NPASS Compound

Structure

CID257610 OpenBabel06191716062D 35 40 0 0 1 0 0 0 0 0999 V2000 0.4158 2.5025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2980 -0.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6636 -2.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6060 -2.0902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0004 -1.8972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2855 -2.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8212 -1.4230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4646 -3.3187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8212 1.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6427 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4641 -0.4742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4917 -0.5572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5145 2.3195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1064 -1.4230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6426 0.9473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2859 -1.8969 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8218 -1.4228 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6425 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0001 0.9481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9912 -1.2245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8216 -0.4742 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4106 0.7112 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4643 -1.4228 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8214 -0.4744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6434 -1.8969 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1381 3.0336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4733 1.4267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9336 -1.1253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0809 1.5625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6509 -0.9536 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8139 -2.3760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4341 -0.4580 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8211 1.4223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2319 0.7112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 14 1 0 0 0 0 4 20 1 0 0 0 0 5 7 1 0 0 0 0 5 17 1 0 0 0 0 6 8 1 0 0 0 0 6 16 1 0 0 0 0 7 24 1 0 0 0 0 8 25 1 0 0 0 0 9 15 1 0 0 0 0 9 19 1 0 0 0 0 10 15 1 0 0 0 0 10 24 1 0 0 0 0 11 23 1 0 0 0 0 12 14 2 0 0 0 0 12 33 1 0 0 0 0 13 27 2 0 0 0 0 13 34 1 0 0 0 0 14 16 1 0 0 0 0 15 28 1 6 0 0 0 16 23 1 6 0 0 0 17 21 1 0 0 0 0 17 25 1 1 0 0 0 18 11 1 1 0 0 0 18 21 1 0 0 0 0 18 35 1 0 0 0 0 19 26 1 6 0 0 0 19 34 1 0 0 0 0 20 29 2 0 0 0 0 20 33 1 0 0 0 0 21 26 1 6 0 0 0 22 26 1 6 0 0 0 22 30 1 0 0 0 0 22 35 1 0 0 0 0 23 25 1 6 0 0 0 24 26 1 6 0 0 0 24 31 1 0 0 0 0 25 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.22
Volume:	475.48
LogP:	0.929
LogD:	0.454
LogS:	-3.299
# Rotatable Bonds:	3
TPSA:	146.66
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	5.795
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.954
MDCK Permeability:	7.042290962999687e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.07
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.25
Plasma Protein Binding (PPB):	70.35091400146484%
Volume Distribution (VD):	0.455
Pgp-substrate:	21.855823516845703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.393
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.194
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	2.619
Half-life (T1/2):	0.524

ADMET: Toxicity

hERG Blockers:	0.301
Human Hepatotoxicity (H-HT):	0.397
Drug-inuced Liver Injury (DILI):	0.172
AMES Toxicity:	0.227
Rat Oral Acute Toxicity:	0.972
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.276
Carcinogencity:	0.957
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC257610

Natural Product ID:	NPC257610
*Common Name:**	Bryophyllin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IJJFGJIZGZSCBF-LMFPGIEDSA-N
Standard InCHI:	InChI=1S/C26H34O9/c1-13(27)34-19-9-15(28)10-24(31)7-5-17-21-18(35-22(30)26(19,21)24)11-23(2)16(6-8-25(17,23)32)14-3-4-20(29)33-12-14/h3-4,12,15-19,21-22,28,30-32H,5-11H2,1-2H3/t15-,16+,17+,18+,19+,21+,22-,23+,24-,25-,26+/m0/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H](C[C@]2(CC[C@@H]3[C@@H]4[C@@H](C[C@]5(C)[C@H](CC[C@]35O)c3ccc(=O)oc3)O[C@@H]([C@]124)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486882
PubChem CID:	44575928
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001557] Bufanolides 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
NPO21454	Iodes cirrhosa	Species	Icacinaceae	Eukaryota	root	n.a.	n.a.	PMID[18327912]
NPO11343	Bryophyllum pinnatum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607348]
NPO21331	Syzygium samarangense	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15386	Bryophyllum pinnatum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18228	Cycas beddomei	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15386	Bryophyllum pinnatum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21331	Syzygium samarangense	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20444	Corticium caeruleum	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18228	Cycas beddomei	Species	Cycadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14318	Lespedeza davidii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21331	Syzygium samarangense	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18024	Acacia pruinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11343	Bryophyllum pinnatum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21454	Iodes cirrhosa	Species	Icacinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28293	Aegilops geniculata	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15386	Bryophyllum pinnatum	Species	Crassulaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	<	80.0	ng/ml	PMID[495114]

☑ 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 NPC257610 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	387
0.1-0.2	1482
0.2-0.3	2898
0.3-0.4	5661
0.4-0.5	10458
0.5-0.6	9957
0.6-0.7	9542
0.7-0.8	2021
0.8-0.85	219
0.85-0.9	40
0.9-0.95	31
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9182	High Similarity	NPC12795
0.9107	High Similarity	NPC171126
0.9018	High Similarity	NPC44537
0.9	High Similarity	NPC304276
0.9	High Similarity	NPC137462
0.8966	High Similarity	NPC41123
0.8966	High Similarity	NPC114939
0.8966	High Similarity	NPC145074
0.8839	High Similarity	NPC103491
0.8818	High Similarity	NPC295843
0.8793	High Similarity	NPC83287
0.8772	High Similarity	NPC154815
0.875	High Similarity	NPC75389
0.8739	High Similarity	NPC475074
0.8718	High Similarity	NPC213761
0.8718	High Similarity	NPC35171
0.8707	High Similarity	NPC50305
0.8707	High Similarity	NPC473852
0.8707	High Similarity	NPC474418
0.8707	High Similarity	NPC243196
0.8707	High Similarity	NPC27507
0.8707	High Similarity	NPC34390
0.8707	High Similarity	NPC142066
0.8707	High Similarity	NPC196429
0.8707	High Similarity	NPC77319
0.8707	High Similarity	NPC158344
0.8707	High Similarity	NPC471353
0.8707	High Similarity	NPC471351
0.8707	High Similarity	NPC87250
0.8707	High Similarity	NPC309034
0.8707	High Similarity	NPC471354
0.8707	High Similarity	NPC244402
0.8707	High Similarity	NPC84987
0.8707	High Similarity	NPC157376
0.8707	High Similarity	NPC471355
0.8707	High Similarity	NPC99728
0.8684	High Similarity	NPC247760
0.8661	High Similarity	NPC275060
0.8655	High Similarity	NPC471082
0.8655	High Similarity	NPC196130
0.8644	High Similarity	NPC112936
0.8636	High Similarity	NPC171014
0.8632	High Similarity	NPC16701
0.8621	High Similarity	NPC99620
0.8621	High Similarity	NPC193382
0.8621	High Similarity	NPC5311
0.8621	High Similarity	NPC199428
0.8621	High Similarity	NPC310341
0.8596	High Similarity	NPC183603
0.8595	High Similarity	NPC179261
0.8584	High Similarity	NPC475030
0.8571	High Similarity	NPC233500
0.8571	High Similarity	NPC79298
0.8571	High Similarity	NPC43063
0.8559	High Similarity	NPC278681
0.8547	High Similarity	NPC93883
0.8547	High Similarity	NPC157380
0.8547	High Similarity	NPC152615
0.8534	High Similarity	NPC471633
0.8534	High Similarity	NPC31354
0.8534	High Similarity	NPC84949
0.8534	High Similarity	NPC69576
0.85	High Similarity	NPC264336
0.8487	Intermediate Similarity	NPC475556
0.8487	Intermediate Similarity	NPC474466
0.8487	Intermediate Similarity	NPC475629
0.8487	Intermediate Similarity	NPC475136
0.8482	Intermediate Similarity	NPC218158
0.8468	Intermediate Similarity	NPC160583
0.8468	Intermediate Similarity	NPC97487
0.8468	Intermediate Similarity	NPC189588
0.8468	Intermediate Similarity	NPC10232
0.8468	Intermediate Similarity	NPC196471
0.8468	Intermediate Similarity	NPC187302
0.8448	Intermediate Similarity	NPC241977
0.843	Intermediate Similarity	NPC55602
0.8425	Intermediate Similarity	NPC62172
0.8425	Intermediate Similarity	NPC289700
0.8417	Intermediate Similarity	NPC314535
0.8417	Intermediate Similarity	NPC173555
0.8413	Intermediate Similarity	NPC248703
0.8403	Intermediate Similarity	NPC32177
0.8403	Intermediate Similarity	NPC292467
0.8403	Intermediate Similarity	NPC55532
0.8403	Intermediate Similarity	NPC304260
0.8403	Intermediate Similarity	NPC30483
0.8403	Intermediate Similarity	NPC469756
0.8403	Intermediate Similarity	NPC236973
0.8403	Intermediate Similarity	NPC29639
0.8403	Intermediate Similarity	NPC219656
0.8403	Intermediate Similarity	NPC5883
0.8403	Intermediate Similarity	NPC329905
0.8403	Intermediate Similarity	NPC44899
0.8403	Intermediate Similarity	NPC470897
0.839	Intermediate Similarity	NPC290693
0.839	Intermediate Similarity	NPC203862
0.839	Intermediate Similarity	NPC185287
0.8378	Intermediate Similarity	NPC471889
0.8333	Intermediate Similarity	NPC72260
0.8319	Intermediate Similarity	NPC119855
0.8319	Intermediate Similarity	NPC220217
0.8319	Intermediate Similarity	NPC146786
0.8305	Intermediate Similarity	NPC113425
0.8305	Intermediate Similarity	NPC232564
0.8304	Intermediate Similarity	NPC471450
0.8295	Intermediate Similarity	NPC75616
0.8288	Intermediate Similarity	NPC295110
0.8288	Intermediate Similarity	NPC25177
0.8288	Intermediate Similarity	NPC222875
0.8288	Intermediate Similarity	NPC268829
0.8288	Intermediate Similarity	NPC247701
0.8279	Intermediate Similarity	NPC308262
0.8279	Intermediate Similarity	NPC117445
0.8279	Intermediate Similarity	NPC219804
0.8279	Intermediate Similarity	NPC208193
0.8264	Intermediate Similarity	NPC475590
0.8264	Intermediate Similarity	NPC475419
0.8264	Intermediate Similarity	NPC474908
0.8264	Intermediate Similarity	NPC120390
0.8264	Intermediate Similarity	NPC40749
0.8264	Intermediate Similarity	NPC231518
0.8264	Intermediate Similarity	NPC475219
0.8264	Intermediate Similarity	NPC312481
0.8254	Intermediate Similarity	NPC155529
0.825	Intermediate Similarity	NPC153085
0.825	Intermediate Similarity	NPC268326
0.8246	Intermediate Similarity	NPC109376
0.824	Intermediate Similarity	NPC221414
0.823	Intermediate Similarity	NPC165969
0.8205	Intermediate Similarity	NPC231797
0.8197	Intermediate Similarity	NPC193893
0.8197	Intermediate Similarity	NPC474423
0.8197	Intermediate Similarity	NPC115349
0.8197	Intermediate Similarity	NPC74259
0.819	Intermediate Similarity	NPC16270
0.8182	Intermediate Similarity	NPC184555
0.8182	Intermediate Similarity	NPC135369
0.8174	Intermediate Similarity	NPC224660
0.8174	Intermediate Similarity	NPC470024
0.8167	Intermediate Similarity	NPC218093
0.8158	Intermediate Similarity	NPC172867
0.8142	Intermediate Similarity	NPC472821
0.8142	Intermediate Similarity	NPC45897
0.8142	Intermediate Similarity	NPC471887
0.8142	Intermediate Similarity	NPC471888
0.8142	Intermediate Similarity	NPC471885
0.8142	Intermediate Similarity	NPC471886
0.8142	Intermediate Similarity	NPC120009
0.813	Intermediate Similarity	NPC41129
0.813	Intermediate Similarity	NPC27363
0.813	Intermediate Similarity	NPC6193
0.812	Intermediate Similarity	NPC65034
0.812	Intermediate Similarity	NPC208189
0.8108	Intermediate Similarity	NPC278673
0.8103	Intermediate Similarity	NPC473570
0.8099	Intermediate Similarity	NPC291820
0.8099	Intermediate Similarity	NPC81222
0.8087	Intermediate Similarity	NPC471205
0.8087	Intermediate Similarity	NPC475781
0.808	Intermediate Similarity	NPC469757
0.808	Intermediate Similarity	NPC117702
0.808	Intermediate Similarity	NPC471357
0.808	Intermediate Similarity	NPC471356
0.808	Intermediate Similarity	NPC179412
0.808	Intermediate Similarity	NPC146456
0.8062	Intermediate Similarity	NPC158350
0.8053	Intermediate Similarity	NPC37207
0.8053	Intermediate Similarity	NPC300399
0.8053	Intermediate Similarity	NPC471482
0.8036	Intermediate Similarity	NPC20113
0.8036	Intermediate Similarity	NPC324841
0.8036	Intermediate Similarity	NPC219285
0.8036	Intermediate Similarity	NPC161527
0.8036	Intermediate Similarity	NPC477971
0.8036	Intermediate Similarity	NPC477972
0.8036	Intermediate Similarity	NPC477968
0.8036	Intermediate Similarity	NPC228251
0.8034	Intermediate Similarity	NPC177047
0.8034	Intermediate Similarity	NPC103627
0.8034	Intermediate Similarity	NPC191439
0.8034	Intermediate Similarity	NPC316708
0.8034	Intermediate Similarity	NPC170974
0.8033	Intermediate Similarity	NPC470312
0.8033	Intermediate Similarity	NPC107607
0.8017	Intermediate Similarity	NPC473517
0.8017	Intermediate Similarity	NPC472080
0.8017	Intermediate Similarity	NPC38948
0.8	Intermediate Similarity	NPC250556
0.8	Intermediate Similarity	NPC186668
0.8	Intermediate Similarity	NPC127656
0.8	Intermediate Similarity	NPC51719
0.8	Intermediate Similarity	NPC472818
0.8	Intermediate Similarity	NPC207637
0.8	Intermediate Similarity	NPC471206
0.8	Intermediate Similarity	NPC469750
0.7983	Intermediate Similarity	NPC73050
0.7966	Intermediate Similarity	NPC17791
0.7966	Intermediate Similarity	NPC470026
0.7953	Intermediate Similarity	NPC251866
0.7953	Intermediate Similarity	NPC471358

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 NPC257610 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	881
0.2-0.3	1749
0.3-0.4	2709
0.4-0.5	2194
0.5-0.6	970
0.6-0.7	284
0.7-0.8	32
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD7503	Approved
0.8793	High Similarity	NPD7328	Approved
0.8793	High Similarity	NPD7327	Approved
0.8718	High Similarity	NPD7516	Approved
0.8417	Intermediate Similarity	NPD8335	Approved
0.8417	Intermediate Similarity	NPD8380	Approved
0.8417	Intermediate Similarity	NPD8296	Approved
0.8417	Intermediate Similarity	NPD8379	Approved
0.8417	Intermediate Similarity	NPD8378	Approved
0.8333	Intermediate Similarity	NPD8377	Approved
0.8333	Intermediate Similarity	NPD8294	Approved
0.8264	Intermediate Similarity	NPD8033	Approved
0.8	Intermediate Similarity	NPD7507	Approved
0.7953	Intermediate Similarity	NPD7319	Approved
0.7788	Intermediate Similarity	NPD7638	Approved
0.7719	Intermediate Similarity	NPD7640	Approved
0.7719	Intermediate Similarity	NPD7639	Approved
0.7597	Intermediate Similarity	NPD7736	Approved
0.7344	Intermediate Similarity	NPD6370	Approved
0.7317	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD6686	Approved
0.7231	Intermediate Similarity	NPD7492	Approved
0.7188	Intermediate Similarity	NPD6054	Approved
0.7177	Intermediate Similarity	NPD6053	Discontinued
0.7176	Intermediate Similarity	NPD6616	Approved
0.7143	Intermediate Similarity	NPD7632	Discontinued
0.7131	Intermediate Similarity	NPD6899	Approved
0.7131	Intermediate Similarity	NPD6881	Approved
0.7121	Intermediate Similarity	NPD8293	Discontinued
0.7121	Intermediate Similarity	NPD7078	Approved
0.712	Intermediate Similarity	NPD8133	Approved
0.7097	Intermediate Similarity	NPD6650	Approved
0.7097	Intermediate Similarity	NPD6649	Approved
0.7087	Intermediate Similarity	NPD7115	Discovery
0.7049	Intermediate Similarity	NPD6412	Phase 2
0.7049	Intermediate Similarity	NPD5697	Approved
0.704	Intermediate Similarity	NPD8297	Approved
0.7016	Intermediate Similarity	NPD7290	Approved
0.7016	Intermediate Similarity	NPD7102	Approved
0.7016	Intermediate Similarity	NPD6883	Approved
0.7	Intermediate Similarity	NPD6015	Approved
0.7	Intermediate Similarity	NPD6016	Approved
0.6992	Remote Similarity	NPD7320	Approved
0.6975	Remote Similarity	NPD6648	Approved
0.6967	Remote Similarity	NPD5739	Approved
0.6967	Remote Similarity	NPD7128	Approved
0.6967	Remote Similarity	NPD6675	Approved
0.6967	Remote Similarity	NPD6402	Approved
0.696	Remote Similarity	NPD8130	Phase 1
0.696	Remote Similarity	NPD6869	Approved
0.696	Remote Similarity	NPD6847	Approved
0.696	Remote Similarity	NPD6617	Approved
0.6953	Remote Similarity	NPD6009	Approved
0.6947	Remote Similarity	NPD5988	Approved
0.6935	Remote Similarity	NPD6012	Approved
0.6935	Remote Similarity	NPD6373	Approved
0.6935	Remote Similarity	NPD6372	Approved
0.6935	Remote Similarity	NPD6014	Approved
0.6935	Remote Similarity	NPD6013	Approved
0.6923	Remote Similarity	NPD6319	Approved
0.6923	Remote Similarity	NPD6059	Approved
0.6917	Remote Similarity	NPD5344	Discontinued
0.6855	Remote Similarity	NPD6011	Approved
0.685	Remote Similarity	NPD4632	Approved
0.6829	Remote Similarity	NPD6008	Approved
0.6828	Remote Similarity	NPD7625	Phase 1
0.681	Remote Similarity	NPD7637	Suspended
0.68	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6051	Approved
0.6774	Remote Similarity	NPD5701	Approved
0.675	Remote Similarity	NPD4225	Approved
0.6746	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD8513	Phase 3
0.6727	Remote Similarity	NPD7525	Registered
0.6721	Remote Similarity	NPD5211	Phase 2
0.6696	Remote Similarity	NPD6695	Phase 3
0.6694	Remote Similarity	NPD5286	Approved
0.6694	Remote Similarity	NPD5285	Approved
0.6694	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6642	Remote Similarity	NPD7604	Phase 2
0.6642	Remote Similarity	NPD6067	Discontinued
0.6617	Remote Similarity	NPD8516	Approved
0.6617	Remote Similarity	NPD8517	Approved
0.6617	Remote Similarity	NPD8515	Approved
0.6617	Remote Similarity	NPD5983	Phase 2
0.6613	Remote Similarity	NPD5141	Approved
0.6591	Remote Similarity	NPD7100	Approved
0.6591	Remote Similarity	NPD7101	Approved
0.6585	Remote Similarity	NPD5224	Approved
0.6585	Remote Similarity	NPD5226	Approved
0.6585	Remote Similarity	NPD4633	Approved
0.6585	Remote Similarity	NPD5225	Approved
0.6562	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD6336	Discontinued
0.6532	Remote Similarity	NPD5174	Approved
0.6532	Remote Similarity	NPD5175	Approved
0.6529	Remote Similarity	NPD4755	Approved
0.6519	Remote Similarity	NPD8328	Phase 3
0.6515	Remote Similarity	NPD6335	Approved
0.6508	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5223	Approved
0.65	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6274	Approved
0.6484	Remote Similarity	NPD4634	Approved
0.6481	Remote Similarity	NPD7799	Discontinued
0.6475	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8171	Discontinued
0.6471	Remote Similarity	NPD4202	Approved
0.6466	Remote Similarity	NPD7524	Approved
0.6466	Remote Similarity	NPD4251	Approved
0.6466	Remote Similarity	NPD7750	Discontinued
0.6466	Remote Similarity	NPD4250	Approved
0.6457	Remote Similarity	NPD4730	Approved
0.6457	Remote Similarity	NPD4729	Approved
0.6449	Remote Similarity	NPD6033	Approved
0.6441	Remote Similarity	NPD7838	Discovery
0.6439	Remote Similarity	NPD6317	Approved
0.6429	Remote Similarity	NPD6928	Phase 2
0.6429	Remote Similarity	NPD6930	Phase 2
0.6429	Remote Similarity	NPD7514	Phase 3
0.6429	Remote Similarity	NPD6931	Approved
0.6423	Remote Similarity	NPD4700	Approved
0.6417	Remote Similarity	NPD7748	Approved
0.641	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7902	Approved
0.6391	Remote Similarity	NPD6313	Approved
0.6391	Remote Similarity	NPD6314	Approved
0.6387	Remote Similarity	NPD5284	Approved
0.6387	Remote Similarity	NPD7515	Phase 2
0.6387	Remote Similarity	NPD5281	Approved
0.6387	Remote Similarity	NPD8035	Phase 2
0.6387	Remote Similarity	NPD6079	Approved
0.6387	Remote Similarity	NPD8034	Phase 2
0.6379	Remote Similarity	NPD4249	Approved
0.6364	Remote Similarity	NPD5695	Phase 3
0.6357	Remote Similarity	NPD5247	Approved
0.6357	Remote Similarity	NPD5251	Approved
0.6357	Remote Similarity	NPD5249	Phase 3
0.6357	Remote Similarity	NPD5248	Approved
0.6357	Remote Similarity	NPD5250	Approved
0.6341	Remote Similarity	NPD5696	Approved
0.6339	Remote Similarity	NPD6929	Approved
0.6339	Remote Similarity	NPD4195	Approved
0.6333	Remote Similarity	NPD6399	Phase 3
0.6328	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6932	Approved
0.6303	Remote Similarity	NPD5207	Approved
0.6299	Remote Similarity	NPD4767	Approved
0.6299	Remote Similarity	NPD4768	Approved
0.6293	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD7236	Approved
0.6283	Remote Similarity	NPD7332	Phase 2
0.6271	Remote Similarity	NPD6903	Approved
0.625	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD7145	Approved
0.625	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD6908	Approved
0.625	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7087	Discontinued
0.6241	Remote Similarity	NPD5956	Approved
0.6239	Remote Similarity	NPD6684	Approved
0.6239	Remote Similarity	NPD7521	Approved
0.6239	Remote Similarity	NPD7334	Approved
0.6239	Remote Similarity	NPD5330	Approved
0.6239	Remote Similarity	NPD7146	Approved
0.6239	Remote Similarity	NPD6409	Approved
0.623	Remote Similarity	NPD4629	Approved
0.623	Remote Similarity	NPD5210	Approved
0.6228	Remote Similarity	NPD6902	Approved
0.622	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5328	Approved
0.6218	Remote Similarity	NPD4753	Phase 2
0.6202	Remote Similarity	NPD5128	Approved
0.6197	Remote Similarity	NPD7260	Phase 2
0.6195	Remote Similarity	NPD7645	Phase 2
0.6194	Remote Similarity	NPD7239	Suspended
0.6194	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD5215	Approved
0.6183	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD5217	Approved
0.6183	Remote Similarity	NPD5216	Approved
0.6179	Remote Similarity	NPD5221	Approved
0.6179	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5222	Approved
0.6161	Remote Similarity	NPD6925	Approved
0.6161	Remote Similarity	NPD5776	Phase 2
0.6154	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6893	Approved
0.6148	Remote Similarity	NPD7900	Approved
0.6148	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6001	Approved
0.6142	Remote Similarity	NPD4754	Approved
0.6129	Remote Similarity	NPD5173	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