Intermediate Similarity	NPC475526
0.8198	Intermediate Similarity	NPC247957
0.8198	Intermediate Similarity	NPC72151
0.8198	Intermediate Similarity	NPC249187
0.819	Intermediate Similarity	NPC472926
0.8182	Intermediate Similarity	NPC282524
0.8174	Intermediate Similarity	NPC317107
0.8167	Intermediate Similarity	NPC159456
0.8167	Intermediate Similarity	NPC46570
0.8167	Intermediate Similarity	NPC4021
0.8165	Intermediate Similarity	NPC478056
0.8165	Intermediate Similarity	NPC98868
0.8165	Intermediate Similarity	NPC316598
0.8158	Intermediate Similarity	NPC87335
0.8158	Intermediate Similarity	NPC475941
0.8158	Intermediate Similarity	NPC474901
0.8158	Intermediate Similarity	NPC475065
0.8151	Intermediate Similarity	NPC42673
0.8145	Intermediate Similarity	NPC470880
0.8145	Intermediate Similarity	NPC221414
0.8142	Intermediate Similarity	NPC473284
0.8142	Intermediate Similarity	NPC329048
0.8142	Intermediate Similarity	NPC330011
0.8142	Intermediate Similarity	NPC472925
0.8142	Intermediate Similarity	NPC44063
0.8136	Intermediate Similarity	NPC55296
0.8136	Intermediate Similarity	NPC472927
0.813	Intermediate Similarity	NPC287423
0.8125	Intermediate Similarity	NPC72255
0.812	Intermediate Similarity	NPC238667
0.812	Intermediate Similarity	NPC470953
0.8108	Intermediate Similarity	NPC155332
0.8108	Intermediate Similarity	NPC136289
0.8108	Intermediate Similarity	NPC114540
0.8108	Intermediate Similarity	NPC320447
0.8108	Intermediate Similarity	NPC32577
0.8103	Intermediate Similarity	NPC317687
0.8103	Intermediate Similarity	NPC236217
0.8103	Intermediate Similarity	NPC475970
0.8103	Intermediate Similarity	NPC221144
0.8099	Intermediate Similarity	NPC107493
0.8099	Intermediate Similarity	NPC269642
0.8095	Intermediate Similarity	NPC469673
0.8095	Intermediate Similarity	NPC58029
0.8087	Intermediate Similarity	NPC470496
0.8083	Intermediate Similarity	NPC251226
0.808	Intermediate Similarity	NPC196921
0.808	Intermediate Similarity	NPC220757
0.8073	Intermediate Similarity	NPC2049
0.807	Intermediate Similarity	NPC475418
0.807	Intermediate Similarity	NPC473482
0.807	Intermediate Similarity	NPC318363
0.807	Intermediate Similarity	NPC295244
0.8067	Intermediate Similarity	NPC473720
0.8067	Intermediate Similarity	NPC113448
0.8065	Intermediate Similarity	NPC473620
0.8053	Intermediate Similarity	NPC60681
0.8053	Intermediate Similarity	NPC189863
0.8053	Intermediate Similarity	NPC1679
0.8053	Intermediate Similarity	NPC257353
0.8036	Intermediate Similarity	NPC95899
0.8036	Intermediate Similarity	NPC478057
0.8036	Intermediate Similarity	NPC180204
0.8036	Intermediate Similarity	NPC476889
0.8036	Intermediate Similarity	NPC475050
0.8036	Intermediate Similarity	NPC311612
0.8031	Intermediate Similarity	NPC476823
0.8018	Intermediate Similarity	NPC476240
0.8018	Intermediate Similarity	NPC476223
0.8018	Intermediate Similarity	NPC207885
0.8018	Intermediate Similarity	NPC112613
0.8018	Intermediate Similarity	NPC81530
0.8018	Intermediate Similarity	NPC115899
0.8018	Intermediate Similarity	NPC473514
0.8018	Intermediate Similarity	NPC224720
0.8017	Intermediate Similarity	NPC472928
0.8016	Intermediate Similarity	NPC476193
0.8016	Intermediate Similarity	NPC34963
0.8	Intermediate Similarity	NPC214644
0.8	Intermediate Similarity	NPC57079
0.8	Intermediate Similarity	NPC475041
0.8	Intermediate Similarity	NPC476966
0.8	Intermediate Similarity	NPC230513
0.8	Intermediate Similarity	NPC2766
0.8	Intermediate Similarity	NPC35109
0.8	Intermediate Similarity	NPC108368
0.7984	Intermediate Similarity	NPC473265
0.7984	Intermediate Similarity	NPC470882
0.7983	Intermediate Similarity	NPC469684
0.7983	Intermediate Similarity	NPC474518
0.7983	Intermediate Similarity	NPC476959
0.7982	Intermediate Similarity	NPC185
0.7982	Intermediate Similarity	NPC470952
0.7982	Intermediate Similarity	NPC242848
0.7982	Intermediate Similarity	NPC131665
0.7982	Intermediate Similarity	NPC255387
0.7967	Intermediate Similarity	NPC470922
0.7966	Intermediate Similarity	NPC474181
0.7965	Intermediate Similarity	NPC137657
0.7965	Intermediate Similarity	NPC189616
0.7963	Intermediate Similarity	NPC470697
0.7949	Intermediate Similarity	NPC71348

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 NPC243065 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	1584
0.2-0.3	3634
0.3-0.4	2451
0.4-0.5	798
0.5-0.6	215
0.6-0.7	153
0.7-0.8	108
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9279	High Similarity	NPD7115	Discovery
0.8333	Intermediate Similarity	NPD6650	Approved
0.8333	Intermediate Similarity	NPD6649	Approved
0.823	Intermediate Similarity	NPD6899	Approved
0.823	Intermediate Similarity	NPD6881	Approved
0.8158	Intermediate Similarity	NPD6373	Approved
0.8158	Intermediate Similarity	NPD6372	Approved
0.8142	Intermediate Similarity	NPD5697	Approved
0.8087	Intermediate Similarity	NPD6883	Approved
0.8087	Intermediate Similarity	NPD7290	Approved
0.8087	Intermediate Similarity	NPD7102	Approved
0.8053	Intermediate Similarity	NPD6675	Approved
0.8053	Intermediate Similarity	NPD6402	Approved
0.8053	Intermediate Similarity	NPD5739	Approved
0.8053	Intermediate Similarity	NPD7128	Approved
0.8017	Intermediate Similarity	NPD6847	Approved
0.8017	Intermediate Similarity	NPD6617	Approved
0.8017	Intermediate Similarity	NPD6869	Approved
0.8017	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD6014	Approved
0.8	Intermediate Similarity	NPD6013	Approved
0.8	Intermediate Similarity	NPD6012	Approved
0.7949	Intermediate Similarity	NPD8297	Approved
0.7949	Intermediate Similarity	NPD6882	Approved
0.7913	Intermediate Similarity	NPD6011	Approved
0.7913	Intermediate Similarity	NPD7320	Approved
0.7909	Intermediate Similarity	NPD6084	Phase 2
0.7909	Intermediate Similarity	NPD6083	Phase 2
0.7826	Intermediate Similarity	NPD5701	Approved
0.7788	Intermediate Similarity	NPD5211	Phase 2
0.7706	Intermediate Similarity	NPD6399	Phase 3
0.7679	Intermediate Similarity	NPD4225	Approved
0.7679	Intermediate Similarity	NPD5696	Approved
0.7652	Intermediate Similarity	NPD5141	Approved
0.7642	Intermediate Similarity	NPD6319	Approved
0.7611	Intermediate Similarity	NPD5285	Approved
0.7611	Intermediate Similarity	NPD7640	Approved
0.7611	Intermediate Similarity	NPD4696	Approved
0.7611	Intermediate Similarity	NPD7639	Approved
0.7611	Intermediate Similarity	NPD5286	Approved
0.7568	Intermediate Similarity	NPD5695	Phase 3
0.7563	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7101	Approved
0.7561	Intermediate Similarity	NPD7100	Approved
0.754	Intermediate Similarity	NPD7492	Approved
0.7522	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD6672	Approved
0.75	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5221	Approved
0.748	Intermediate Similarity	NPD6335	Approved
0.748	Intermediate Similarity	NPD6616	Approved
0.7478	Intermediate Similarity	NPD5226	Approved
0.7478	Intermediate Similarity	NPD5224	Approved
0.7478	Intermediate Similarity	NPD4633	Approved
0.7478	Intermediate Similarity	NPD5225	Approved
0.7459	Intermediate Similarity	NPD6274	Approved
0.7459	Intermediate Similarity	NPD6868	Approved
0.7455	Intermediate Similarity	NPD6079	Approved
0.7455	Intermediate Similarity	NPD5693	Phase 1
0.7434	Intermediate Similarity	NPD4755	Approved
0.7434	Intermediate Similarity	NPD7902	Approved
0.7434	Intermediate Similarity	NPD5173	Approved
0.7422	Intermediate Similarity	NPD7078	Approved
0.7414	Intermediate Similarity	NPD5175	Approved
0.7414	Intermediate Similarity	NPD5174	Approved
0.7411	Intermediate Similarity	NPD5210	Approved
0.7411	Intermediate Similarity	NPD4629	Approved
0.7398	Intermediate Similarity	NPD6317	Approved
0.7391	Intermediate Similarity	NPD5223	Approved
0.7381	Intermediate Similarity	NPD6370	Approved
0.7364	Intermediate Similarity	NPD5785	Approved
0.7339	Intermediate Similarity	NPD6314	Approved
0.7339	Intermediate Similarity	NPD6313	Approved
0.7333	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4634	Approved
0.7323	Intermediate Similarity	NPD7604	Phase 2
0.7321	Intermediate Similarity	NPD7748	Approved
0.7315	Intermediate Similarity	NPD3618	Phase 1
0.7315	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD4700	Approved
0.7302	Intermediate Similarity	NPD6016	Approved
0.7302	Intermediate Similarity	NPD6015	Approved
0.7297	Intermediate Similarity	NPD7515	Phase 2
0.7295	Intermediate Similarity	NPD4632	Approved
0.7288	Intermediate Similarity	NPD6008	Approved
0.7273	Intermediate Similarity	NPD6673	Approved
0.7273	Intermediate Similarity	NPD5328	Approved
0.7273	Intermediate Similarity	NPD6080	Approved
0.7273	Intermediate Similarity	NPD4753	Phase 2
0.7273	Intermediate Similarity	NPD6904	Approved
0.7258	Intermediate Similarity	NPD6009	Approved
0.7257	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5988	Approved
0.7222	Intermediate Similarity	NPD6059	Approved
0.7222	Intermediate Similarity	NPD1694	Approved
0.7179	Intermediate Similarity	NPD7632	Discontinued
0.7168	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7900	Approved
0.7167	Intermediate Similarity	NPD4729	Approved
0.7167	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4730	Approved
0.7165	Intermediate Similarity	NPD5983	Phase 2
0.7165	Intermediate Similarity	NPD6908	Approved
0.7165	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6909	Approved
0.7154	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.713	Intermediate Similarity	NPD4786	Approved
0.7083	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4202	Approved
0.7077	Intermediate Similarity	NPD6336	Discontinued
0.7049	Intermediate Similarity	NPD5247	Approved
0.7049	Intermediate Similarity	NPD5248	Approved
0.7049	Intermediate Similarity	NPD5249	Phase 3
0.7049	Intermediate Similarity	NPD5250	Approved
0.7049	Intermediate Similarity	NPD5251	Approved
0.7045	Intermediate Similarity	NPD7319	Approved
0.7027	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5128	Approved
0.7	Intermediate Similarity	NPD6098	Approved
0.7	Intermediate Similarity	NPD7521	Approved
0.7	Intermediate Similarity	NPD4767	Approved
0.7	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD4768	Approved
0.7	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD5330	Approved
0.7	Intermediate Similarity	NPD6409	Approved
0.7	Intermediate Similarity	NPD7334	Approved
0.6992	Remote Similarity	NPD5215	Approved
0.6992	Remote Similarity	NPD5216	Approved
0.6992	Remote Similarity	NPD5217	Approved
0.6991	Remote Similarity	NPD6050	Approved
0.6991	Remote Similarity	NPD7637	Suspended
0.6991	Remote Similarity	NPD5694	Approved
0.6975	Remote Similarity	NPD4754	Approved
0.6947	Remote Similarity	NPD7507	Approved
0.6944	Remote Similarity	NPD3667	Approved
0.6937	Remote Similarity	NPD3573	Approved
0.6935	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD8328	Phase 3
0.6911	Remote Similarity	NPD5169	Approved
0.6911	Remote Similarity	NPD5135	Approved
0.6911	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6371	Approved
0.6909	Remote Similarity	NPD5329	Approved
0.6909	Remote Similarity	NPD5363	Approved
0.6909	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5692	Phase 3
0.6899	Remote Similarity	NPD7503	Approved
0.6885	Remote Similarity	NPD5168	Approved
0.6875	Remote Similarity	NPD7236	Approved
0.6875	Remote Similarity	NPD6903	Approved
0.687	Remote Similarity	NPD6001	Approved
0.6855	Remote Similarity	NPD5127	Approved
0.6847	Remote Similarity	NPD5690	Phase 2
0.6847	Remote Similarity	NPD5279	Phase 3
0.6842	Remote Similarity	NPD5284	Approved
0.6842	Remote Similarity	NPD6411	Approved
0.6842	Remote Similarity	NPD5281	Approved
0.6818	Remote Similarity	NPD3665	Phase 1
0.6818	Remote Similarity	NPD4197	Approved
0.6818	Remote Similarity	NPD3666	Approved
0.6818	Remote Similarity	NPD3133	Approved
0.6814	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6614	Approved
0.6789	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5779	Approved
0.6783	Remote Similarity	NPD5778	Approved
0.6748	Remote Similarity	NPD6686	Approved
0.6719	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6033	Approved
0.6696	Remote Similarity	NPD5786	Approved
0.6695	Remote Similarity	NPD5959	Approved
0.6693	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD5654	Approved
0.6644	Remote Similarity	NPD7239	Suspended
0.6641	Remote Similarity	NPD8033	Approved
0.6641	Remote Similarity	NPD8513	Phase 3
0.6636	Remote Similarity	NPD4270	Approved
0.6636	Remote Similarity	NPD4269	Approved
0.6636	Remote Similarity	NPD4221	Approved
0.6636	Remote Similarity	NPD4223	Phase 3
0.6615	Remote Similarity	NPD7516	Approved
0.6609	Remote Similarity	NPD5207	Approved
0.6607	Remote Similarity	NPD1696	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