NPASS Compound

Structure

NPC265127 OpenBabel07101718232D 40 44 0 0 1 0 0 0 0 0999 V2000 4.8973 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2500 5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2793 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9703 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 -1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -2.8660 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 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 3.9192 5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6102 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9921 2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7709 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 1 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 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6320 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3230 3.0032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 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 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7709 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9629 4.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3448 2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 2 0 0 0 0 5 20 1 0 0 0 0 6 29 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 32 1 0 0 0 0 13 14 1 0 0 0 0 13 29 1 0 0 0 0 15 21 1 0 0 0 0 15 30 1 0 0 0 0 16 32 1 0 0 0 0 16 33 1 0 0 0 0 17 18 1 0 0 0 0 18 26 1 0 0 0 0 19 4 1 1 0 0 0 19 25 1 0 0 0 0 19 27 1 0 0 0 0 20 34 2 0 0 0 0 20 40 1 0 0 0 0 21 25 1 0 0 0 0 21 40 1 1 0 0 0 22 30 1 6 0 0 0 22 33 1 0 0 0 0 23 31 1 1 0 0 0 23 32 1 0 0 0 0 24 31 1 1 0 0 0 24 35 1 0 0 0 0 25 29 1 1 0 0 0 26 27 1 0 0 0 0 26 36 2 0 0 0 0 27 37 1 1 0 0 0 28 31 1 0 0 0 0 28 38 2 0 0 0 0 28 39 1 0 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 31 8 1 1 0 0 0 32 33 1 6 0 0 0 33 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	558.36
Volume:	587.527
LogP:	3.865
LogD:	2.981
LogS:	-4.35
# Rotatable Bonds:	8
TPSA:	117.97
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	6.045
Fsp3:	0.879
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.448
MDCK Permeability:	1.901135874504689e-05
Pgp-inhibitor:	0.88
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.92

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.279
Plasma Protein Binding (PPB):	96.34579467773438%
Volume Distribution (VD):	0.535
Pgp-substrate:	3.4991915225982666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.336
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.816
CYP2C9-inhibitor:	0.081
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.485
CYP3A4-substrate:	0.597

ADMET: Excretion

Clearance (CL):	3.105
Half-life (T1/2):	0.264

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.33
Drug-inuced Liver Injury (DILI):	0.306
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.641
Maximum Recommended Daily Dose:	0.59
Skin Sensitization:	0.281
Carcinogencity:	0.534
Eye Corrosion:	0.004
Eye Irritation:	0.011
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: NPC265127

Natural Product ID:	NPC265127
*Common Name:**	MFGGXMSNGODHMJ-AEHIQNLVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MFGGXMSNGODHMJ-AEHIQNLVSA-N
Standard InCHI:	InChI=1S/C33H50O7/c1-17(2)18(3)26(36)27(37)19(4)25-21(40-20(5)34)15-30(7)22-9-10-23-31(8,28(38)39)24(35)11-12-32(23)16-33(22,32)14-13-29(25,30)6/h17,19,21-25,27,35,37H,3,9-16H2,1-2,4-8H3,(H,38,39)/t19-,21-,22-,23-,24-,25-,27+,29+,30-,31-,32+,33-/m0/s1
SMILES:	CC(C)C(=C)C(=O)[C@@H]([C@@H](C)[C@H]1[C@H](C[C@@]2(C)[C@@H]3CC[C@H]4[C@@](C)([C@H](CC[C@]54C[C@@]35CC[C@]12C)O)C(=O)O)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1951411
PubChem CID:	57332644
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22168134]
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22206869]
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	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
Others	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	FC	=	1.8	n.a.	PMID[543232]
NPT2	Others	Unspecified	FC	=	1.3	n.a.	PMID[543232]
NPT2	Others	Unspecified	FC	=	1.2	n.a.	PMID[543232]

☑ 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 NPC265127 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	250
0.1-0.2	1822
0.2-0.3	6384
0.3-0.4	12524
0.4-0.5	8284
0.5-0.6	6076
0.6-0.7	5394
0.7-0.8	1735
0.8-0.85	183
0.85-0.9	40
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC211224
0.9592	High Similarity	NPC470310
0.932	High Similarity	NPC470281
0.91	High Similarity	NPC15396
0.898	High Similarity	NPC13949
0.8922	High Similarity	NPC310586
0.8878	High Similarity	NPC210214
0.8824	High Similarity	NPC87927
0.8812	High Similarity	NPC289148
0.8812	High Similarity	NPC52899
0.8812	High Similarity	NPC163963
0.8788	High Similarity	NPC234564
0.8725	High Similarity	NPC76866
0.8725	High Similarity	NPC214946
0.8725	High Similarity	NPC304832
0.8725	High Similarity	NPC246736
0.8725	High Similarity	NPC148628
0.8725	High Similarity	NPC286519
0.8725	High Similarity	NPC88203
0.8713	High Similarity	NPC94906
0.8713	High Similarity	NPC287676
0.8692	High Similarity	NPC71348
0.8687	High Similarity	NPC205173
0.8687	High Similarity	NPC266431
0.8673	High Similarity	NPC294263
0.8654	High Similarity	NPC181265
0.8641	High Similarity	NPC469985
0.8627	High Similarity	NPC71706
0.8627	High Similarity	NPC46848
0.8627	High Similarity	NPC75941
0.8614	High Similarity	NPC16911
0.8614	High Similarity	NPC472028
0.8614	High Similarity	NPC78427
0.8614	High Similarity	NPC471038
0.8614	High Similarity	NPC474793
0.8611	High Similarity	NPC202889
0.86	High Similarity	NPC329910
0.8586	High Similarity	NPC169751
0.8586	High Similarity	NPC272635
0.8571	High Similarity	NPC201908
0.8571	High Similarity	NPC176949
0.8571	High Similarity	NPC250753
0.8558	High Similarity	NPC235889
0.8558	High Similarity	NPC98603
0.8544	High Similarity	NPC275990
0.8544	High Similarity	NPC124544
0.85	High Similarity	NPC470232
0.85	High Similarity	NPC470229
0.85	High Similarity	NPC263135
0.85	High Similarity	NPC98639
0.85	High Similarity	NPC288906
0.8491	Intermediate Similarity	NPC94529
0.8491	Intermediate Similarity	NPC218123
0.8491	Intermediate Similarity	NPC112895
0.8491	Intermediate Similarity	NPC231278
0.8485	Intermediate Similarity	NPC471902
0.8485	Intermediate Similarity	NPC473690
0.8485	Intermediate Similarity	NPC287118
0.8485	Intermediate Similarity	NPC59170
0.8476	Intermediate Similarity	NPC37600
0.8469	Intermediate Similarity	NPC180849
0.8462	Intermediate Similarity	NPC216114
0.8455	Intermediate Similarity	NPC270958
0.8454	Intermediate Similarity	NPC146937
0.8447	Intermediate Similarity	NPC236585
0.8431	Intermediate Similarity	NPC38471
0.8431	Intermediate Similarity	NPC20479
0.8431	Intermediate Similarity	NPC98837
0.8431	Intermediate Similarity	NPC38296
0.8431	Intermediate Similarity	NPC162459
0.8431	Intermediate Similarity	NPC28864
0.8416	Intermediate Similarity	NPC29410
0.8416	Intermediate Similarity	NPC200054
0.8416	Intermediate Similarity	NPC327788
0.8411	Intermediate Similarity	NPC258543
0.8411	Intermediate Similarity	NPC241927
0.84	Intermediate Similarity	NPC47853
0.84	Intermediate Similarity	NPC475118
0.84	Intermediate Similarity	NPC470386
0.84	Intermediate Similarity	NPC470385
0.8396	Intermediate Similarity	NPC44063
0.8384	Intermediate Similarity	NPC211403
0.8384	Intermediate Similarity	NPC471901
0.8384	Intermediate Similarity	NPC475416
0.8384	Intermediate Similarity	NPC198242
0.8381	Intermediate Similarity	NPC84928
0.8381	Intermediate Similarity	NPC47281
0.8365	Intermediate Similarity	NPC193934
0.8365	Intermediate Similarity	NPC271980
0.8351	Intermediate Similarity	NPC134197
0.835	Intermediate Similarity	NPC41971
0.835	Intermediate Similarity	NPC37047
0.835	Intermediate Similarity	NPC180733
0.835	Intermediate Similarity	NPC108371
0.835	Intermediate Similarity	NPC293866
0.8333	Intermediate Similarity	NPC10864
0.8318	Intermediate Similarity	NPC273155
0.8317	Intermediate Similarity	NPC138245
0.8317	Intermediate Similarity	NPC29112
0.8317	Intermediate Similarity	NPC84018
0.8317	Intermediate Similarity	NPC231060
0.8304	Intermediate Similarity	NPC118638
0.8302	Intermediate Similarity	NPC50535
0.8302	Intermediate Similarity	NPC278628
0.8302	Intermediate Similarity	NPC231530
0.8302	Intermediate Similarity	NPC295366
0.8302	Intermediate Similarity	NPC200957
0.8302	Intermediate Similarity	NPC28791
0.8302	Intermediate Similarity	NPC138908
0.83	Intermediate Similarity	NPC144739
0.83	Intermediate Similarity	NPC59350
0.83	Intermediate Similarity	NPC181594
0.8286	Intermediate Similarity	NPC139347
0.8286	Intermediate Similarity	NPC277074
0.8286	Intermediate Similarity	NPC122811
0.8286	Intermediate Similarity	NPC312900
0.8286	Intermediate Similarity	NPC209298
0.8269	Intermediate Similarity	NPC121218
0.8269	Intermediate Similarity	NPC471790
0.8269	Intermediate Similarity	NPC253886
0.8269	Intermediate Similarity	NPC148279
0.8269	Intermediate Similarity	NPC60947
0.8257	Intermediate Similarity	NPC231589
0.8257	Intermediate Similarity	NPC118860
0.8257	Intermediate Similarity	NPC329953
0.8257	Intermediate Similarity	NPC214797
0.8252	Intermediate Similarity	NPC288
0.8252	Intermediate Similarity	NPC109059
0.8252	Intermediate Similarity	NPC89099
0.8241	Intermediate Similarity	NPC2766
0.8235	Intermediate Similarity	NPC104568
0.8235	Intermediate Similarity	NPC219353
0.8235	Intermediate Similarity	NPC470387
0.8224	Intermediate Similarity	NPC86852
0.8224	Intermediate Similarity	NPC470952
0.8224	Intermediate Similarity	NPC166993
0.8224	Intermediate Similarity	NPC220974
0.8224	Intermediate Similarity	NPC251824
0.8218	Intermediate Similarity	NPC191094
0.8218	Intermediate Similarity	NPC292374
0.8218	Intermediate Similarity	NPC111524
0.8218	Intermediate Similarity	NPC104371
0.8218	Intermediate Similarity	NPC91772
0.8218	Intermediate Similarity	NPC101233
0.8218	Intermediate Similarity	NPC129004
0.8218	Intermediate Similarity	NPC261333
0.8218	Intermediate Similarity	NPC215271
0.8218	Intermediate Similarity	NPC302008
0.8218	Intermediate Similarity	NPC153775
0.8218	Intermediate Similarity	NPC29247
0.8218	Intermediate Similarity	NPC289539
0.8208	Intermediate Similarity	NPC96268
0.8208	Intermediate Similarity	NPC474558
0.8208	Intermediate Similarity	NPC13149
0.8208	Intermediate Similarity	NPC29705
0.8208	Intermediate Similarity	NPC202793
0.82	Intermediate Similarity	NPC476168
0.82	Intermediate Similarity	NPC299185
0.82	Intermediate Similarity	NPC278106
0.82	Intermediate Similarity	NPC470230
0.8198	Intermediate Similarity	NPC300051
0.819	Intermediate Similarity	NPC271266
0.819	Intermediate Similarity	NPC309388
0.819	Intermediate Similarity	NPC170615
0.819	Intermediate Similarity	NPC308351
0.819	Intermediate Similarity	NPC475803
0.8182	Intermediate Similarity	NPC213832
0.8182	Intermediate Similarity	NPC170487
0.8182	Intermediate Similarity	NPC57954
0.8182	Intermediate Similarity	NPC476163
0.8173	Intermediate Similarity	NPC156324
0.8173	Intermediate Similarity	NPC55503
0.8173	Intermediate Similarity	NPC470388
0.8173	Intermediate Similarity	NPC293890
0.8165	Intermediate Similarity	NPC197428
0.8165	Intermediate Similarity	NPC471093
0.8163	Intermediate Similarity	NPC165895
0.8163	Intermediate Similarity	NPC174619
0.8155	Intermediate Similarity	NPC469810
0.8155	Intermediate Similarity	NPC253586
0.8144	Intermediate Similarity	NPC76518
0.8137	Intermediate Similarity	NPC470031
0.8131	Intermediate Similarity	NPC4115
0.8113	Intermediate Similarity	NPC96217
0.8113	Intermediate Similarity	NPC159442
0.8108	Intermediate Similarity	NPC73986
0.8108	Intermediate Similarity	NPC52634
0.8108	Intermediate Similarity	NPC471252
0.81	Intermediate Similarity	NPC261994
0.81	Intermediate Similarity	NPC80401
0.81	Intermediate Similarity	NPC470378
0.81	Intermediate Similarity	NPC149761
0.8095	Intermediate Similarity	NPC473514
0.8095	Intermediate Similarity	NPC252614
0.8091	Intermediate Similarity	NPC94650
0.8091	Intermediate Similarity	NPC43775
0.8091	Intermediate Similarity	NPC29505
0.8091	Intermediate Similarity	NPC470311
0.8081	Intermediate Similarity	NPC56413
0.8081	Intermediate Similarity	NPC471900

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 NPC265127 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	2191
0.2-0.3	4003
0.3-0.4	1784
0.4-0.5	468
0.5-0.6	202
0.6-0.7	132
0.7-0.8	103
0.8-0.85	21
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8491	Intermediate Similarity	NPD6881	Approved
0.8491	Intermediate Similarity	NPD6899	Approved
0.8476	Intermediate Similarity	NPD6675	Approved
0.8476	Intermediate Similarity	NPD6402	Approved
0.8476	Intermediate Similarity	NPD5739	Approved
0.8476	Intermediate Similarity	NPD7128	Approved
0.8426	Intermediate Similarity	NPD8130	Phase 1
0.8396	Intermediate Similarity	NPD5697	Approved
0.8349	Intermediate Similarity	NPD8297	Approved
0.8333	Intermediate Similarity	NPD7290	Approved
0.8333	Intermediate Similarity	NPD6883	Approved
0.8333	Intermediate Similarity	NPD7102	Approved
0.8318	Intermediate Similarity	NPD7320	Approved
0.8257	Intermediate Similarity	NPD6617	Approved
0.8257	Intermediate Similarity	NPD6869	Approved
0.8257	Intermediate Similarity	NPD6649	Approved
0.8257	Intermediate Similarity	NPD6650	Approved
0.8257	Intermediate Similarity	NPD6847	Approved
0.8241	Intermediate Similarity	NPD6013	Approved
0.8241	Intermediate Similarity	NPD6014	Approved
0.8241	Intermediate Similarity	NPD6373	Approved
0.8241	Intermediate Similarity	NPD6012	Approved
0.8241	Intermediate Similarity	NPD6372	Approved
0.8224	Intermediate Similarity	NPD5701	Approved
0.8182	Intermediate Similarity	NPD6882	Approved
0.8148	Intermediate Similarity	NPD6011	Approved
0.802	Intermediate Similarity	NPD8034	Phase 2
0.802	Intermediate Similarity	NPD8035	Phase 2
0.8	Intermediate Similarity	NPD5286	Approved
0.8	Intermediate Similarity	NPD4696	Approved
0.8	Intermediate Similarity	NPD5285	Approved
0.7981	Intermediate Similarity	NPD4755	Approved
0.7928	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD5225	Approved
0.785	Intermediate Similarity	NPD5226	Approved
0.785	Intermediate Similarity	NPD4633	Approved
0.785	Intermediate Similarity	NPD5224	Approved
0.785	Intermediate Similarity	NPD5211	Phase 2
0.7845	Intermediate Similarity	NPD6319	Approved
0.7833	Intermediate Similarity	NPD7736	Approved
0.783	Intermediate Similarity	NPD4700	Approved
0.781	Intermediate Similarity	NPD6084	Phase 2
0.781	Intermediate Similarity	NPD6083	Phase 2
0.7807	Intermediate Similarity	NPD6274	Approved
0.7778	Intermediate Similarity	NPD5174	Approved
0.7778	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5175	Approved
0.7759	Intermediate Similarity	NPD7100	Approved
0.7759	Intermediate Similarity	NPD7101	Approved
0.7757	Intermediate Similarity	NPD5223	Approved
0.7731	Intermediate Similarity	NPD7492	Approved
0.7706	Intermediate Similarity	NPD5141	Approved
0.7692	Intermediate Similarity	NPD6054	Approved
0.7679	Intermediate Similarity	NPD4634	Approved
0.7672	Intermediate Similarity	NPD6335	Approved
0.7667	Intermediate Similarity	NPD6616	Approved
0.7647	Intermediate Similarity	NPD7604	Phase 2
0.7632	Intermediate Similarity	NPD4632	Approved
0.7603	Intermediate Similarity	NPD8293	Discontinued
0.7603	Intermediate Similarity	NPD7078	Approved
0.7596	Intermediate Similarity	NPD6399	Phase 3
0.7586	Intermediate Similarity	NPD6317	Approved
0.7576	Intermediate Similarity	NPD4788	Approved
0.7563	Intermediate Similarity	NPD6370	Approved
0.7547	Intermediate Similarity	NPD5222	Approved
0.7547	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5221	Approved
0.7542	Intermediate Similarity	NPD6059	Approved
0.7521	Intermediate Similarity	NPD6313	Approved
0.7521	Intermediate Similarity	NPD6314	Approved
0.75	Intermediate Similarity	NPD4730	Approved
0.75	Intermediate Similarity	NPD5128	Approved
0.75	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD4729	Approved
0.7479	Intermediate Similarity	NPD6908	Approved
0.7479	Intermediate Similarity	NPD6015	Approved
0.7479	Intermediate Similarity	NPD6016	Approved
0.7479	Intermediate Similarity	NPD6909	Approved
0.7477	Intermediate Similarity	NPD4768	Approved
0.7477	Intermediate Similarity	NPD5173	Approved
0.7477	Intermediate Similarity	NPD4767	Approved
0.7477	Intermediate Similarity	NPD6008	Approved
0.7476	Intermediate Similarity	NPD5328	Approved
0.7455	Intermediate Similarity	NPD4754	Approved
0.7453	Intermediate Similarity	NPD5695	Phase 3
0.7436	Intermediate Similarity	NPD7115	Discovery
0.7436	Intermediate Similarity	NPD6009	Approved
0.7417	Intermediate Similarity	NPD5988	Approved
0.7407	Intermediate Similarity	NPD5696	Approved
0.7383	Intermediate Similarity	NPD4697	Phase 3
0.7368	Intermediate Similarity	NPD5247	Approved
0.7368	Intermediate Similarity	NPD5249	Phase 3
0.7368	Intermediate Similarity	NPD5251	Approved
0.7368	Intermediate Similarity	NPD5250	Approved
0.7368	Intermediate Similarity	NPD5248	Approved
0.7358	Intermediate Similarity	NPD7748	Approved
0.735	Intermediate Similarity	NPD6868	Approved
0.7333	Intermediate Similarity	NPD5983	Phase 2
0.7333	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6116	Phase 1
0.7315	Intermediate Similarity	NPD7902	Approved
0.7308	Intermediate Similarity	NPD4753	Phase 2
0.7304	Intermediate Similarity	NPD5216	Approved
0.7304	Intermediate Similarity	NPD5217	Approved
0.7304	Intermediate Similarity	NPD5215	Approved
0.729	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD4202	Approved
0.7248	Intermediate Similarity	NPD7638	Approved
0.7236	Intermediate Similarity	NPD6336	Discontinued
0.7217	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5135	Approved
0.7217	Intermediate Similarity	NPD5169	Approved
0.7216	Intermediate Similarity	NPD6117	Approved
0.7212	Intermediate Similarity	NPD5737	Approved
0.7212	Intermediate Similarity	NPD6672	Approved
0.7212	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6409	Approved
0.7184	Intermediate Similarity	NPD7521	Approved
0.7184	Intermediate Similarity	NPD7334	Approved
0.7184	Intermediate Similarity	NPD6684	Approved
0.7184	Intermediate Similarity	NPD7146	Approved
0.7184	Intermediate Similarity	NPD5330	Approved
0.7182	Intermediate Similarity	NPD7640	Approved
0.7182	Intermediate Similarity	NPD7639	Approved
0.717	Intermediate Similarity	NPD7515	Phase 2
0.7157	Intermediate Similarity	NPD4786	Approved
0.7155	Intermediate Similarity	NPD5127	Approved
0.7143	Intermediate Similarity	NPD6673	Approved
0.7143	Intermediate Similarity	NPD6904	Approved
0.7143	Intermediate Similarity	NPD6080	Approved
0.713	Intermediate Similarity	NPD4629	Approved
0.713	Intermediate Similarity	NPD5210	Approved
0.7073	Intermediate Similarity	NPD8328	Phase 3
0.7071	Intermediate Similarity	NPD6118	Approved
0.7071	Intermediate Similarity	NPD6114	Approved
0.7071	Intermediate Similarity	NPD6697	Approved
0.7071	Intermediate Similarity	NPD6115	Approved
0.7063	Intermediate Similarity	NPD7319	Approved
0.7048	Intermediate Similarity	NPD6903	Approved
0.7037	Intermediate Similarity	NPD7900	Approved
0.7037	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6098	Approved
0.7019	Intermediate Similarity	NPD3618	Phase 1
0.701	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6411	Approved
0.7	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.699	Remote Similarity	NPD3133	Approved
0.699	Remote Similarity	NPD3666	Approved
0.699	Remote Similarity	NPD3665	Phase 1
0.6984	Remote Similarity	NPD6033	Approved
0.6975	Remote Similarity	NPD5167	Approved
0.6961	Remote Similarity	NPD3667	Approved
0.696	Remote Similarity	NPD7507	Approved
0.6923	Remote Similarity	NPD5329	Approved
0.6897	Remote Similarity	NPD5168	Approved
0.6891	Remote Similarity	NPD8133	Approved
0.6881	Remote Similarity	NPD6001	Approved
0.6857	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6050	Approved
0.6852	Remote Similarity	NPD5693	Phase 1
0.6827	Remote Similarity	NPD4197	Approved
0.6822	Remote Similarity	NPD6101	Approved
0.6822	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6412	Phase 2
0.6804	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5777	Approved
0.6804	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6435	Approved
0.6786	Remote Similarity	NPD4225	Approved
0.6768	Remote Similarity	NPD3702	Approved
0.6768	Remote Similarity	NPD3703	Phase 2
0.6767	Remote Similarity	NPD6333	Approved
0.6767	Remote Similarity	NPD6334	Approved
0.6765	Remote Similarity	NPD7525	Registered
0.6759	Remote Similarity	NPD5692	Phase 3
0.6754	Remote Similarity	NPD7632	Discontinued
0.6701	Remote Similarity	NPD4244	Approved
0.6701	Remote Similarity	NPD4245	Approved
0.6701	Remote Similarity	NPD4789	Approved
0.6698	Remote Similarity	NPD5690	Phase 2
0.6698	Remote Similarity	NPD5279	Phase 3
0.6697	Remote Similarity	NPD5281	Approved
0.6697	Remote Similarity	NPD5694	Approved
0.6697	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD1700	Approved
0.6638	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD3573	Approved
0.6635	Remote Similarity	NPD4221	Approved
0.6635	Remote Similarity	NPD4223	Phase 3
0.6606	Remote Similarity	NPD5785	Approved
0.6602	Remote Similarity	NPD5368	Approved
0.6598	Remote Similarity	NPD3698	Phase 2
0.6598	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5208	Approved
0.6549	Remote Similarity	NPD5959	Approved
0.6545	Remote Similarity	NPD7637	Suspended
0.6542	Remote Similarity	NPD5280	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