NPASS Compound

Structure

CID81222 OpenBabel06191715422D 41 47 0 0 1 0 0 0 0 0999 V2000 -6.3586 -7.0222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7207 -1.9493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2698 -3.4217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9116 1.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -3.9244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8493 -4.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5485 -2.4527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6997 1.9627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3984 -2.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5496 1.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1998 -2.9503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8501 -2.4529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8496 -1.4715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3984 -5.8862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9929 -4.3240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3997 -6.8183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0973 -3.9253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -2.9430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6992 -2.9431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6992 -3.9244 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8499 -1.4720 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9813 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2477 -5.3958 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8499 1.4720 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1587 -2.7465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2483 -4.4155 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6997 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8493 -2.4524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3984 -3.9248 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5491 -4.4151 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8499 0.4907 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7437 -7.5469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5574 -1.8509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6831 -4.9151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0309 0.9992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0309 1.9805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5496 0.4907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6489 -3.5955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0967 -5.8860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6997 -0.9813 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 16 1 0 0 0 0 3 29 1 0 0 0 0 4 36 1 0 0 0 0 5 6 1 0 0 0 0 5 18 1 0 0 0 0 6 20 1 0 0 0 0 7 9 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 24 1 0 0 0 0 9 29 1 0 0 0 0 10 37 1 0 0 0 0 11 17 2 0 0 0 0 11 25 1 0 0 0 0 12 18 2 0 0 0 0 13 28 1 0 0 0 0 14 23 1 0 0 0 0 14 30 1 0 0 0 0 15 17 1 0 0 0 0 15 38 1 0 0 0 0 16 32 2 0 0 0 0 16 39 1 0 0 0 0 17 26 1 0 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 30 1 1 0 0 0 21 12 1 6 0 0 0 21 22 1 0 0 0 0 21 40 1 0 0 0 0 22 13 1 1 0 0 0 22 41 1 0 0 0 0 23 26 1 0 0 0 0 23 39 1 6 0 0 0 24 31 1 6 0 0 0 24 36 1 0 0 0 0 25 33 2 0 0 0 0 25 38 1 0 0 0 0 26 29 1 6 0 0 0 27 31 1 1 0 0 0 27 37 1 0 0 0 0 27 40 1 0 0 0 0 28 2 1 6 0 0 0 29 30 1 6 0 0 0 30 34 1 6 0 0 0 31 35 1 6 0 0 0 31 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	574.28
Volume:	562.193
LogP:	3.561
LogD:	2.467
LogS:	-4.465
# Rotatable Bonds:	4
TPSA:	137.05
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.363
Synthetic Accessibility Score:	5.779
Fsp3:	0.774
Lipinski Rule-of-5:	Accepted
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:	-5.342
MDCK Permeability:	3.488607762847096e-05
Pgp-inhibitor:	0.586
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.367
20% Bioavailability (F20%):	0.806
30% Bioavailability (F30%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167
Plasma Protein Binding (PPB):	91.21638488769531%
Volume Distribution (VD):	1.15
Pgp-substrate:	6.741286277770996%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.303
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.296
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.194
CYP3A4-inhibitor:	0.339
CYP3A4-substrate:	0.47

ADMET: Excretion

Clearance (CL):	2.377
Half-life (T1/2):	0.215

ADMET: Toxicity

hERG Blockers:	0.099
Human Hepatotoxicity (H-HT):	0.325
Drug-inuced Liver Injury (DILI):	0.628
AMES Toxicity:	0.551
Rat Oral Acute Toxicity:	0.984
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.112
Carcinogencity:	0.233
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC81222

Natural Product ID:	NPC81222
*Common Name:**	Elaeodendroside G
IUPAC Name:	n.a.
Synonyms:	Elaeodendroside G
Standard InCHIKey:	NRVDOTUZYZELQD-JJSCBUTHSA-N
Standard InCHI:	InChI=1S/C31H42O10/c1-16(32)39-23-14-30(34)20-6-5-18-12-21-22(41-31(35)24(36-4)8-10-37-27(31)40-21)13-28(18,2)19(20)7-9-29(30,3)26(23)17-11-25(33)38-15-17/h11-12,19-24,26-27,34-35H,5-10,13-15H2,1-4H3/t19-,20+,21+,22+,23-,24+,26-,27-,28-,29+,30-,31-/m0/s1
SMILES:	CO[C@@H]1CCO[C@@H]2[C@@]1(O)O[C@@H]1C[C@@]3(C)C(=C[C@H]1O2)CC[C@@H]1[C@@H]3CC[C@]2([C@]1(O)C[C@@H]([C@@H]2C1=CC(=O)OC1)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376169
PubChem CID:	44424482
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001691] Steroid esters

*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
NPO30957	Elaeodendron glaucum	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(00)81130-9]
NPO30836	Elaeodendron tangenala	Species	Celastraceae	Eukaryota	n.a.	xylem	n.a.	PMID[17547460]
NPO32451	elaeodendron sp.	Species	Celastraceae	Eukaryota	n.a.	Madagascar rain forest	n.a.	PMID[17547460]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	100.0	nM	PMID[509501]

☑ 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 NPC81222 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	257
0.1-0.2	1740
0.2-0.3	5173
0.3-0.4	11445
0.4-0.5	9818
0.5-0.6	6777
0.6-0.7	4555
0.7-0.8	2305
0.8-0.85	403
0.85-0.9	98
0.9-0.95	112
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC291820
0.9909	High Similarity	NPC107607
0.9908	High Similarity	NPC218093
0.9643	High Similarity	NPC475219
0.9643	High Similarity	NPC231518
0.9636	High Similarity	NPC203862
0.9558	High Similarity	NPC193893
0.9469	High Similarity	NPC40749
0.9464	High Similarity	NPC304260
0.9464	High Similarity	NPC292467
0.9464	High Similarity	NPC44899
0.9464	High Similarity	NPC30483
0.9464	High Similarity	NPC470897
0.9464	High Similarity	NPC236973
0.9464	High Similarity	NPC469756
0.9464	High Similarity	NPC29639
0.9464	High Similarity	NPC5883
0.9464	High Similarity	NPC329905
0.9464	High Similarity	NPC32177
0.9464	High Similarity	NPC55532
0.9381	High Similarity	NPC72260
0.9381	High Similarity	NPC475629
0.9381	High Similarity	NPC475136
0.9381	High Similarity	NPC474466
0.9381	High Similarity	NPC475556
0.9369	High Similarity	NPC5311
0.9369	High Similarity	NPC310341
0.9369	High Similarity	NPC99620
0.9369	High Similarity	NPC193382
0.9369	High Similarity	NPC199428
0.9298	High Similarity	NPC120390
0.9298	High Similarity	NPC475590
0.9298	High Similarity	NPC475419
0.9298	High Similarity	NPC474908
0.9298	High Similarity	NPC314535
0.9298	High Similarity	NPC173555
0.9286	High Similarity	NPC27507
0.9286	High Similarity	NPC87250
0.9286	High Similarity	NPC99728
0.9286	High Similarity	NPC50305
0.9286	High Similarity	NPC34390
0.9286	High Similarity	NPC471355
0.9286	High Similarity	NPC93883
0.9286	High Similarity	NPC158344
0.9286	High Similarity	NPC77319
0.9286	High Similarity	NPC84987
0.9286	High Similarity	NPC471354
0.9286	High Similarity	NPC142066
0.9286	High Similarity	NPC157376
0.9286	High Similarity	NPC471353
0.9286	High Similarity	NPC473852
0.9286	High Similarity	NPC309034
0.9286	High Similarity	NPC243196
0.9286	High Similarity	NPC474418
0.9286	High Similarity	NPC152615
0.9286	High Similarity	NPC244402
0.9286	High Similarity	NPC196429
0.9286	High Similarity	NPC471351
0.9279	High Similarity	NPC471633
0.9279	High Similarity	NPC31354
0.9279	High Similarity	NPC84949
0.9279	High Similarity	NPC69576
0.9217	High Similarity	NPC74259
0.9217	High Similarity	NPC264336
0.9217	High Similarity	NPC115349
0.9217	High Similarity	NPC474423
0.9204	High Similarity	NPC83287
0.9138	High Similarity	NPC308262
0.9138	High Similarity	NPC208193
0.9138	High Similarity	NPC117445
0.9115	High Similarity	NPC290693
0.8908	High Similarity	NPC240070
0.8908	High Similarity	NPC329784
0.887	High Similarity	NPC160888
0.887	High Similarity	NPC475403
0.886	High Similarity	NPC207637
0.8852	High Similarity	NPC104585
0.8852	High Similarity	NPC142756
0.8852	High Similarity	NPC225385
0.8852	High Similarity	NPC157817
0.8852	High Similarity	NPC298783
0.8839	High Similarity	NPC114188
0.8833	High Similarity	NPC311534
0.8814	High Similarity	NPC27363
0.8793	High Similarity	NPC476085
0.8793	High Similarity	NPC195560
0.8793	High Similarity	NPC268326
0.8793	High Similarity	NPC229962
0.8793	High Similarity	NPC473633
0.8793	High Similarity	NPC153085
0.876	High Similarity	NPC329986
0.876	High Similarity	NPC140092
0.876	High Similarity	NPC232785
0.876	High Similarity	NPC125077
0.876	High Similarity	NPC276838
0.876	High Similarity	NPC188234
0.876	High Similarity	NPC91
0.8739	High Similarity	NPC295980
0.8729	High Similarity	NPC471082
0.8729	High Similarity	NPC43842
0.8718	High Similarity	NPC233391
0.8718	High Similarity	NPC207243
0.8718	High Similarity	NPC198325
0.8718	High Similarity	NPC135369
0.8718	High Similarity	NPC50689
0.8696	High Similarity	NPC146652
0.8689	High Similarity	NPC173347
0.8689	High Similarity	NPC16569
0.8689	High Similarity	NPC159338
0.8689	High Similarity	NPC253456
0.8684	High Similarity	NPC144068
0.8673	High Similarity	NPC13190
0.8667	High Similarity	NPC179261
0.8667	High Similarity	NPC469750
0.8667	High Similarity	NPC250556
0.8661	High Similarity	NPC475030
0.8661	High Similarity	NPC14630
0.8661	High Similarity	NPC250089
0.8661	High Similarity	NPC157530
0.8655	High Similarity	NPC106589
0.8655	High Similarity	NPC295133
0.8655	High Similarity	NPC257207
0.8655	High Similarity	NPC202261
0.8618	High Similarity	NPC19124
0.8618	High Similarity	NPC93416
0.8618	High Similarity	NPC42670
0.8596	High Similarity	NPC112274
0.8596	High Similarity	NPC19888
0.8595	High Similarity	NPC117702
0.8595	High Similarity	NPC471356
0.8595	High Similarity	NPC179412
0.8595	High Similarity	NPC471357
0.8595	High Similarity	NPC146456
0.8595	High Similarity	NPC469757
0.8571	High Similarity	NPC472988
0.8571	High Similarity	NPC38217
0.8559	High Similarity	NPC220217
0.8559	High Similarity	NPC242748
0.8559	High Similarity	NPC119855
0.8559	High Similarity	NPC473566
0.8559	High Similarity	NPC475358
0.8559	High Similarity	NPC470312
0.8548	High Similarity	NPC477709
0.8548	High Similarity	NPC476221
0.8548	High Similarity	NPC469749
0.8548	High Similarity	NPC146857
0.8548	High Similarity	NPC247190
0.8548	High Similarity	NPC116075
0.8548	High Similarity	NPC32793
0.8547	High Similarity	NPC475357
0.8534	High Similarity	NPC212660
0.8534	High Similarity	NPC148965
0.8534	High Similarity	NPC63609
0.8534	High Similarity	NPC477031
0.8522	High Similarity	NPC51154
0.8509	High Similarity	NPC473021
0.8509	High Similarity	NPC197231
0.8509	High Similarity	NPC470748
0.8509	High Similarity	NPC472987
0.85	High Similarity	NPC219804
0.8496	Intermediate Similarity	NPC296761
0.8496	Intermediate Similarity	NPC43976
0.8496	Intermediate Similarity	NPC125361
0.8496	Intermediate Similarity	NPC128133
0.8496	Intermediate Similarity	NPC206618
0.8496	Intermediate Similarity	NPC51925
0.8496	Intermediate Similarity	NPC154085
0.8487	Intermediate Similarity	NPC233500
0.8482	Intermediate Similarity	NPC234160
0.8482	Intermediate Similarity	NPC33053
0.848	Intermediate Similarity	NPC329636
0.8475	Intermediate Similarity	NPC219656
0.8475	Intermediate Similarity	NPC477071
0.8475	Intermediate Similarity	NPC470914
0.8468	Intermediate Similarity	NPC470885
0.8468	Intermediate Similarity	NPC187400
0.8468	Intermediate Similarity	NPC221562
0.8468	Intermediate Similarity	NPC93352
0.8462	Intermediate Similarity	NPC100048
0.8462	Intermediate Similarity	NPC20979
0.8462	Intermediate Similarity	NPC477807
0.8462	Intermediate Similarity	NPC476690
0.8455	Intermediate Similarity	NPC471407
0.8455	Intermediate Similarity	NPC9499
0.8455	Intermediate Similarity	NPC86159
0.8455	Intermediate Similarity	NPC180079
0.8455	Intermediate Similarity	NPC471358
0.8455	Intermediate Similarity	NPC89514
0.8455	Intermediate Similarity	NPC471361
0.8455	Intermediate Similarity	NPC471359
0.8455	Intermediate Similarity	NPC471360
0.8455	Intermediate Similarity	NPC469753
0.8455	Intermediate Similarity	NPC469751
0.8455	Intermediate Similarity	NPC10823
0.8455	Intermediate Similarity	NPC284406
0.8455	Intermediate Similarity	NPC17896
0.8455	Intermediate Similarity	NPC251866
0.8455	Intermediate Similarity	NPC219085
0.8455	Intermediate Similarity	NPC70542
0.8455	Intermediate Similarity	NPC6108

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC81222 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	1839
0.2-0.3	4080
0.3-0.4	2024
0.4-0.5	527
0.5-0.6	277
0.6-0.7	153
0.7-0.8	17
0.8-0.85	0
0.85-0.9	2
0.9-0.95	11
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9643	High Similarity	NPD8033	Approved
0.9381	High Similarity	NPD8377	Approved
0.9381	High Similarity	NPD8294	Approved
0.9298	High Similarity	NPD8378	Approved
0.9298	High Similarity	NPD8380	Approved
0.9298	High Similarity	NPD8335	Approved
0.9298	High Similarity	NPD8296	Approved
0.9298	High Similarity	NPD8379	Approved
0.9204	High Similarity	NPD7327	Approved
0.9204	High Similarity	NPD7328	Approved
0.9123	High Similarity	NPD7516	Approved
0.8803	High Similarity	NPD7503	Approved
0.8667	High Similarity	NPD7507	Approved
0.8455	Intermediate Similarity	NPD7319	Approved
0.7931	Intermediate Similarity	NPD6686	Approved
0.7899	Intermediate Similarity	NPD8133	Approved
0.7845	Intermediate Similarity	NPD6412	Phase 2
0.7609	Intermediate Similarity	NPD7625	Phase 1
0.7544	Intermediate Similarity	NPD7638	Approved
0.7519	Intermediate Similarity	NPD7736	Approved
0.7478	Intermediate Similarity	NPD7639	Approved
0.7478	Intermediate Similarity	NPD7640	Approved
0.7442	Intermediate Similarity	NPD8293	Discontinued
0.7402	Intermediate Similarity	NPD6370	Approved
0.7344	Intermediate Similarity	NPD8328	Phase 3
0.7287	Intermediate Similarity	NPD7492	Approved
0.728	Intermediate Similarity	NPD7115	Discovery
0.7273	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6054	Approved
0.7244	Intermediate Similarity	NPD6059	Approved
0.7236	Intermediate Similarity	NPD6882	Approved
0.7231	Intermediate Similarity	NPD6616	Approved
0.7188	Intermediate Similarity	NPD8513	Phase 3
0.7188	Intermediate Similarity	NPD8517	Approved
0.7188	Intermediate Similarity	NPD8516	Approved
0.7188	Intermediate Similarity	NPD8515	Approved
0.7176	Intermediate Similarity	NPD7078	Approved
0.7143	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6009	Approved
0.7131	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6319	Approved
0.7105	Intermediate Similarity	NPD8171	Discontinued
0.7097	Intermediate Similarity	NPD6053	Discontinued
0.7097	Intermediate Similarity	NPD8297	Approved
0.7073	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6015	Approved
0.7054	Intermediate Similarity	NPD6016	Approved
0.7049	Intermediate Similarity	NPD7320	Approved
0.704	Intermediate Similarity	NPD4632	Approved
0.7025	Intermediate Similarity	NPD5739	Approved
0.7025	Intermediate Similarity	NPD6402	Approved
0.7025	Intermediate Similarity	NPD7128	Approved
0.7025	Intermediate Similarity	NPD6008	Approved
0.7025	Intermediate Similarity	NPD6675	Approved
0.7	Intermediate Similarity	NPD5988	Approved
0.6992	Remote Similarity	NPD6373	Approved
0.6992	Remote Similarity	NPD6372	Approved
0.6991	Remote Similarity	NPD6051	Approved
0.6949	Remote Similarity	NPD4225	Approved
0.6947	Remote Similarity	NPD6067	Discontinued
0.6917	Remote Similarity	NPD7632	Discontinued
0.6912	Remote Similarity	NPD8449	Approved
0.6911	Remote Similarity	NPD6881	Approved
0.6911	Remote Similarity	NPD6899	Approved
0.688	Remote Similarity	NPD6650	Approved
0.688	Remote Similarity	NPD6649	Approved
0.6861	Remote Similarity	NPD8450	Suspended
0.6833	Remote Similarity	NPD5344	Discontinued
0.6829	Remote Similarity	NPD5701	Approved
0.6829	Remote Similarity	NPD5697	Approved
0.6829	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7290	Approved
0.68	Remote Similarity	NPD6883	Approved
0.68	Remote Similarity	NPD7102	Approved
0.6746	Remote Similarity	NPD6617	Approved
0.6746	Remote Similarity	NPD8130	Phase 1
0.6746	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6869	Approved
0.6746	Remote Similarity	NPD6847	Approved
0.6741	Remote Similarity	NPD6033	Approved
0.6723	Remote Similarity	NPD6084	Phase 2
0.6723	Remote Similarity	NPD6083	Phase 2
0.672	Remote Similarity	NPD6013	Approved
0.672	Remote Similarity	NPD6014	Approved
0.672	Remote Similarity	NPD6012	Approved
0.6696	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6011	Approved
0.6614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6648	Approved
0.661	Remote Similarity	NPD7748	Approved
0.6593	Remote Similarity	NPD6336	Discontinued
0.6583	Remote Similarity	NPD7902	Approved
0.6583	Remote Similarity	NPD4755	Approved
0.656	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5695	Phase 3
0.6555	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4634	Approved
0.6529	Remote Similarity	NPD5696	Approved
0.6525	Remote Similarity	NPD4202	Approved
0.6522	Remote Similarity	NPD7524	Approved
0.6522	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5211	Phase 2
0.6496	Remote Similarity	NPD46	Approved
0.6496	Remote Similarity	NPD6698	Approved
0.6486	Remote Similarity	NPD7525	Registered
0.6475	Remote Similarity	NPD5285	Approved
0.6475	Remote Similarity	NPD4700	Approved
0.6475	Remote Similarity	NPD5286	Approved
0.6475	Remote Similarity	NPD4696	Approved
0.6466	Remote Similarity	NPD6903	Approved
0.6466	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7515	Phase 2
0.6441	Remote Similarity	NPD5693	Phase 1
0.6435	Remote Similarity	NPD5330	Approved
0.6435	Remote Similarity	NPD7146	Approved
0.6435	Remote Similarity	NPD7521	Approved
0.6435	Remote Similarity	NPD7334	Approved
0.6435	Remote Similarity	NPD6409	Approved
0.6435	Remote Similarity	NPD6684	Approved
0.6423	Remote Similarity	NPD4159	Approved
0.6423	Remote Similarity	NPD8074	Phase 3
0.6412	Remote Similarity	NPD6274	Approved
0.6406	Remote Similarity	NPD6371	Approved
0.6404	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5141	Approved
0.6391	Remote Similarity	NPD7101	Approved
0.6391	Remote Similarity	NPD7100	Approved
0.6378	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD4633	Approved
0.6371	Remote Similarity	NPD5224	Approved
0.6371	Remote Similarity	NPD5225	Approved
0.6371	Remote Similarity	NPD5226	Approved
0.6356	Remote Similarity	NPD7838	Discovery
0.6349	Remote Similarity	NPD4768	Approved
0.6349	Remote Similarity	NPD4767	Approved
0.6339	Remote Similarity	NPD6928	Phase 2
0.6333	Remote Similarity	NPD7900	Approved
0.6333	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.632	Remote Similarity	NPD5174	Approved
0.632	Remote Similarity	NPD5175	Approved
0.6319	Remote Similarity	NPD7799	Discontinued
0.6316	Remote Similarity	NPD6335	Approved
0.6316	Remote Similarity	NPD6695	Phase 3
0.6303	Remote Similarity	NPD7637	Suspended
0.6303	Remote Similarity	NPD8034	Phase 2
0.6303	Remote Similarity	NPD8035	Phase 2
0.6296	Remote Similarity	NPD6908	Approved
0.6296	Remote Similarity	NPD6909	Approved
0.629	Remote Similarity	NPD5223	Approved
0.6286	Remote Similarity	NPD5956	Approved
0.6273	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD4753	Phase 2
0.6271	Remote Similarity	NPD5328	Approved
0.6271	Remote Similarity	NPD6080	Approved
0.6271	Remote Similarity	NPD6904	Approved
0.6271	Remote Similarity	NPD6673	Approved
0.6259	Remote Similarity	NPD8337	Approved
0.6259	Remote Similarity	NPD8336	Approved
0.625	Remote Similarity	NPD7645	Phase 2
0.625	Remote Similarity	NPD4729	Approved
0.625	Remote Similarity	NPD4195	Approved
0.625	Remote Similarity	NPD4730	Approved
0.6241	Remote Similarity	NPD6317	Approved
0.6241	Remote Similarity	NPD7260	Phase 2
0.6198	Remote Similarity	NPD6001	Approved
0.6194	Remote Similarity	NPD6314	Approved
0.6194	Remote Similarity	NPD6313	Approved
0.619	Remote Similarity	NPD4754	Approved
0.6186	Remote Similarity	NPD6672	Approved
0.6186	Remote Similarity	NPD5737	Approved
0.6182	Remote Similarity	NPD7339	Approved
0.6182	Remote Similarity	NPD6942	Approved
0.6176	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD5284	Approved
0.6167	Remote Similarity	NPD5281	Approved
0.6167	Remote Similarity	NPD6079	Approved
0.6154	Remote Similarity	NPD5248	Approved
0.6154	Remote Similarity	NPD5249	Phase 3
0.6154	Remote Similarity	NPD3618	Phase 1
0.6154	Remote Similarity	NPD5250	Approved
0.6154	Remote Similarity	NPD5251	Approved
0.6154	Remote Similarity	NPD5247	Approved
0.6124	Remote Similarity	NPD5128	Approved
0.6121	Remote Similarity	NPD3665	Phase 1
0.6121	Remote Similarity	NPD4786	Approved
0.6121	Remote Similarity	NPD3133	Approved
0.6121	Remote Similarity	NPD3666	Approved
0.6102	Remote Similarity	NPD4251	Approved
0.6102	Remote Similarity	NPD7750	Discontinued
0.6102	Remote Similarity	NPD4250	Approved
0.6091	Remote Similarity	NPD4784	Approved
0.6091	Remote Similarity	NPD4785	Approved
0.6087	Remote Similarity	NPD4223	Phase 3
0.6087	Remote Similarity	NPD4221	Approved
0.6087	Remote Similarity	NPD4752	Clinical (unspecified phase)

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