NPASS Compound

Structure

CID231240 OpenBabel06191716032D 45 51 0 0 1 0 0 0 0 0999 V2000 3.0446 -0.4991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5290 2.9951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1482 2.5421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7058 4.0194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1769 0.5576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0291 0.0656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4387 4.9867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2914 4.4944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8818 3.5105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0291 3.0182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1846 0.7670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5866 1.5416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8518 -1.4754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5828 0.8172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2491 0.4630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3245 2.0330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7339 2.0339 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5182 1.1212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1763 1.5412 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8812 1.5415 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7339 3.0185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3891 1.7291 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8518 -0.4918 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5863 4.4949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2917 3.5103 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.4393 2.0339 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7036 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7036 0.9836 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8518 1.4754 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7227 2.0833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9836 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0290 2.0335 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5866 3.5108 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.4393 3.0185 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7036 -1.9672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7203 4.9949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1577 3.0103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5554 -0.4918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5554 1.4754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8518 2.4590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9918 2.7414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8518 1.4754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6581 2.3872 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 11.2920 2.5262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 4 33 1 0 0 0 0 5 6 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 8 2 0 0 0 0 7 24 1 0 0 0 0 8 25 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 32 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 26 1 0 0 0 0 13 35 1 0 0 0 0 14 18 1 0 0 0 0 14 42 1 0 0 0 0 15 18 2 0 0 0 0 16 2 1 1 0 0 0 16 19 1 0 0 0 0 17 12 1 1 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 30 1 0 0 0 0 19 32 1 6 0 0 0 20 32 1 6 0 0 0 21 33 1 6 0 0 0 22 16 1 1 0 0 0 22 43 1 0 0 0 0 23 13 1 6 0 0 0 23 27 1 0 0 0 0 23 44 1 0 0 0 0 24 33 1 0 0 0 0 24 36 2 0 0 0 0 25 34 1 6 0 0 0 25 37 1 0 0 0 0 26 34 1 6 0 0 0 26 45 1 0 0 0 0 27 28 1 0 0 0 0 27 38 1 1 0 0 0 28 29 1 0 0 0 0 28 39 1 6 0 0 0 29 31 1 0 0 0 0 29 40 1 1 0 0 0 30 41 2 0 0 0 0 30 43 1 0 0 0 0 31 42 1 6 0 0 0 31 44 1 0 0 0 0 32 3 1 6 0 0 0 33 34 1 6 0 0 0 34 45 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	632.32
Volume:	622.871
LogP:	2.206
LogD:	2.519
LogS:	-4.099
# Rotatable Bonds:	6
TPSA:	172.35
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.248
Synthetic Accessibility Score:	6.139
Fsp3:	0.853
Lipinski Rule-of-5:	Rejected
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:	-5.588
MDCK Permeability:	4.579450251185335e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.913
20% Bioavailability (F20%):	0.131
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	67.61537170410156%
Volume Distribution (VD):	0.676
Pgp-substrate:	9.005722045898438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.61
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.767
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.351
CYP3A4-substrate:	0.648

ADMET: Excretion

Clearance (CL):	6.589
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.413
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.282
AMES Toxicity:	0.159
Rat Oral Acute Toxicity:	0.159
Maximum Recommended Daily Dose:	0.549
Skin Sensitization:	0.523
Carcinogencity:	0.696
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC231240

Natural Product ID:	NPC231240
*Common Name:**	Sitoindoside Ix
IUPAC Name:	n.a.
Synonyms:	sitoindoside IX
Standard InCHIKey:	WKCJIGSUKSPCKI-WNXUODGFSA-N
Standard InCHI:	InChI=1S/C34H48O11/c1-15-11-22(43-30(41)18(15)14-42-31-29(40)28(39)27(38)23(13-35)44-31)16(2)19-5-6-20-17-12-26-34(45-26)25(37)8-7-24(36)33(34,4)21(17)9-10-32(19,20)3/h7-8,16-17,19-23,25-29,31,35,37-40H,5-6,9-14H2,1-4H3/t16-,17-,19+,20-,21-,22+,23+,25-,26+,27+,28-,29+,31+,32+,33-,34+/m0/s1
SMILES:	OC[C@H]1O[C@@H](OCC2=C(C)C[C@@H](OC2=O)[C@H]([C@H]2CC[C@@H]3[C@]2(C)CC[C@H]2[C@H]3C[C@@H]3[C@]4([C@]2(C)C(=O)C=C[C@@H]4O)O3)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1934467
PubChem CID:	189586
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
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	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	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT169	Cell Line	B16-F10	Mus musculus	IC50	=	3700.0	nM	PMID[501019]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	8300.0	nM	PMID[501019]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4200.0	nM	PMID[501019]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[501019]
NPT27	Others	Unspecified		IC50	=	5200.0	nM	PMID[501019]

☑ 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 NPC231240 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	292
0.1-0.2	1594
0.2-0.3	4253
0.3-0.4	7547
0.4-0.5	11660
0.5-0.6	7995
0.6-0.7	5591
0.7-0.8	3241
0.8-0.85	413
0.85-0.9	100
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC316915
0.9669	High Similarity	NPC476966
0.9508	High Similarity	NPC473593
0.9339	High Similarity	NPC3381
0.9333	High Similarity	NPC23786
0.9333	High Similarity	NPC470265
0.9268	High Similarity	NPC245094
0.925	High Similarity	NPC67569
0.918	High Similarity	NPC318135
0.912	High Similarity	NPC173347
0.9113	High Similarity	NPC473620
0.9098	High Similarity	NPC469789
0.9091	High Similarity	NPC129434
0.9083	High Similarity	NPC473274
0.904	High Similarity	NPC471407
0.9032	High Similarity	NPC42399
0.9	High Similarity	NPC50774
0.9	High Similarity	NPC709
0.8952	High Similarity	NPC473635
0.8952	High Similarity	NPC293112
0.8934	High Similarity	NPC470878
0.8934	High Similarity	NPC170084
0.8934	High Similarity	NPC476204
0.8934	High Similarity	NPC473256
0.8926	High Similarity	NPC232258
0.8917	High Similarity	NPC286528
0.8917	High Similarity	NPC20302
0.8917	High Similarity	NPC140055
0.8917	High Similarity	NPC167606
0.8898	High Similarity	NPC471855
0.8871	High Similarity	NPC32868
0.8871	High Similarity	NPC8374
0.8871	High Similarity	NPC8369
0.8871	High Similarity	NPC241456
0.8852	High Similarity	NPC474370
0.8843	High Similarity	NPC291564
0.881	High Similarity	NPC311534
0.879	High Similarity	NPC204812
0.879	High Similarity	NPC11895
0.878	High Similarity	NPC202051
0.877	High Similarity	NPC477071
0.877	High Similarity	NPC264954
0.876	High Similarity	NPC470493
0.876	High Similarity	NPC312824
0.876	High Similarity	NPC183580
0.876	High Similarity	NPC470492
0.875	High Similarity	NPC322904
0.875	High Similarity	NPC475444
0.875	High Similarity	NPC183816
0.875	High Similarity	NPC233223
0.875	High Similarity	NPC324933
0.875	High Similarity	NPC319719
0.875	High Similarity	NPC196874
0.875	High Similarity	NPC475177
0.875	High Similarity	NPC473679
0.873	High Similarity	NPC287423
0.873	High Similarity	NPC298841
0.872	High Similarity	NPC172154
0.872	High Similarity	NPC81736
0.871	High Similarity	NPC170538
0.871	High Similarity	NPC88326
0.871	High Similarity	NPC153700
0.8699	High Similarity	NPC48692
0.8699	High Similarity	NPC476150
0.8699	High Similarity	NPC470312
0.8699	High Similarity	NPC476127
0.8689	High Similarity	NPC45475
0.8689	High Similarity	NPC239293
0.8689	High Similarity	NPC473828
0.8689	High Similarity	NPC473617
0.8678	High Similarity	NPC207637
0.8672	High Similarity	NPC43589
0.8672	High Similarity	NPC300655
0.8672	High Similarity	NPC311178
0.8672	High Similarity	NPC222951
0.8667	High Similarity	NPC122056
0.8661	High Similarity	NPC112492
0.8661	High Similarity	NPC472270
0.8661	High Similarity	NPC23020
0.8661	High Similarity	NPC472268
0.8661	High Similarity	NPC472269
0.864	High Similarity	NPC41129
0.8618	High Similarity	NPC473270
0.8618	High Similarity	NPC475834
0.8618	High Similarity	NPC474179
0.8618	High Similarity	NPC476960
0.8607	High Similarity	NPC474483
0.8595	High Similarity	NPC473882
0.8595	High Similarity	NPC147912
0.8595	High Similarity	NPC220293
0.8595	High Similarity	NPC67259
0.8583	High Similarity	NPC470516
0.8571	High Similarity	NPC470494
0.856	High Similarity	NPC28532
0.856	High Similarity	NPC269642
0.855	High Similarity	NPC158350
0.8548	High Similarity	NPC476961
0.8548	High Similarity	NPC281840
0.8548	High Similarity	NPC473130
0.8537	High Similarity	NPC234522
0.8537	High Similarity	NPC186525
0.8537	High Similarity	NPC475913
0.8525	High Similarity	NPC270929
0.8516	High Similarity	NPC45606
0.8516	High Similarity	NPC220838
0.8512	High Similarity	NPC264153
0.8504	High Similarity	NPC174367
0.8504	High Similarity	NPC47113
0.8504	High Similarity	NPC297950
0.8496	Intermediate Similarity	NPC75616
0.8485	Intermediate Similarity	NPC289700
0.8485	Intermediate Similarity	NPC62172
0.848	Intermediate Similarity	NPC204731
0.848	Intermediate Similarity	NPC4021
0.848	Intermediate Similarity	NPC159456
0.848	Intermediate Similarity	NPC46570
0.8468	Intermediate Similarity	NPC61520
0.8468	Intermediate Similarity	NPC475520
0.8462	Intermediate Similarity	NPC155529
0.845	Intermediate Similarity	NPC470880
0.845	Intermediate Similarity	NPC477235
0.8443	Intermediate Similarity	NPC74727
0.8443	Intermediate Similarity	NPC475163
0.8438	Intermediate Similarity	NPC240070
0.8438	Intermediate Similarity	NPC329784
0.8438	Intermediate Similarity	NPC117702
0.8438	Intermediate Similarity	NPC471357
0.8438	Intermediate Similarity	NPC146456
0.8438	Intermediate Similarity	NPC473253
0.8438	Intermediate Similarity	NPC305496
0.8438	Intermediate Similarity	NPC469757
0.843	Intermediate Similarity	NPC210420
0.843	Intermediate Similarity	NPC236217
0.843	Intermediate Similarity	NPC474265
0.8425	Intermediate Similarity	NPC470922
0.8421	Intermediate Similarity	NPC295885
0.8421	Intermediate Similarity	NPC140045
0.8421	Intermediate Similarity	NPC596
0.8417	Intermediate Similarity	NPC52241
0.8417	Intermediate Similarity	NPC475317
0.8417	Intermediate Similarity	NPC154856
0.8413	Intermediate Similarity	NPC156789
0.8413	Intermediate Similarity	NPC107493
0.84	Intermediate Similarity	NPC471406
0.84	Intermediate Similarity	NPC135369
0.84	Intermediate Similarity	NPC241192
0.84	Intermediate Similarity	NPC154491
0.84	Intermediate Similarity	NPC476962
0.84	Intermediate Similarity	NPC268530
0.84	Intermediate Similarity	NPC251226
0.8397	Intermediate Similarity	NPC247190
0.8397	Intermediate Similarity	NPC478151
0.8397	Intermediate Similarity	NPC32793
0.8397	Intermediate Similarity	NPC469749
0.8397	Intermediate Similarity	NPC116075
0.8397	Intermediate Similarity	NPC146857
0.8387	Intermediate Similarity	NPC475632
0.8387	Intermediate Similarity	NPC86020
0.8387	Intermediate Similarity	NPC473720
0.8387	Intermediate Similarity	NPC329736
0.8385	Intermediate Similarity	NPC213634
0.8385	Intermediate Similarity	NPC477197
0.8374	Intermediate Similarity	NPC268954
0.8374	Intermediate Similarity	NPC470075
0.8374	Intermediate Similarity	NPC44170
0.8372	Intermediate Similarity	NPC476859
0.8372	Intermediate Similarity	NPC114306
0.8372	Intermediate Similarity	NPC477490
0.8361	Intermediate Similarity	NPC473159
0.8361	Intermediate Similarity	NPC260665
0.8361	Intermediate Similarity	NPC251309
0.8361	Intermediate Similarity	NPC73986
0.8358	Intermediate Similarity	NPC79250
0.8358	Intermediate Similarity	NPC290746
0.8347	Intermediate Similarity	NPC285410
0.8347	Intermediate Similarity	NPC263827
0.8347	Intermediate Similarity	NPC250481
0.8346	Intermediate Similarity	NPC141215
0.8346	Intermediate Similarity	NPC251998
0.8346	Intermediate Similarity	NPC127656
0.8346	Intermediate Similarity	NPC471089
0.8346	Intermediate Similarity	NPC190065
0.8346	Intermediate Similarity	NPC59288
0.8346	Intermediate Similarity	NPC160084
0.8346	Intermediate Similarity	NPC27363
0.8333	Intermediate Similarity	NPC329636
0.8333	Intermediate Similarity	NPC471234
0.8321	Intermediate Similarity	NPC476193
0.8321	Intermediate Similarity	NPC478150
0.8321	Intermediate Similarity	NPC478152
0.8321	Intermediate Similarity	NPC478154
0.8321	Intermediate Similarity	NPC478153
0.832	Intermediate Similarity	NPC475041
0.832	Intermediate Similarity	NPC161065
0.832	Intermediate Similarity	NPC122971
0.832	Intermediate Similarity	NPC473203
0.8309	Intermediate Similarity	NPC48414
0.8309	Intermediate Similarity	NPC5153
0.8308	Intermediate Similarity	NPC471358
0.8308	Intermediate Similarity	NPC6108

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 NPC231240 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	1699
0.2-0.3	3694
0.3-0.4	2290
0.4-0.5	655
0.5-0.6	328
0.6-0.7	177
0.7-0.8	55
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
0.8917	High Similarity	NPD7115	Discovery
0.8333	Intermediate Similarity	NPD7503	Approved
0.8308	Intermediate Similarity	NPD7319	Approved
0.8217	Intermediate Similarity	NPD7507	Approved
0.8189	Intermediate Similarity	NPD8033	Approved
0.8189	Intermediate Similarity	NPD8513	Phase 3
0.811	Intermediate Similarity	NPD8377	Approved
0.811	Intermediate Similarity	NPD8294	Approved
0.8099	Intermediate Similarity	NPD6686	Approved
0.8092	Intermediate Similarity	NPD7736	Approved
0.8062	Intermediate Similarity	NPD8328	Phase 3
0.8047	Intermediate Similarity	NPD8335	Approved
0.8047	Intermediate Similarity	NPD8517	Approved
0.8047	Intermediate Similarity	NPD8380	Approved
0.8047	Intermediate Similarity	NPD8378	Approved
0.8047	Intermediate Similarity	NPD8296	Approved
0.8047	Intermediate Similarity	NPD8379	Approved
0.8047	Intermediate Similarity	NPD8515	Approved
0.8047	Intermediate Similarity	NPD8516	Approved
0.7953	Intermediate Similarity	NPD7327	Approved
0.7953	Intermediate Similarity	NPD7328	Approved
0.792	Intermediate Similarity	NPD8133	Approved
0.7891	Intermediate Similarity	NPD7516	Approved
0.7886	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD6412	Phase 2
0.7846	Intermediate Similarity	NPD6370	Approved
0.7744	Intermediate Similarity	NPD8293	Discontinued
0.7734	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7492	Approved
0.7692	Intermediate Similarity	NPD6054	Approved
0.7692	Intermediate Similarity	NPD6319	Approved
0.7669	Intermediate Similarity	NPD6616	Approved
0.7612	Intermediate Similarity	NPD7078	Approved
0.7559	Intermediate Similarity	NPD8297	Approved
0.7559	Intermediate Similarity	NPD6882	Approved
0.75	Intermediate Similarity	NPD6016	Approved
0.75	Intermediate Similarity	NPD6015	Approved
0.748	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD6009	Approved
0.746	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5988	Approved
0.7438	Intermediate Similarity	NPD4225	Approved
0.7424	Intermediate Similarity	NPD6059	Approved
0.7402	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7639	Approved
0.7377	Intermediate Similarity	NPD7640	Approved
0.7364	Intermediate Similarity	NPD4632	Approved
0.7344	Intermediate Similarity	NPD6650	Approved
0.7344	Intermediate Similarity	NPD6649	Approved
0.7295	Intermediate Similarity	NPD7638	Approved
0.7266	Intermediate Similarity	NPD6371	Approved
0.7244	Intermediate Similarity	NPD6899	Approved
0.7244	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6881	Approved
0.7226	Intermediate Similarity	NPD8074	Phase 3
0.7222	Intermediate Similarity	NPD6008	Approved
0.7209	Intermediate Similarity	NPD8130	Phase 1
0.7188	Intermediate Similarity	NPD6373	Approved
0.7188	Intermediate Similarity	NPD6372	Approved
0.7165	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5697	Approved
0.7132	Intermediate Similarity	NPD6883	Approved
0.7132	Intermediate Similarity	NPD4634	Approved
0.7132	Intermediate Similarity	NPD7102	Approved
0.7132	Intermediate Similarity	NPD7604	Phase 2
0.7132	Intermediate Similarity	NPD7290	Approved
0.7087	Intermediate Similarity	NPD6402	Approved
0.7087	Intermediate Similarity	NPD5739	Approved
0.7087	Intermediate Similarity	NPD6675	Approved
0.7087	Intermediate Similarity	NPD7128	Approved
0.7077	Intermediate Similarity	NPD6869	Approved
0.7077	Intermediate Similarity	NPD6617	Approved
0.7077	Intermediate Similarity	NPD6847	Approved
0.7073	Intermediate Similarity	NPD7902	Approved
0.7054	Intermediate Similarity	NPD6014	Approved
0.7054	Intermediate Similarity	NPD6012	Approved
0.7054	Intermediate Similarity	NPD6013	Approved
0.704	Intermediate Similarity	NPD5344	Discontinued
0.7025	Intermediate Similarity	NPD6399	Phase 3
0.7016	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6698	Approved
0.7	Intermediate Similarity	NPD46	Approved
0.6985	Remote Similarity	NPD5983	Phase 2
0.6984	Remote Similarity	NPD5211	Phase 2
0.6977	Remote Similarity	NPD6011	Approved
0.6977	Remote Similarity	NPD7320	Approved
0.6967	Remote Similarity	NPD7748	Approved
0.6929	Remote Similarity	NPD6033	Approved
0.6906	Remote Similarity	NPD6336	Discontinued
0.6899	Remote Similarity	NPD5701	Approved
0.6899	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6053	Discontinued
0.6884	Remote Similarity	NPD6067	Discontinued
0.6875	Remote Similarity	NPD5141	Approved
0.685	Remote Similarity	NPD7632	Discontinued
0.6829	Remote Similarity	NPD7900	Approved
0.6829	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5285	Approved
0.6825	Remote Similarity	NPD5286	Approved
0.6825	Remote Similarity	NPD4696	Approved
0.6803	Remote Similarity	NPD7515	Phase 2
0.6803	Remote Similarity	NPD6079	Approved
0.68	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD6084	Phase 2
0.6788	Remote Similarity	NPD7799	Discontinued
0.6783	Remote Similarity	NPD7260	Phase 2
0.6763	Remote Similarity	NPD7829	Approved
0.6763	Remote Similarity	NPD7642	Approved
0.6763	Remote Similarity	NPD7830	Approved
0.6744	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6921	Approved
0.6721	Remote Similarity	NPD7838	Discovery
0.6721	Remote Similarity	NPD5785	Approved
0.6719	Remote Similarity	NPD5224	Approved
0.6719	Remote Similarity	NPD5225	Approved
0.6719	Remote Similarity	NPD5226	Approved
0.6719	Remote Similarity	NPD4633	Approved
0.6715	Remote Similarity	NPD7100	Approved
0.6715	Remote Similarity	NPD7101	Approved
0.6713	Remote Similarity	NPD5956	Approved
0.6693	Remote Similarity	NPD6648	Approved
0.6692	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD5174	Approved
0.6642	Remote Similarity	NPD6335	Approved
0.6641	Remote Similarity	NPD5223	Approved
0.664	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5328	Approved
0.6621	Remote Similarity	NPD8338	Approved
0.6618	Remote Similarity	NPD6274	Approved
0.6614	Remote Similarity	NPD5696	Approved
0.6613	Remote Similarity	NPD4202	Approved
0.6601	Remote Similarity	NPD7625	Phase 1
0.6591	Remote Similarity	NPD4730	Approved
0.6591	Remote Similarity	NPD4729	Approved
0.6587	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5221	Approved
0.6587	Remote Similarity	NPD5222	Approved
0.6573	Remote Similarity	NPD8337	Approved
0.6573	Remote Similarity	NPD8336	Approved
0.6569	Remote Similarity	NPD6317	Approved
0.6562	Remote Similarity	NPD4700	Approved
0.6535	Remote Similarity	NPD5173	Approved
0.6532	Remote Similarity	NPD7983	Approved
0.6529	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6314	Approved
0.6522	Remote Similarity	NPD6313	Approved
0.6508	Remote Similarity	NPD4629	Approved
0.6508	Remote Similarity	NPD5210	Approved
0.6508	Remote Similarity	NPD5695	Phase 3
0.65	Remote Similarity	NPD4786	Approved
0.65	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6868	Approved
0.6493	Remote Similarity	NPD5249	Phase 3
0.6493	Remote Similarity	NPD5248	Approved
0.6493	Remote Similarity	NPD5251	Approved
0.6493	Remote Similarity	NPD5247	Approved
0.6493	Remote Similarity	NPD5250	Approved
0.648	Remote Similarity	NPD5779	Approved
0.648	Remote Similarity	NPD5778	Approved
0.6475	Remote Similarity	NPD3573	Approved
0.6457	Remote Similarity	NPD4697	Phase 3
0.6446	Remote Similarity	NPD1694	Approved
0.6443	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD4767	Approved
0.6439	Remote Similarity	NPD4768	Approved
0.6434	Remote Similarity	NPD8451	Approved
0.6423	Remote Similarity	NPD5737	Approved
0.6423	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6672	Approved
0.64	Remote Similarity	NPD5281	Approved
0.64	Remote Similarity	NPD5284	Approved
0.64	Remote Similarity	NPD5693	Phase 1
0.64	Remote Similarity	NPD6411	Approved
0.6395	Remote Similarity	NPD6845	Suspended
0.6393	Remote Similarity	NPD7334	Approved
0.6393	Remote Similarity	NPD6684	Approved
0.6393	Remote Similarity	NPD5330	Approved
0.6393	Remote Similarity	NPD7521	Approved
0.6393	Remote Similarity	NPD7146	Approved
0.6393	Remote Similarity	NPD6409	Approved
0.6389	Remote Similarity	NPD8448	Approved
0.6383	Remote Similarity	NPD6908	Approved
0.6383	Remote Similarity	NPD6909	Approved
0.6378	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD4753	Phase 2
0.637	Remote Similarity	NPD8391	Approved
0.637	Remote Similarity	NPD8390	Approved
0.637	Remote Similarity	NPD8392	Approved
0.6364	Remote Similarity	NPD8299	Approved
0.6364	Remote Similarity	NPD8341	Approved
0.6364	Remote Similarity	NPD8340	Approved
0.6364	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8342	Approved
0.6357	Remote Similarity	NPD4522	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data