NPASS Compound

Structure

NPC281840 OpenBabel07101719512D 43 47 0 0 1 0 0 0 0 0999 V2000 -3.3267 3.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7805 4.4101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3536 2.1469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9406 1.9109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4731 4.4354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9325 2.4824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4462 1.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5196 -0.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1343 0.2117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8428 1.8449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3219 1.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6967 0.2482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8682 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6341 3.9341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4241 1.8449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6335 2.4193 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7072 0.9519 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8536 -0.4759 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5407 1.2764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9155 0.2300 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6926 0.0253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6779 1.0025 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8244 1.4785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1221 0.9154 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6487 2.9569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0146 0.9772 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2983 -1.7907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7767 -0.9663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9260 0.9336 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1448 0.9154 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3008 -0.1128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7218 -1.9291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5462 -0.4506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 1.5038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6966 0.1247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5023 2.4810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3211 -1.7761 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7742 -2.6443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2755 -1.8053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7539 -0.9810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8682 1.4531 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 -0.8097 2.4557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 5 14 2 0 0 0 0 6 7 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 10 16 1 0 0 0 0 10 30 1 0 0 0 0 11 17 1 0 0 0 0 11 29 1 0 0 0 0 12 17 1 0 0 0 0 12 31 1 0 0 0 0 13 32 1 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 6 1 1 0 0 0 17 41 1 1 0 0 0 18 13 1 6 0 0 0 18 21 1 0 0 0 0 18 42 1 0 0 0 0 19 29 1 6 0 0 0 19 30 1 0 0 0 0 20 29 1 6 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 33 1 1 0 0 0 22 23 1 0 0 0 0 22 34 1 6 0 0 0 23 26 1 0 0 0 0 23 43 1 1 0 0 0 24 30 1 6 0 0 0 24 35 1 0 0 0 0 25 36 2 0 0 0 0 25 43 1 0 0 0 0 26 41 1 6 0 0 0 26 42 1 0 0 0 0 27 31 1 0 0 0 0 27 37 2 0 0 0 0 27 38 1 0 0 0 0 28 31 1 0 0 0 0 28 39 2 0 0 0 0 28 40 1 0 0 0 0 29 4 1 6 0 0 0 30 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.28
Volume:	594.25
LogP:	1.268
LogD:	0.421
LogS:	-2.257
# Rotatable Bonds:	8
TPSA:	200.28
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.08
Synthetic Accessibility Score:	6.592
Fsp3:	0.774
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:	-6.278
MDCK Permeability:	0.0001596313959453255
Pgp-inhibitor:	0.0
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.935
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.169
Plasma Protein Binding (PPB):	55.821563720703125%
Volume Distribution (VD):	0.326
Pgp-substrate:	29.43488883972168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.262
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	1.252
Half-life (T1/2):	0.897

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.838
Drug-inuced Liver Injury (DILI):	0.716
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.655
Carcinogencity:	0.838
Eye Corrosion:	0.007
Eye Irritation:	0.029
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC281840

Natural Product ID:	NPC281840
*Common Name:**	Sylviside
IUPAC Name:	n.a.
Synonyms:	sylviside
Standard InCHIKey:	PUCBVOBXLMBRDL-IVURCJJDSA-N
Standard InCHI:	InChI=1S/C31H44O12/c1-5-14(2)25(36)43-23-22(34)21(33)18(13-32)42-26(23)41-17-11-29(4)19-7-6-16-10-30(19,24(35)15(16)3)9-8-20(29)31(12-17,27(37)38)28(39)40/h5,16-24,26,32-35H,3,6-13H2,1-2,4H3,(H,37,38)(H,39,40)/b14-5-/t16-,17+,18-,19+,20+,21-,22+,23-,24+,26-,29+,30-/m1/s1
SMILES:	C/C=C(/C)C(=O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1O[C@H]1C[C@@]2(C)[C@@H]3CC[C@@H]4C[C@@]3(CC[C@@H]2C(C1)(C(=O)O)C(=O)O)[C@H](C4=C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508269
PubChem CID:	11657330
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*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
NPO4089	Gnaphalium sylvaticum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562842]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	325300.0	nM	PMID[527221]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1700000.0	nM	PMID[527221]

☑ 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 NPC281840 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	265
0.1-0.2	1660
0.2-0.3	4839
0.3-0.4	8758
0.4-0.5	11156
0.5-0.6	7312
0.6-0.7	5355
0.7-0.8	2769
0.8-0.85	494
0.85-0.9	88
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.887	High Similarity	NPC474483
0.8833	High Similarity	NPC146456
0.8833	High Similarity	NPC469757
0.8833	High Similarity	NPC117702
0.8833	High Similarity	NPC471357
0.8803	High Similarity	NPC470312
0.8739	High Similarity	NPC27363
0.8689	High Similarity	NPC471361
0.8689	High Similarity	NPC469752
0.8689	High Similarity	NPC70542
0.8689	High Similarity	NPC89514
0.8689	High Similarity	NPC9499
0.8689	High Similarity	NPC6108
0.8689	High Similarity	NPC471360
0.8689	High Similarity	NPC86159
0.8689	High Similarity	NPC284406
0.8689	High Similarity	NPC10823
0.8689	High Similarity	NPC251866
0.8689	High Similarity	NPC471352
0.8689	High Similarity	NPC469753
0.8689	High Similarity	NPC469751
0.8689	High Similarity	NPC469755
0.8689	High Similarity	NPC471359
0.8689	High Similarity	NPC469754
0.8689	High Similarity	NPC197707
0.8689	High Similarity	NPC180079
0.8689	High Similarity	NPC219085
0.8689	High Similarity	NPC17896
0.8689	High Similarity	NPC471358
0.8644	High Similarity	NPC476150
0.8644	High Similarity	NPC476127
0.8609	High Similarity	NPC264153
0.8607	High Similarity	NPC311534
0.8595	High Similarity	NPC469750
0.8595	High Similarity	NPC250556
0.8548	High Similarity	NPC231240
0.8547	High Similarity	NPC473304
0.8537	High Similarity	NPC471407
0.8537	High Similarity	NPC476966
0.8525	High Similarity	NPC329784
0.8525	High Similarity	NPC179412
0.8525	High Similarity	NPC240070
0.8525	High Similarity	NPC471356
0.8522	High Similarity	NPC243572
0.8512	High Similarity	NPC318135
0.8509	High Similarity	NPC476766
0.8496	Intermediate Similarity	NPC392
0.8496	Intermediate Similarity	NPC219900
0.8496	Intermediate Similarity	NPC177524
0.848	Intermediate Similarity	NPC116075
0.848	Intermediate Similarity	NPC247190
0.848	Intermediate Similarity	NPC469749
0.848	Intermediate Similarity	NPC146857
0.848	Intermediate Similarity	NPC32793
0.848	Intermediate Similarity	NPC316915
0.8475	Intermediate Similarity	NPC239293
0.8468	Intermediate Similarity	NPC16569
0.8468	Intermediate Similarity	NPC253456
0.8468	Intermediate Similarity	NPC159338
0.8468	Intermediate Similarity	NPC173347
0.8462	Intermediate Similarity	NPC88945
0.8462	Intermediate Similarity	NPC193382
0.8462	Intermediate Similarity	NPC199428
0.8462	Intermediate Similarity	NPC99620
0.8462	Intermediate Similarity	NPC5311
0.8462	Intermediate Similarity	NPC310341
0.8448	Intermediate Similarity	NPC102619
0.8448	Intermediate Similarity	NPC73986
0.8435	Intermediate Similarity	NPC471251
0.8425	Intermediate Similarity	NPC59288
0.8425	Intermediate Similarity	NPC62172
0.8425	Intermediate Similarity	NPC289700
0.8421	Intermediate Similarity	NPC476759
0.8417	Intermediate Similarity	NPC170084
0.8417	Intermediate Similarity	NPC476204
0.8413	Intermediate Similarity	NPC329636
0.84	Intermediate Similarity	NPC233223
0.84	Intermediate Similarity	NPC322904
0.84	Intermediate Similarity	NPC319719
0.84	Intermediate Similarity	NPC93416
0.84	Intermediate Similarity	NPC19124
0.84	Intermediate Similarity	NPC475177
0.84	Intermediate Similarity	NPC471855
0.84	Intermediate Similarity	NPC473679
0.84	Intermediate Similarity	NPC196874
0.84	Intermediate Similarity	NPC183816
0.84	Intermediate Similarity	NPC42670
0.84	Intermediate Similarity	NPC324933
0.84	Intermediate Similarity	NPC475444
0.839	Intermediate Similarity	NPC93883
0.839	Intermediate Similarity	NPC87250
0.839	Intermediate Similarity	NPC471354
0.839	Intermediate Similarity	NPC142066
0.839	Intermediate Similarity	NPC244402
0.839	Intermediate Similarity	NPC243196
0.839	Intermediate Similarity	NPC196429
0.839	Intermediate Similarity	NPC471353
0.839	Intermediate Similarity	NPC34390
0.839	Intermediate Similarity	NPC27507
0.839	Intermediate Similarity	NPC471351
0.839	Intermediate Similarity	NPC158344
0.839	Intermediate Similarity	NPC309034
0.839	Intermediate Similarity	NPC157376
0.839	Intermediate Similarity	NPC50305
0.839	Intermediate Similarity	NPC99728
0.839	Intermediate Similarity	NPC471355
0.839	Intermediate Similarity	NPC152615
0.839	Intermediate Similarity	NPC77319
0.839	Intermediate Similarity	NPC84987
0.839	Intermediate Similarity	NPC473852
0.839	Intermediate Similarity	NPC474418
0.8387	Intermediate Similarity	NPC276838
0.8387	Intermediate Similarity	NPC140092
0.8387	Intermediate Similarity	NPC329986
0.8387	Intermediate Similarity	NPC473593
0.8387	Intermediate Similarity	NPC232785
0.8387	Intermediate Similarity	NPC91
0.8387	Intermediate Similarity	NPC125077
0.8387	Intermediate Similarity	NPC188234
0.8376	Intermediate Similarity	NPC69576
0.8376	Intermediate Similarity	NPC471633
0.8376	Intermediate Similarity	NPC31354
0.8376	Intermediate Similarity	NPC84949
0.8374	Intermediate Similarity	NPC470516
0.8362	Intermediate Similarity	NPC471245
0.8348	Intermediate Similarity	NPC106760
0.8347	Intermediate Similarity	NPC28532
0.8346	Intermediate Similarity	NPC194716
0.8333	Intermediate Similarity	NPC298783
0.8333	Intermediate Similarity	NPC157817
0.8333	Intermediate Similarity	NPC477709
0.8333	Intermediate Similarity	NPC476221
0.8333	Intermediate Similarity	NPC225385
0.8333	Intermediate Similarity	NPC104585
0.8333	Intermediate Similarity	NPC476765
0.8333	Intermediate Similarity	NPC88668
0.832	Intermediate Similarity	NPC43589
0.832	Intermediate Similarity	NPC300655
0.832	Intermediate Similarity	NPC222951
0.832	Intermediate Similarity	NPC311178
0.8319	Intermediate Similarity	NPC83287
0.8306	Intermediate Similarity	NPC23020
0.8306	Intermediate Similarity	NPC112492
0.8306	Intermediate Similarity	NPC472268
0.8306	Intermediate Similarity	NPC114306
0.8306	Intermediate Similarity	NPC472270
0.8306	Intermediate Similarity	NPC472269
0.8306	Intermediate Similarity	NPC477490
0.8306	Intermediate Similarity	NPC245094
0.8305	Intermediate Similarity	NPC44170
0.8305	Intermediate Similarity	NPC268954
0.8305	Intermediate Similarity	NPC469823
0.8305	Intermediate Similarity	NPC469820
0.8295	Intermediate Similarity	NPC75616
0.8293	Intermediate Similarity	NPC47113
0.8293	Intermediate Similarity	NPC174367
0.8291	Intermediate Similarity	NPC471252
0.8291	Intermediate Similarity	NPC132668
0.8291	Intermediate Similarity	NPC260665
0.8281	Intermediate Similarity	NPC329675
0.8276	Intermediate Similarity	NPC329953
0.8276	Intermediate Similarity	NPC122339
0.8276	Intermediate Similarity	NPC11035
0.8276	Intermediate Similarity	NPC272242
0.8264	Intermediate Similarity	NPC129434
0.8264	Intermediate Similarity	NPC40749
0.8264	Intermediate Similarity	NPC202051
0.8261	Intermediate Similarity	NPC8431
0.8261	Intermediate Similarity	NPC131903
0.8261	Intermediate Similarity	NPC471250
0.825	Intermediate Similarity	NPC329905
0.825	Intermediate Similarity	NPC304260
0.825	Intermediate Similarity	NPC5883
0.825	Intermediate Similarity	NPC232258
0.825	Intermediate Similarity	NPC55532
0.825	Intermediate Similarity	NPC319570
0.825	Intermediate Similarity	NPC470897
0.825	Intermediate Similarity	NPC29639
0.825	Intermediate Similarity	NPC236973
0.825	Intermediate Similarity	NPC32177
0.825	Intermediate Similarity	NPC30483
0.825	Intermediate Similarity	NPC469756
0.825	Intermediate Similarity	NPC44899
0.825	Intermediate Similarity	NPC477071
0.825	Intermediate Similarity	NPC292467
0.824	Intermediate Similarity	NPC477196
0.8235	Intermediate Similarity	NPC203862
0.8235	Intermediate Similarity	NPC290693
0.8235	Intermediate Similarity	NPC156651
0.8235	Intermediate Similarity	NPC473968
0.822	Intermediate Similarity	NPC110861
0.822	Intermediate Similarity	NPC477580
0.822	Intermediate Similarity	NPC472274
0.8214	Intermediate Similarity	NPC94919
0.8205	Intermediate Similarity	NPC473303
0.8205	Intermediate Similarity	NPC470543
0.8205	Intermediate Similarity	NPC474927
0.8205	Intermediate Similarity	NPC471244
0.8205	Intermediate Similarity	NPC145625
0.8203	Intermediate Similarity	NPC171619

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 NPC281840 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	1919
0.2-0.3	3859
0.3-0.4	2036
0.4-0.5	577
0.5-0.6	293
0.6-0.7	164
0.7-0.8	34
0.8-0.85	14
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8689	High Similarity	NPD7319	Approved
0.8595	High Similarity	NPD7507	Approved
0.8496	Intermediate Similarity	NPD6686	Approved
0.8448	Intermediate Similarity	NPD8133	Approved
0.8319	Intermediate Similarity	NPD7328	Approved
0.8319	Intermediate Similarity	NPD7327	Approved
0.825	Intermediate Similarity	NPD7516	Approved
0.8182	Intermediate Similarity	NPD8377	Approved
0.8182	Intermediate Similarity	NPD8294	Approved
0.8115	Intermediate Similarity	NPD8379	Approved
0.8115	Intermediate Similarity	NPD8378	Approved
0.8115	Intermediate Similarity	NPD8335	Approved
0.8115	Intermediate Similarity	NPD8380	Approved
0.8115	Intermediate Similarity	NPD8296	Approved
0.8115	Intermediate Similarity	NPD8033	Approved
0.8087	Intermediate Similarity	NPD6412	Phase 2
0.7967	Intermediate Similarity	NPD7503	Approved
0.7874	Intermediate Similarity	NPD7736	Approved
0.784	Intermediate Similarity	NPD8328	Phase 3
0.7787	Intermediate Similarity	NPD7115	Discovery
0.7719	Intermediate Similarity	NPD7640	Approved
0.7719	Intermediate Similarity	NPD7639	Approved
0.7632	Intermediate Similarity	NPD7638	Approved
0.7619	Intermediate Similarity	NPD6370	Approved
0.7519	Intermediate Similarity	NPD8293	Discontinued
0.75	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7492	Approved
0.7478	Intermediate Similarity	NPD4225	Approved
0.746	Intermediate Similarity	NPD6319	Approved
0.746	Intermediate Similarity	NPD6054	Approved
0.7442	Intermediate Similarity	NPD6616	Approved
0.7402	Intermediate Similarity	NPD8517	Approved
0.7402	Intermediate Similarity	NPD8516	Approved
0.7402	Intermediate Similarity	NPD8515	Approved
0.7402	Intermediate Similarity	NPD8513	Phase 3
0.7385	Intermediate Similarity	NPD7078	Approved
0.7323	Intermediate Similarity	NPD6059	Approved
0.7317	Intermediate Similarity	NPD6882	Approved
0.7295	Intermediate Similarity	NPD6371	Approved
0.7273	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6015	Approved
0.7266	Intermediate Similarity	NPD6016	Approved
0.7222	Intermediate Similarity	NPD6009	Approved
0.7209	Intermediate Similarity	NPD5988	Approved
0.7177	Intermediate Similarity	NPD8297	Approved
0.7167	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7632	Discontinued
0.712	Intermediate Similarity	NPD4632	Approved
0.7097	Intermediate Similarity	NPD6650	Approved
0.7097	Intermediate Similarity	NPD6649	Approved
0.7073	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6373	Approved
0.7073	Intermediate Similarity	NPD6372	Approved
0.7016	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6899	Approved
0.6992	Remote Similarity	NPD6881	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	NPD8413	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8034	Phase 2
0.6957	Remote Similarity	NPD8035	Phase 2
0.6911	Remote Similarity	NPD5697	Approved
0.6911	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6067	Discontinued
0.688	Remote Similarity	NPD6883	Approved
0.688	Remote Similarity	NPD4634	Approved
0.688	Remote Similarity	NPD7290	Approved
0.688	Remote Similarity	NPD7102	Approved
0.687	Remote Similarity	NPD46	Approved
0.687	Remote Similarity	NPD6698	Approved
0.6855	Remote Similarity	NPD7320	Approved
0.6825	Remote Similarity	NPD8130	Phase 1
0.6825	Remote Similarity	NPD6617	Approved
0.6825	Remote Similarity	NPD6869	Approved
0.6825	Remote Similarity	NPD6847	Approved
0.6815	Remote Similarity	NPD6033	Approved
0.6807	Remote Similarity	NPD6084	Phase 2
0.6807	Remote Similarity	NPD7902	Approved
0.6807	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD6012	Approved
0.68	Remote Similarity	NPD6014	Approved
0.68	Remote Similarity	NPD6013	Approved
0.6774	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5701	Approved
0.6772	Remote Similarity	NPD6053	Discontinued
0.6767	Remote Similarity	NPD7604	Phase 2
0.6752	Remote Similarity	NPD8171	Discontinued
0.6752	Remote Similarity	NPD6399	Phase 3
0.675	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5983	Phase 2
0.6742	Remote Similarity	NPD6921	Approved
0.6741	Remote Similarity	NPD8074	Phase 3
0.6726	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5785	Approved
0.6721	Remote Similarity	NPD5211	Phase 2
0.672	Remote Similarity	NPD6011	Approved
0.6712	Remote Similarity	NPD7625	Phase 1
0.6696	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7748	Approved
0.6694	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD6336	Discontinued
0.6613	Remote Similarity	NPD5141	Approved
0.6612	Remote Similarity	NPD5696	Approved
0.6594	Remote Similarity	NPD5956	Approved
0.6562	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5286	Approved
0.6557	Remote Similarity	NPD4696	Approved
0.6557	Remote Similarity	NPD5285	Approved
0.6555	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7900	Approved
0.6529	Remote Similarity	NPD4755	Approved
0.6525	Remote Similarity	NPD7637	Suspended
0.6522	Remote Similarity	NPD7521	Approved
0.6522	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD6684	Approved
0.6522	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD7334	Approved
0.6522	Remote Similarity	NPD6409	Approved
0.6504	Remote Similarity	NPD5344	Discontinued
0.65	Remote Similarity	NPD5695	Phase 3
0.6489	Remote Similarity	NPD6274	Approved
0.6489	Remote Similarity	NPD6940	Discontinued
0.6481	Remote Similarity	NPD7799	Discontinued
0.6471	Remote Similarity	NPD4202	Approved
0.6466	Remote Similarity	NPD7100	Approved
0.6466	Remote Similarity	NPD7101	Approved
0.646	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5224	Approved
0.6452	Remote Similarity	NPD5226	Approved
0.6452	Remote Similarity	NPD5225	Approved
0.6452	Remote Similarity	NPD4633	Approved
0.6449	Remote Similarity	NPD8337	Approved
0.6449	Remote Similarity	NPD8336	Approved
0.6423	Remote Similarity	NPD4700	Approved
0.641	Remote Similarity	NPD6903	Approved
0.6404	Remote Similarity	NPD4788	Approved
0.64	Remote Similarity	NPD5175	Approved
0.64	Remote Similarity	NPD5174	Approved
0.6397	Remote Similarity	NPD7830	Approved
0.6397	Remote Similarity	NPD7829	Approved
0.6391	Remote Similarity	NPD6335	Approved
0.6387	Remote Similarity	NPD5693	Phase 1
0.6387	Remote Similarity	NPD7983	Approved
0.6387	Remote Similarity	NPD6079	Approved
0.6379	Remote Similarity	NPD3618	Phase 1
0.6371	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5210	Approved
0.6364	Remote Similarity	NPD4629	Approved
0.6356	Remote Similarity	NPD4753	Phase 2
0.6356	Remote Similarity	NPD5328	Approved
0.6348	Remote Similarity	NPD3133	Approved
0.6348	Remote Similarity	NPD3666	Approved
0.6348	Remote Similarity	NPD3665	Phase 1
0.6333	Remote Similarity	NPD5779	Approved
0.6333	Remote Similarity	NPD5778	Approved
0.6328	Remote Similarity	NPD4730	Approved
0.6328	Remote Similarity	NPD4729	Approved
0.6319	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6317	Approved
0.6312	Remote Similarity	NPD7260	Phase 2
0.6303	Remote Similarity	NPD7838	Discovery
0.6299	Remote Similarity	NPD4767	Approved
0.6299	Remote Similarity	NPD4768	Approved
0.6293	Remote Similarity	NPD5363	Approved
0.6283	Remote Similarity	NPD6928	Phase 2
0.6277	Remote Similarity	NPD7642	Approved
0.6271	Remote Similarity	NPD6672	Approved
0.6271	Remote Similarity	NPD5737	Approved
0.6269	Remote Similarity	NPD6314	Approved
0.6269	Remote Similarity	NPD6313	Approved
0.6268	Remote Similarity	NPD8338	Approved
0.625	Remote Similarity	NPD6411	Approved
0.625	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD6115	Approved
0.625	Remote Similarity	NPD6697	Approved
0.625	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD6908	Approved
0.625	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6118	Approved
0.625	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD6114	Approved
0.6239	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5250	Approved
0.6231	Remote Similarity	NPD5249	Phase 3
0.6231	Remote Similarity	NPD5247	Approved
0.6231	Remote Similarity	NPD5251	Approved
0.6231	Remote Similarity	NPD5248	Approved
0.623	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4522	Approved
0.6218	Remote Similarity	NPD6080	Approved
0.6218	Remote Similarity	NPD6051	Approved
0.6218	Remote Similarity	NPD6673	Approved
0.6218	Remote Similarity	NPD6904	Approved
0.6207	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4786	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