NPASS Compound

Structure

NPC470312 OpenBabel07101718302D 44 49 0 0 1 0 0 0 0 0999 V2000 -3.3951 -5.7471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1337 -6.8829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0361 2.3187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0561 2.3187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6974 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4501 0.4053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3568 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3948 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5461 -0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7807 -0.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7807 -5.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5075 -3.4977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6383 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4365 -5.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0836 -4.2905 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7807 -1.7728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0836 -2.7049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 -1.4700 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7896 0.9800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6974 0.9800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8487 -0.4900 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3948 0.9800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7896 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9409 -0.4900 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0922 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0156 -3.0077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0922 0.9800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5461 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6974 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8487 -0.4900 0.0000 C 0 0 1 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 8.4870 0.9800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6383 -0.4900 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9409 -1.4700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2435 -0.4900 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8084 -2.4317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0156 -3.9877 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9409 1.4700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2435 1.4700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 33 1 0 0 0 0 4 33 1 0 0 0 0 6 35 1 0 0 0 0 8 9 1 0 0 0 0 8 23 1 0 0 0 0 9 26 1 0 0 0 0 10 14 1 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 0 0 0 0 13 34 1 0 0 0 0 14 35 1 0 0 0 0 15 36 1 0 0 0 0 16 19 2 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 18 37 1 0 0 0 0 20 16 1 6 0 0 0 20 42 1 0 0 0 0 21 22 1 1 0 0 0 21 23 1 0 0 0 0 22 31 1 0 0 0 0 23 35 1 6 0 0 0 24 18 1 6 0 0 0 24 28 1 0 0 0 0 24 43 1 0 0 0 0 25 33 1 0 0 0 0 25 34 1 1 0 0 0 26 34 1 1 0 0 0 26 36 1 0 0 0 0 27 33 1 0 0 0 0 27 44 1 1 0 0 0 28 29 1 0 0 0 0 28 38 1 1 0 0 0 29 30 1 0 0 0 0 29 39 1 6 0 0 0 30 32 1 0 0 0 0 30 40 1 1 0 0 0 31 41 2 0 0 0 0 31 42 1 0 0 0 0 32 43 1 0 0 0 0 32 44 1 6 0 0 0 34 5 1 1 0 0 0 35 36 1 1 0 0 0 36 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.4
Volume:	642.286
LogP:	5.54
LogD:	4.858
LogS:	-4.664
# Rotatable Bonds:	5
TPSA:	132.75
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.265
Synthetic Accessibility Score:	5.309
Fsp3:	0.833
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:	-5.254
MDCK Permeability:	1.186872941616457e-05
Pgp-inhibitor:	0.795
Pgp-substrate:	0.322
Human Intestinal Absorption (HIA):	0.144
20% Bioavailability (F20%):	0.271
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	92.76822662353516%
Volume Distribution (VD):	1.268
Pgp-substrate:	3.454861879348755%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.711
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.149
CYP2C9-substrate:	0.433
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.751
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	1.299
Half-life (T1/2):	0.2

ADMET: Toxicity

hERG Blockers:	0.102
Human Hepatotoxicity (H-HT):	0.252
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.725
Carcinogencity:	0.009
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC470312

Natural Product ID:	NPC470312
*Common Name:**	3-O-Beta-D-Glucopyranosyl-Gypensapogenin D
IUPAC Name:	(2S)-2-(2-methylprop-1-enyl)-4-[(3S,5R,8R,9R,10R,13R,14R,17S)-4,4,8,10,14-pentamethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	OOUUEFLYYMXMML-DURLFHHWSA-N
Standard InCHI:	InChI=1S/C36H56O8/c1-19(2)16-20-17-22(31(41)42-20)21-10-14-35(6)23(21)8-9-26-34(5)13-12-27(33(3,4)25(34)11-15-36(26,35)7)44-32-30(40)29(39)28(38)24(18-37)43-32/h16-17,20-21,23-30,32,37-40H,8-15,18H2,1-7H3/t20-,21+,23+,24+,25-,26+,27-,28+,29-,30+,32-,34-,35+,36+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC[C@H]3[C@@]2(C)CC[C@@H]3C2=C[C@@H](OC2=O)C=C(C)C)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1951710
PubChem CID:	57391717
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20104880]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342101]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25895106]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	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	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[476751]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[476751]

☑ 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 NPC470312 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	256
0.1-0.2	1479
0.2-0.3	4447
0.3-0.4	8671
0.4-0.5	11561
0.5-0.6	6750
0.6-0.7	5345
0.7-0.8	3007
0.8-0.85	840
0.85-0.9	236
0.9-0.95	104
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9391	High Similarity	NPC27363
0.9316	High Similarity	NPC240070
0.9316	High Similarity	NPC329784
0.9231	High Similarity	NPC250556
0.9231	High Similarity	NPC469750
0.9204	High Similarity	NPC474483
0.9204	High Similarity	NPC93883
0.916	High Similarity	NPC140092
0.916	High Similarity	NPC232785
0.916	High Similarity	NPC329986
0.916	High Similarity	NPC125077
0.916	High Similarity	NPC276838
0.916	High Similarity	NPC188234
0.9153	High Similarity	NPC471356
0.9153	High Similarity	NPC179412
0.9153	High Similarity	NPC117702
0.9153	High Similarity	NPC471357
0.9153	High Similarity	NPC146456
0.9153	High Similarity	NPC469757
0.913	High Similarity	NPC476150
0.913	High Similarity	NPC476127
0.9115	High Similarity	NPC310341
0.9115	High Similarity	NPC193382
0.9115	High Similarity	NPC199428
0.9115	High Similarity	NPC99620
0.9115	High Similarity	NPC5311
0.9043	High Similarity	NPC236973
0.9043	High Similarity	NPC292467
0.9043	High Similarity	NPC470897
0.9043	High Similarity	NPC304260
0.9043	High Similarity	NPC5883
0.9043	High Similarity	NPC44899
0.9043	High Similarity	NPC30483
0.9043	High Similarity	NPC32177
0.9043	High Similarity	NPC477071
0.9043	High Similarity	NPC469756
0.9043	High Similarity	NPC29639
0.9043	High Similarity	NPC55532
0.9035	High Similarity	NPC84987
0.9035	High Similarity	NPC152615
0.9035	High Similarity	NPC50305
0.9035	High Similarity	NPC27507
0.9035	High Similarity	NPC157376
0.9035	High Similarity	NPC471354
0.9035	High Similarity	NPC309034
0.9035	High Similarity	NPC473852
0.9035	High Similarity	NPC243196
0.9035	High Similarity	NPC244402
0.9035	High Similarity	NPC158344
0.9035	High Similarity	NPC196429
0.9035	High Similarity	NPC471353
0.9035	High Similarity	NPC77319
0.9035	High Similarity	NPC34390
0.9035	High Similarity	NPC474418
0.9035	High Similarity	NPC142066
0.9035	High Similarity	NPC471355
0.9035	High Similarity	NPC87250
0.9035	High Similarity	NPC471351
0.9035	High Similarity	NPC99728
0.9027	High Similarity	NPC69576
0.9027	High Similarity	NPC471633
0.9027	High Similarity	NPC31354
0.9027	High Similarity	NPC84949
0.9	High Similarity	NPC392
0.9	High Similarity	NPC469751
0.9	High Similarity	NPC177524
0.9	High Similarity	NPC469752
0.9	High Similarity	NPC471358
0.9	High Similarity	NPC251866
0.9	High Similarity	NPC89514
0.9	High Similarity	NPC180079
0.9	High Similarity	NPC10823
0.9	High Similarity	NPC219900
0.9	High Similarity	NPC6108
0.9	High Similarity	NPC469755
0.9	High Similarity	NPC70542
0.9	High Similarity	NPC219085
0.9	High Similarity	NPC471359
0.9	High Similarity	NPC471361
0.9	High Similarity	NPC284406
0.9	High Similarity	NPC471360
0.9	High Similarity	NPC197707
0.9	High Similarity	NPC9499
0.9	High Similarity	NPC469754
0.9	High Similarity	NPC469753
0.9	High Similarity	NPC17896
0.9	High Similarity	NPC471352
0.9	High Similarity	NPC86159
0.8966	High Similarity	NPC72260
0.8966	High Similarity	NPC475629
0.8966	High Similarity	NPC475556
0.8957	High Similarity	NPC83287
0.8957	High Similarity	NPC473617
0.8957	High Similarity	NPC473828
0.8957	High Similarity	NPC239293
0.8934	High Similarity	NPC247190
0.8934	High Similarity	NPC477709
0.8934	High Similarity	NPC116075
0.8934	High Similarity	NPC469749
0.8934	High Similarity	NPC476221
0.8934	High Similarity	NPC32793
0.8934	High Similarity	NPC146857
0.8929	High Similarity	NPC285410
0.8929	High Similarity	NPC263827
0.8929	High Similarity	NPC250481
0.8926	High Similarity	NPC253456
0.8926	High Similarity	NPC16569
0.8926	High Similarity	NPC159338
0.8917	High Similarity	NPC311534
0.8898	High Similarity	NPC41129
0.8889	High Similarity	NPC475590
0.8889	High Similarity	NPC475219
0.8889	High Similarity	NPC40749
0.8889	High Similarity	NPC231518
0.8889	High Similarity	NPC120390
0.8889	High Similarity	NPC170084
0.8889	High Similarity	NPC314535
0.8889	High Similarity	NPC476204
0.8889	High Similarity	NPC202051
0.8889	High Similarity	NPC475419
0.8889	High Similarity	NPC474908
0.8889	High Similarity	NPC173555
0.8879	High Similarity	NPC329905
0.887	High Similarity	NPC203862
0.887	High Similarity	NPC290693
0.8862	High Similarity	NPC329636
0.8852	High Similarity	NPC93416
0.8852	High Similarity	NPC42670
0.8852	High Similarity	NPC19124
0.885	High Similarity	NPC470063
0.8843	High Similarity	NPC91
0.8843	High Similarity	NPC476966
0.8843	High Similarity	NPC471407
0.8839	High Similarity	NPC129340
0.8814	High Similarity	NPC193893
0.8814	High Similarity	NPC264336
0.8814	High Similarity	NPC74259
0.8814	High Similarity	NPC474423
0.8803	High Similarity	NPC475136
0.8803	High Similarity	NPC135369
0.8803	High Similarity	NPC474466
0.8803	High Similarity	NPC281840
0.879	High Similarity	NPC194716
0.8783	High Similarity	NPC207637
0.878	High Similarity	NPC225385
0.878	High Similarity	NPC298783
0.878	High Similarity	NPC157817
0.878	High Similarity	NPC104585
0.878	High Similarity	NPC142756
0.8772	High Similarity	NPC260665
0.876	High Similarity	NPC245094
0.875	High Similarity	NPC265655
0.8739	High Similarity	NPC117445
0.8739	High Similarity	NPC208193
0.8739	High Similarity	NPC308262
0.872	High Similarity	NPC329675
0.872	High Similarity	NPC59288
0.8707	High Similarity	NPC473405
0.8699	High Similarity	NPC231240
0.8699	High Similarity	NPC471855
0.8696	High Similarity	NPC220293
0.8696	High Similarity	NPC74727
0.8696	High Similarity	NPC475163
0.8696	High Similarity	NPC472274
0.8696	High Similarity	NPC477580
0.8684	High Similarity	NPC477253
0.8684	High Similarity	NPC471967
0.8678	High Similarity	NPC42399
0.8678	High Similarity	NPC298841
0.8673	High Similarity	NPC101450
0.8667	High Similarity	NPC318135
0.8661	High Similarity	NPC295389
0.8661	High Similarity	NPC88744
0.8661	High Similarity	NPC195708
0.8655	High Similarity	NPC115349
0.8649	High Similarity	NPC473199
0.8644	High Similarity	NPC107607
0.8632	High Similarity	NPC471548
0.8632	High Similarity	NPC291564
0.8632	High Similarity	NPC218093
0.8632	High Similarity	NPC45475
0.8629	High Similarity	NPC316915
0.8621	High Similarity	NPC244127
0.8621	High Similarity	NPC471816
0.8618	High Similarity	NPC173347
0.8609	High Similarity	NPC73986
0.8609	High Similarity	NPC473159
0.8609	High Similarity	NPC251309
0.8607	High Similarity	NPC220838
0.8607	High Similarity	NPC45606
0.8596	High Similarity	NPC292196
0.8596	High Similarity	NPC272242
0.8595	High Similarity	NPC297950
0.8584	High Similarity	NPC473844
0.8584	High Similarity	NPC51947
0.8584	High Similarity	NPC476759
0.8584	High Similarity	NPC167383
0.8584	High Similarity	NPC306746
0.8584	High Similarity	NPC137917
0.8584	High Similarity	NPC8431

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 NPC470312 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	1672
0.2-0.3	3810
0.3-0.4	2287
0.4-0.5	627
0.5-0.6	297
0.6-0.7	170
0.7-0.8	51
0.8-0.85	2
0.85-0.9	11
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD7507	Approved
0.9	High Similarity	NPD7319	Approved
0.9	High Similarity	NPD6686	Approved
0.8966	High Similarity	NPD8377	Approved
0.8966	High Similarity	NPD8294	Approved
0.8957	High Similarity	NPD7328	Approved
0.8957	High Similarity	NPD7327	Approved
0.8889	High Similarity	NPD8033	Approved
0.8889	High Similarity	NPD8296	Approved
0.8889	High Similarity	NPD8380	Approved
0.8889	High Similarity	NPD8335	Approved
0.8889	High Similarity	NPD8379	Approved
0.8889	High Similarity	NPD8378	Approved
0.8879	High Similarity	NPD7516	Approved
0.8448	Intermediate Similarity	NPD8133	Approved
0.8264	Intermediate Similarity	NPD7503	Approved
0.8246	Intermediate Similarity	NPD6412	Phase 2
0.816	Intermediate Similarity	NPD7736	Approved
0.8108	Intermediate Similarity	NPD7638	Approved
0.8036	Intermediate Similarity	NPD7640	Approved
0.8036	Intermediate Similarity	NPD7639	Approved
0.7984	Intermediate Similarity	NPD8328	Phase 3
0.7949	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD8293	Discontinued
0.7787	Intermediate Similarity	NPD7115	Discovery
0.776	Intermediate Similarity	NPD6370	Approved
0.7647	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD7492	Approved
0.7603	Intermediate Similarity	NPD6882	Approved
0.7603	Intermediate Similarity	NPD8297	Approved
0.76	Intermediate Similarity	NPD6054	Approved
0.7578	Intermediate Similarity	NPD6616	Approved
0.7519	Intermediate Similarity	NPD7078	Approved
0.75	Intermediate Similarity	NPD6009	Approved
0.746	Intermediate Similarity	NPD6319	Approved
0.746	Intermediate Similarity	NPD6059	Approved
0.7438	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7632	Discontinued
0.7402	Intermediate Similarity	NPD8517	Approved
0.7402	Intermediate Similarity	NPD6015	Approved
0.7402	Intermediate Similarity	NPD8516	Approved
0.7402	Intermediate Similarity	NPD8515	Approved
0.7402	Intermediate Similarity	NPD6016	Approved
0.7402	Intermediate Similarity	NPD8513	Phase 3
0.7398	Intermediate Similarity	NPD4632	Approved
0.7344	Intermediate Similarity	NPD5988	Approved
0.7328	Intermediate Similarity	NPD4225	Approved
0.7311	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6067	Discontinued
0.7281	Intermediate Similarity	NPD7748	Approved
0.7273	Intermediate Similarity	NPD6881	Approved
0.7273	Intermediate Similarity	NPD7320	Approved
0.7273	Intermediate Similarity	NPD6899	Approved
0.7257	Intermediate Similarity	NPD8034	Phase 2
0.7257	Intermediate Similarity	NPD8035	Phase 2
0.725	Intermediate Similarity	NPD6675	Approved
0.725	Intermediate Similarity	NPD7128	Approved
0.725	Intermediate Similarity	NPD6402	Approved
0.725	Intermediate Similarity	NPD5739	Approved
0.7241	Intermediate Similarity	NPD7902	Approved
0.7236	Intermediate Similarity	NPD6650	Approved
0.7236	Intermediate Similarity	NPD6649	Approved
0.7236	Intermediate Similarity	NPD8130	Phase 1
0.7213	Intermediate Similarity	NPD6372	Approved
0.7213	Intermediate Similarity	NPD6373	Approved
0.719	Intermediate Similarity	NPD5697	Approved
0.719	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7625	Phase 1
0.7168	Intermediate Similarity	NPD6698	Approved
0.7168	Intermediate Similarity	NPD46	Approved
0.7154	Intermediate Similarity	NPD7290	Approved
0.7154	Intermediate Similarity	NPD6883	Approved
0.7154	Intermediate Similarity	NPD7102	Approved
0.7105	Intermediate Similarity	NPD7515	Phase 2
0.7097	Intermediate Similarity	NPD6847	Approved
0.7097	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6869	Approved
0.7097	Intermediate Similarity	NPD6617	Approved
0.7073	Intermediate Similarity	NPD6013	Approved
0.7073	Intermediate Similarity	NPD6012	Approved
0.7073	Intermediate Similarity	NPD6014	Approved
0.7049	Intermediate Similarity	NPD5701	Approved
0.7043	Intermediate Similarity	NPD6399	Phase 3
0.704	Intermediate Similarity	NPD6053	Discontinued
0.7027	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD7604	Phase 2
0.7	Intermediate Similarity	NPD5983	Phase 2
0.6992	Remote Similarity	NPD6011	Approved
0.6992	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7900	Approved
0.6967	Remote Similarity	NPD6008	Approved
0.6957	Remote Similarity	NPD6079	Approved
0.6949	Remote Similarity	NPD6084	Phase 2
0.6949	Remote Similarity	NPD6083	Phase 2
0.694	Remote Similarity	NPD6033	Approved
0.693	Remote Similarity	NPD5328	Approved
0.6917	Remote Similarity	NPD6336	Discontinued
0.6911	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8171	Discontinued
0.6891	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.688	Remote Similarity	NPD4634	Approved
0.686	Remote Similarity	NPD5211	Phase 2
0.6842	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4696	Approved
0.6833	Remote Similarity	NPD5286	Approved
0.6833	Remote Similarity	NPD5285	Approved
0.6825	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3618	Phase 1
0.6807	Remote Similarity	NPD4755	Approved
0.6777	Remote Similarity	NPD5344	Discontinued
0.6752	Remote Similarity	NPD4202	Approved
0.6748	Remote Similarity	NPD5141	Approved
0.6746	Remote Similarity	NPD6371	Approved
0.6744	Remote Similarity	NPD6274	Approved
0.6741	Remote Similarity	NPD8074	Phase 3
0.6724	Remote Similarity	NPD7838	Discovery
0.6723	Remote Similarity	NPD5221	Approved
0.6723	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5222	Approved
0.6721	Remote Similarity	NPD5225	Approved
0.6721	Remote Similarity	NPD5226	Approved
0.6721	Remote Similarity	NPD4633	Approved
0.6721	Remote Similarity	NPD5224	Approved
0.6718	Remote Similarity	NPD7100	Approved
0.6718	Remote Similarity	NPD7101	Approved
0.6696	Remote Similarity	NPD6903	Approved
0.6696	Remote Similarity	NPD5737	Approved
0.6696	Remote Similarity	NPD6672	Approved
0.6694	Remote Similarity	NPD4700	Approved
0.6691	Remote Similarity	NPD8337	Approved
0.6691	Remote Similarity	NPD8336	Approved
0.6687	Remote Similarity	NPD7799	Discontinued
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6641	Remote Similarity	NPD6335	Approved
0.6639	Remote Similarity	NPD5695	Phase 3
0.6639	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5223	Approved
0.6637	Remote Similarity	NPD4786	Approved
0.6619	Remote Similarity	NPD8338	Approved
0.6615	Remote Similarity	NPD6940	Discontinued
0.6615	Remote Similarity	NPD6868	Approved
0.6612	Remote Similarity	NPD5696	Approved
0.6594	Remote Similarity	NPD5956	Approved
0.6587	Remote Similarity	NPD4729	Approved
0.6587	Remote Similarity	NPD4730	Approved
0.6583	Remote Similarity	NPD4697	Phase 3
0.6577	Remote Similarity	NPD7525	Registered
0.6565	Remote Similarity	NPD6317	Approved
0.656	Remote Similarity	NPD4768	Approved
0.656	Remote Similarity	NPD4767	Approved
0.6545	Remote Similarity	NPD6697	Approved
0.6545	Remote Similarity	NPD6115	Approved
0.6545	Remote Similarity	NPD6118	Approved
0.6545	Remote Similarity	NPD6114	Approved
0.6525	Remote Similarity	NPD7637	Suspended
0.6525	Remote Similarity	NPD5693	Phase 1
0.6519	Remote Similarity	NPD7830	Approved
0.6519	Remote Similarity	NPD7829	Approved
0.6515	Remote Similarity	NPD6314	Approved
0.6515	Remote Similarity	NPD6313	Approved
0.65	Remote Similarity	NPD6845	Suspended
0.6496	Remote Similarity	NPD4753	Phase 2
0.6493	Remote Similarity	NPD6909	Approved
0.6493	Remote Similarity	NPD6908	Approved
0.6493	Remote Similarity	NPD6921	Approved
0.6493	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD3666	Approved
0.6491	Remote Similarity	NPD3665	Phase 1
0.6491	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD3133	Approved
0.6484	Remote Similarity	NPD5250	Approved
0.6484	Remote Similarity	NPD5248	Approved
0.6484	Remote Similarity	NPD5251	Approved
0.6484	Remote Similarity	NPD5249	Phase 3
0.6484	Remote Similarity	NPD5247	Approved
0.6466	Remote Similarity	NPD3573	Approved
0.646	Remote Similarity	NPD3667	Approved
0.6457	Remote Similarity	NPD5128	Approved
0.6455	Remote Similarity	NPD6116	Phase 1
0.6435	Remote Similarity	NPD1694	Approved
0.6423	Remote Similarity	NPD6648	Approved
0.64	Remote Similarity	NPD4754	Approved
0.6387	Remote Similarity	NPD7983	Approved
0.6383	Remote Similarity	NPD8449	Approved
0.6364	Remote Similarity	NPD5210	Approved
0.6364	Remote Similarity	NPD6117	Approved
0.6364	Remote Similarity	NPD4629	Approved
0.6356	Remote Similarity	NPD6051	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