NPASS Compound

Structure

NPC475030 OpenBabel07101719152D 30 35 0 0 1 0 0 0 0 0999 V2000 -4.9179 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7946 2.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4582 1.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0514 1.9612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0733 2.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6606 2.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5741 2.5371 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4696 2.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4527 1.1522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 28 1 0 0 0 0 3 4 1 0 0 0 0 3 15 1 0 0 0 0 4 17 1 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 24 1 0 0 0 0 7 8 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 9 14 2 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 16 1 0 0 0 0 15 22 1 1 0 0 0 16 21 1 1 0 0 0 17 18 1 0 0 0 0 17 24 1 6 0 0 0 18 22 1 1 0 0 0 19 21 1 1 0 0 0 19 25 1 0 0 0 0 20 26 2 0 0 0 0 20 29 1 0 0 0 0 21 24 1 1 0 0 0 22 13 1 1 0 0 0 23 11 1 1 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.24
Volume:	419.79
LogP:	2.397
LogD:	2.17
LogS:	-3.713
# Rotatable Bonds:	2
TPSA:	92.29
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	6.585
Fsp3:	0.833
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:	-5.238
MDCK Permeability:	1.373536724713631e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.8
30% Bioavailability (F30%):	0.587

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.665
Plasma Protein Binding (PPB):	76.71199798583984%
Volume Distribution (VD):	2.185
Pgp-substrate:	18.554290771484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.5
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.347
CYP3A4-inhibitor:	0.868
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	10.562
Half-life (T1/2):	0.304

ADMET: Toxicity

hERG Blockers:	0.1
Human Hepatotoxicity (H-HT):	0.472
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.839
Carcinogencity:	0.867
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC475030

Natural Product ID:	NPC475030
*Common Name:**	GFPPTQYNSHRMQH-OELQTSQBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GFPPTQYNSHRMQH-OELQTSQBSA-N
Standard InCHI:	InChI=1S/C24H34O6/c1-21-16(14-9-20(26)29-12-14)5-6-24(21,27)17-4-3-15-11-23(28-2)8-7-22(15,13-30-23)18(17)10-19(21)25/h9,15-19,25,27H,3-8,10-13H2,1-2H3/t15-,16+,17+,18-,19+,21-,22+,23+,24-/m0/s1
SMILES:	CC12C(CCC1(C3CCC4CC5(CCC4(C3CC2O)CO5)OC)O)C6=CC(=O)OC6
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL493006
PubChem CID:	44573471
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides 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
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252914]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19251412]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9165	Asclepias curassavica	Species	Apocynaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	89930.0	nM	PMID[449599]
NPT80	Cell Line	Raji	Homo sapiens	IC50	=	64670.0	nM	PMID[449599]

☑ 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 NPC475030 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	243
0.1-0.2	1706
0.2-0.3	5317
0.3-0.4	12066
0.4-0.5	9913
0.5-0.6	6121
0.6-0.7	4826
0.7-0.8	2137
0.8-0.85	188
0.85-0.9	83
0.9-0.95	96
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC196471
0.95	High Similarity	NPC97487
0.95	High Similarity	NPC189588
0.95	High Similarity	NPC10232
0.95	High Similarity	NPC187302
0.9346	High Similarity	NPC27507
0.9346	High Similarity	NPC87250
0.9346	High Similarity	NPC99728
0.9346	High Similarity	NPC471354
0.9346	High Similarity	NPC158344
0.9346	High Similarity	NPC244402
0.9346	High Similarity	NPC243196
0.9346	High Similarity	NPC50305
0.9346	High Similarity	NPC34390
0.9346	High Similarity	NPC309034
0.9346	High Similarity	NPC84987
0.9346	High Similarity	NPC142066
0.9346	High Similarity	NPC157376
0.9346	High Similarity	NPC471351
0.9346	High Similarity	NPC473852
0.9346	High Similarity	NPC471355
0.9346	High Similarity	NPC471353
0.9346	High Similarity	NPC474418
0.9346	High Similarity	NPC196429
0.9346	High Similarity	NPC77319
0.934	High Similarity	NPC471633
0.934	High Similarity	NPC31354
0.934	High Similarity	NPC69576
0.934	High Similarity	NPC84949
0.93	High Similarity	NPC247701
0.93	High Similarity	NPC295110
0.93	High Similarity	NPC268829
0.93	High Similarity	NPC222875
0.93	High Similarity	NPC25177
0.9259	High Similarity	NPC83287
0.9252	High Similarity	NPC99620
0.9252	High Similarity	NPC5311
0.9252	High Similarity	NPC199428
0.9252	High Similarity	NPC310341
0.9252	High Similarity	NPC193382
0.9167	High Similarity	NPC152615
0.9167	High Similarity	NPC290693
0.9167	High Similarity	NPC93883
0.9126	High Similarity	NPC119855
0.9126	High Similarity	NPC220217
0.9118	High Similarity	NPC160583
0.9091	High Similarity	NPC475556
0.9091	High Similarity	NPC475136
0.9091	High Similarity	NPC474466
0.9091	High Similarity	NPC475629
0.9009	High Similarity	NPC173555
0.9009	High Similarity	NPC314535
0.9	High Similarity	NPC30483
0.9	High Similarity	NPC44899
0.9	High Similarity	NPC29639
0.9	High Similarity	NPC236973
0.9	High Similarity	NPC469756
0.9	High Similarity	NPC5883
0.9	High Similarity	NPC304260
0.9	High Similarity	NPC32177
0.9	High Similarity	NPC292467
0.9	High Similarity	NPC55532
0.9	High Similarity	NPC470897
0.9	High Similarity	NPC329905
0.8991	High Similarity	NPC203862
0.8942	High Similarity	NPC186668
0.8942	High Similarity	NPC472818
0.8932	High Similarity	NPC45897
0.8932	High Similarity	NPC472821
0.8929	High Similarity	NPC264336
0.8919	High Similarity	NPC72260
0.8857	High Similarity	NPC472820
0.885	High Similarity	NPC308262
0.885	High Similarity	NPC208193
0.885	High Similarity	NPC117445
0.8846	High Similarity	NPC472819
0.8839	High Similarity	NPC474908
0.8839	High Similarity	NPC40749
0.8839	High Similarity	NPC120390
0.8839	High Similarity	NPC475590
0.8839	High Similarity	NPC475219
0.8839	High Similarity	NPC231518
0.8839	High Similarity	NPC475419
0.8812	High Similarity	NPC51499
0.8761	High Similarity	NPC474423
0.8761	High Similarity	NPC74259
0.8761	High Similarity	NPC193893
0.8761	High Similarity	NPC115349
0.8739	High Similarity	NPC218093
0.8725	High Similarity	NPC325229
0.8725	High Similarity	NPC275086
0.8684	High Similarity	NPC27363
0.8661	High Similarity	NPC81222
0.8661	High Similarity	NPC153085
0.8661	High Similarity	NPC268326
0.8661	High Similarity	NPC291820
0.8641	High Similarity	NPC477721
0.8641	High Similarity	NPC472826
0.8641	High Similarity	NPC477716
0.8627	High Similarity	NPC231751
0.8621	High Similarity	NPC469757
0.8621	High Similarity	NPC117702
0.8621	High Similarity	NPC471357
0.8621	High Similarity	NPC471356
0.8621	High Similarity	NPC146456
0.8621	High Similarity	NPC179412
0.8598	High Similarity	NPC137462
0.8598	High Similarity	NPC304276
0.8585	High Similarity	NPC51719
0.8584	High Similarity	NPC257610
0.8584	High Similarity	NPC107607
0.8571	High Similarity	NPC120009
0.8559	High Similarity	NPC72772
0.8559	High Similarity	NPC469794
0.8558	High Similarity	NPC176406
0.8558	High Similarity	NPC477717
0.8545	High Similarity	NPC171126
0.8534	High Similarity	NPC250556
0.8534	High Similarity	NPC469750
0.8519	High Similarity	NPC473570
0.8505	High Similarity	NPC471205
0.8475	Intermediate Similarity	NPC9499
0.8475	Intermediate Similarity	NPC86159
0.8475	Intermediate Similarity	NPC469752
0.8475	Intermediate Similarity	NPC17896
0.8475	Intermediate Similarity	NPC471358
0.8475	Intermediate Similarity	NPC180079
0.8475	Intermediate Similarity	NPC89514
0.8475	Intermediate Similarity	NPC471361
0.8475	Intermediate Similarity	NPC219085
0.8475	Intermediate Similarity	NPC469751
0.8475	Intermediate Similarity	NPC10823
0.8475	Intermediate Similarity	NPC284406
0.8475	Intermediate Similarity	NPC469753
0.8475	Intermediate Similarity	NPC471359
0.8475	Intermediate Similarity	NPC251866
0.8475	Intermediate Similarity	NPC70542
0.8475	Intermediate Similarity	NPC469754
0.8475	Intermediate Similarity	NPC6108
0.8475	Intermediate Similarity	NPC471352
0.8475	Intermediate Similarity	NPC471360
0.8475	Intermediate Similarity	NPC197707
0.8475	Intermediate Similarity	NPC469755
0.8462	Intermediate Similarity	NPC240070
0.8462	Intermediate Similarity	NPC329784
0.8462	Intermediate Similarity	NPC251680
0.8455	Intermediate Similarity	NPC44537
0.8447	Intermediate Similarity	NPC477719
0.8447	Intermediate Similarity	NPC477718
0.844	Intermediate Similarity	NPC103491
0.844	Intermediate Similarity	NPC12795
0.844	Intermediate Similarity	NPC177047
0.8431	Intermediate Similarity	NPC276110
0.8426	Intermediate Similarity	NPC473517
0.8421	Intermediate Similarity	NPC470312
0.8396	Intermediate Similarity	NPC112009
0.8396	Intermediate Similarity	NPC281378
0.8381	Intermediate Similarity	NPC474022
0.8381	Intermediate Similarity	NPC11974
0.8349	Intermediate Similarity	NPC128133
0.8349	Intermediate Similarity	NPC206618
0.8333	Intermediate Similarity	NPC475781
0.8333	Intermediate Similarity	NPC475074
0.8333	Intermediate Similarity	NPC93416
0.8333	Intermediate Similarity	NPC105490
0.8333	Intermediate Similarity	NPC201725
0.8333	Intermediate Similarity	NPC477722
0.8333	Intermediate Similarity	NPC122816
0.8319	Intermediate Similarity	NPC125077
0.8319	Intermediate Similarity	NPC329986
0.8319	Intermediate Similarity	NPC140092
0.8319	Intermediate Similarity	NPC188234
0.8319	Intermediate Similarity	NPC276838
0.8319	Intermediate Similarity	NPC232785
0.8317	Intermediate Similarity	NPC130840
0.8317	Intermediate Similarity	NPC329842
0.8302	Intermediate Similarity	NPC68630
0.8302	Intermediate Similarity	NPC228049
0.8302	Intermediate Similarity	NPC52585
0.8286	Intermediate Similarity	NPC324841
0.8269	Intermediate Similarity	NPC177818
0.8264	Intermediate Similarity	NPC247190
0.8264	Intermediate Similarity	NPC146857
0.8264	Intermediate Similarity	NPC116075
0.8264	Intermediate Similarity	NPC469749
0.8264	Intermediate Similarity	NPC32793
0.8261	Intermediate Similarity	NPC135369
0.8257	Intermediate Similarity	NPC61411
0.8257	Intermediate Similarity	NPC38948
0.825	Intermediate Similarity	NPC253456
0.825	Intermediate Similarity	NPC159338
0.825	Intermediate Similarity	NPC16569
0.8241	Intermediate Similarity	NPC473199
0.8235	Intermediate Similarity	NPC7349
0.8235	Intermediate Similarity	NPC311534
0.823	Intermediate Similarity	NPC207637
0.823	Intermediate Similarity	NPC196931
0.823	Intermediate Similarity	NPC232564
0.823	Intermediate Similarity	NPC113425
0.8224	Intermediate Similarity	NPC471888

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 NPC475030 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	1816
0.2-0.3	4191
0.3-0.4	2034
0.4-0.5	467
0.5-0.6	224
0.6-0.7	188
0.7-0.8	11
0.8-0.85	5
0.85-0.9	3
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9259	High Similarity	NPD7328	Approved
0.9259	High Similarity	NPD7327	Approved
0.9174	High Similarity	NPD7516	Approved
0.9009	High Similarity	NPD8296	Approved
0.9009	High Similarity	NPD8378	Approved
0.9009	High Similarity	NPD8379	Approved
0.9009	High Similarity	NPD8335	Approved
0.9009	High Similarity	NPD8380	Approved
0.8919	High Similarity	NPD8294	Approved
0.8919	High Similarity	NPD8377	Approved
0.8839	High Similarity	NPD8033	Approved
0.8544	High Similarity	NPD7638	Approved
0.8534	High Similarity	NPD7507	Approved
0.8475	Intermediate Similarity	NPD7319	Approved
0.8462	Intermediate Similarity	NPD7640	Approved
0.8462	Intermediate Similarity	NPD7639	Approved
0.819	Intermediate Similarity	NPD7503	Approved
0.7798	Intermediate Similarity	NPD7632	Discontinued
0.7611	Intermediate Similarity	NPD6686	Approved
0.7522	Intermediate Similarity	NPD6412	Phase 2
0.75	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.7456	Intermediate Similarity	NPD7320	Approved
0.7436	Intermediate Similarity	NPD8133	Approved
0.7434	Intermediate Similarity	NPD6402	Approved
0.7434	Intermediate Similarity	NPD5739	Approved
0.7434	Intermediate Similarity	NPD6675	Approved
0.7434	Intermediate Similarity	NPD7128	Approved
0.7429	Intermediate Similarity	NPD6051	Approved
0.7398	Intermediate Similarity	NPD7492	Approved
0.7355	Intermediate Similarity	NPD6059	Approved
0.7355	Intermediate Similarity	NPD6054	Approved
0.7339	Intermediate Similarity	NPD6616	Approved
0.7304	Intermediate Similarity	NPD6881	Approved
0.7304	Intermediate Similarity	NPD6899	Approved
0.728	Intermediate Similarity	NPD7078	Approved
0.728	Intermediate Similarity	NPD8293	Discontinued
0.7273	Intermediate Similarity	NPD6084	Phase 2
0.7273	Intermediate Similarity	NPD6083	Phase 2
0.725	Intermediate Similarity	NPD6009	Approved
0.725	Intermediate Similarity	NPD7115	Discovery
0.7241	Intermediate Similarity	NPD6372	Approved
0.7241	Intermediate Similarity	NPD6373	Approved
0.7241	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6370	Approved
0.7228	Intermediate Similarity	NPD7525	Registered
0.7217	Intermediate Similarity	NPD5697	Approved
0.7217	Intermediate Similarity	NPD5701	Approved
0.7206	Intermediate Similarity	NPD7625	Phase 1
0.7203	Intermediate Similarity	NPD6053	Discontinued
0.7179	Intermediate Similarity	NPD7102	Approved
0.7179	Intermediate Similarity	NPD7290	Approved
0.7179	Intermediate Similarity	NPD6883	Approved
0.7154	Intermediate Similarity	NPD6015	Approved
0.7154	Intermediate Similarity	NPD6016	Approved
0.713	Intermediate Similarity	NPD6008	Approved
0.7119	Intermediate Similarity	NPD6649	Approved
0.7119	Intermediate Similarity	NPD6847	Approved
0.7119	Intermediate Similarity	NPD6650	Approved
0.7119	Intermediate Similarity	NPD8130	Phase 1
0.7119	Intermediate Similarity	NPD6617	Approved
0.7119	Intermediate Similarity	NPD6869	Approved
0.7097	Intermediate Similarity	NPD5988	Approved
0.7094	Intermediate Similarity	NPD6013	Approved
0.7094	Intermediate Similarity	NPD6012	Approved
0.7094	Intermediate Similarity	NPD6014	Approved
0.7059	Intermediate Similarity	NPD6928	Phase 2
0.7059	Intermediate Similarity	NPD8297	Approved
0.7054	Intermediate Similarity	NPD4225	Approved
0.7034	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6695	Phase 3
0.7009	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD4632	Approved
0.7	Intermediate Similarity	NPD7748	Approved
0.6975	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7637	Suspended
0.6972	Remote Similarity	NPD7515	Phase 2
0.6964	Remote Similarity	NPD4755	Approved
0.6952	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5695	Phase 3
0.6937	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6319	Approved
0.693	Remote Similarity	NPD5344	Discontinued
0.6916	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4202	Approved
0.6903	Remote Similarity	NPD5696	Approved
0.6887	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5211	Phase 2
0.6852	Remote Similarity	NPD6903	Approved
0.6842	Remote Similarity	NPD5286	Approved
0.6842	Remote Similarity	NPD4700	Approved
0.6842	Remote Similarity	NPD4696	Approved
0.6842	Remote Similarity	NPD5285	Approved
0.6822	Remote Similarity	NPD7334	Approved
0.6822	Remote Similarity	NPD7146	Approved
0.6822	Remote Similarity	NPD6409	Approved
0.6822	Remote Similarity	NPD6684	Approved
0.6822	Remote Similarity	NPD7521	Approved
0.6822	Remote Similarity	NPD5330	Approved
0.6822	Remote Similarity	NPD6033	Approved
0.6818	Remote Similarity	NPD8034	Phase 2
0.6818	Remote Similarity	NPD5693	Phase 1
0.6818	Remote Similarity	NPD8035	Phase 2
0.6814	Remote Similarity	NPD7902	Approved
0.6796	Remote Similarity	NPD7645	Phase 2
0.6792	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4753	Phase 2
0.6789	Remote Similarity	NPD5328	Approved
0.678	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8328	Phase 3
0.6772	Remote Similarity	NPD7604	Phase 2
0.6772	Remote Similarity	NPD6067	Discontinued
0.6759	Remote Similarity	NPD7750	Discontinued
0.6759	Remote Similarity	NPD7524	Approved
0.6757	Remote Similarity	NPD6399	Phase 3
0.6752	Remote Similarity	NPD5141	Approved
0.6748	Remote Similarity	NPD6274	Approved
0.6746	Remote Similarity	NPD5983	Phase 2
0.6731	Remote Similarity	NPD6930	Phase 2
0.6731	Remote Similarity	NPD6931	Approved
0.6724	Remote Similarity	NPD5226	Approved
0.6724	Remote Similarity	NPD5225	Approved
0.6724	Remote Similarity	NPD5224	Approved
0.6724	Remote Similarity	NPD4633	Approved
0.672	Remote Similarity	NPD7101	Approved
0.672	Remote Similarity	NPD7100	Approved
0.6696	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6079	Approved
0.664	Remote Similarity	NPD6335	Approved
0.6638	Remote Similarity	NPD5223	Approved
0.6636	Remote Similarity	NPD6080	Approved
0.6636	Remote Similarity	NPD6904	Approved
0.6636	Remote Similarity	NPD3665	Phase 1
0.6636	Remote Similarity	NPD3666	Approved
0.6636	Remote Similarity	NPD6673	Approved
0.6636	Remote Similarity	NPD3133	Approved
0.6635	Remote Similarity	NPD4195	Approved
0.6635	Remote Similarity	NPD6929	Approved
0.6614	Remote Similarity	NPD6909	Approved
0.6614	Remote Similarity	NPD6908	Approved
0.6612	Remote Similarity	NPD4634	Approved
0.6607	Remote Similarity	NPD8171	Discontinued
0.6604	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7514	Phase 3
0.6569	Remote Similarity	NPD7339	Approved
0.6569	Remote Similarity	NPD6942	Approved
0.656	Remote Similarity	NPD6317	Approved
0.6555	Remote Similarity	NPD4767	Approved
0.6555	Remote Similarity	NPD4768	Approved
0.6549	Remote Similarity	NPD6001	Approved
0.6549	Remote Similarity	NPD7900	Approved
0.6549	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5737	Approved
0.6545	Remote Similarity	NPD6672	Approved
0.6525	Remote Similarity	NPD4754	Approved
0.6518	Remote Similarity	NPD7087	Discontinued
0.6508	Remote Similarity	NPD6313	Approved
0.6508	Remote Similarity	NPD6314	Approved
0.6496	Remote Similarity	NPD4159	Approved
0.6491	Remote Similarity	NPD4629	Approved
0.6491	Remote Similarity	NPD5210	Approved
0.6484	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4786	Approved
0.6466	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4221	Approved
0.6449	Remote Similarity	NPD4223	Phase 3
0.6446	Remote Similarity	NPD4729	Approved
0.6446	Remote Similarity	NPD4730	Approved
0.6446	Remote Similarity	NPD5128	Approved
0.6442	Remote Similarity	NPD6925	Approved
0.6442	Remote Similarity	NPD5776	Phase 2
0.6442	Remote Similarity	NPD6932	Approved
0.6436	Remote Similarity	NPD4243	Approved
0.6435	Remote Similarity	NPD5222	Approved
0.6435	Remote Similarity	NPD5221	Approved
0.6435	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4697	Phase 3
0.6429	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5329	Approved
0.6422	Remote Similarity	NPD6893	Approved
0.6415	Remote Similarity	NPD7332	Phase 2
0.6396	Remote Similarity	NPD5208	Approved
0.6389	Remote Similarity	NPD4788	Approved
0.6381	Remote Similarity	NPD6115	Approved
0.6381	Remote Similarity	NPD6118	Approved
0.6381	Remote Similarity	NPD7145	Approved
0.6381	Remote Similarity	NPD6114	Approved
0.6381	Remote Similarity	NPD6697	Approved
0.6379	Remote Similarity	NPD5173	Approved
0.6372	Remote Similarity	NPD5281	Approved
0.6372	Remote Similarity	NPD5284	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