NPASS Compound

Structure

CID267921 OpenBabel06191716072D 26 30 0 0 1 0 0 0 0 0999 V2000 3.0115 -2.0033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9260 -2.1451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6018 -2.7745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3906 -2.3191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8130 -2.3190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8131 -3.2858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6261 -1.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0675 -0.7987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8130 -0.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0955 -2.0033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6261 -2.8164 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0001 -2.8164 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.8776 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6018 -0.9528 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7518 -1.4081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7912 -0.0618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8130 -0.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3906 -1.4082 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8130 -1.4082 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8130 -1.4081 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7932 -3.2744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2098 -0.6148 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1817 0.6151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6018 -0.0139 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6971 0.0334 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 10 2 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 18 1 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 8 18 1 0 0 0 0 8 25 1 0 0 0 0 9 19 1 0 0 0 0 9 26 1 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 6 1 6 0 0 0 12 13 1 0 0 0 0 12 21 1 1 0 0 0 13 19 1 1 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 18 1 1 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 15 22 2 0 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 24 2 0 0 0 0 17 26 1 0 0 0 0 18 2 1 6 0 0 0 19 5 1 1 0 0 0 20 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.16
Volume:	353.889
LogP:	1.505
LogD:	1.26
LogS:	-3.915
# Rotatable Bonds:	0
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.399
Synthetic Accessibility Score:	6.551
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.323
MDCK Permeability:	1.8189546608482487e-05
Pgp-inhibitor:	0.292
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.874
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.795
Plasma Protein Binding (PPB):	45.75727081298828%
Volume Distribution (VD):	0.742
Pgp-substrate:	63.60198211669922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.883
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.749
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.925
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	3.566
Half-life (T1/2):	0.13

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.184
AMES Toxicity:	0.272
Rat Oral Acute Toxicity:	0.314
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.25
Carcinogencity:	0.683
Eye Corrosion:	0.004
Eye Irritation:	0.164
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC267921

Natural Product ID:	NPC267921
*Common Name:**	Ludongnin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HXTZXDWMLRAQTL-VWGMWKOWSA-N
Standard InCHI:	InChI=1S/C20H24O6/c1-10-11-6-12(21)13-19(9-26-17(24)20(13,7-11)15(10)22)5-3-4-18(2)8-25-16(23)14(18)19/h11-14,21H,1,3-9H2,2H3/t11-,12-,13+,14-,18+,19-,20+/m1/s1
SMILES:	C=C1[C@@H]2C[C@H]([C@@H]3[C@](C1=O)(C2)C(=O)OC[C@@]13CCC[C@@]2([C@H]1C(=O)OC2)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463923
PubChem CID:	9975782
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14575445]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20521771]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28626.2	Isodon rubescens var. lushiensis	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	0.25	ug.mL-1	PMID[506734]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3100.0	nM	PMID[506735]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[506735]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[506735]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	10000.0	nM	PMID[506735]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	10000.0	nM	PMID[506735]

☑ 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 NPC267921 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	234
0.1-0.2	1687
0.2-0.3	6197
0.3-0.4	11031
0.4-0.5	9539
0.5-0.6	6203
0.6-0.7	5850
0.7-0.8	1654
0.8-0.85	174
0.85-0.9	71
0.9-0.95	54
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9485	High Similarity	NPC103172
0.9485	High Similarity	NPC164600
0.9468	High Similarity	NPC26270
0.9388	High Similarity	NPC96333
0.9388	High Similarity	NPC88833
0.9278	High Similarity	NPC96217
0.9271	High Similarity	NPC236585
0.9271	High Similarity	NPC148279
0.9263	High Similarity	NPC471038
0.9263	High Similarity	NPC474793
0.9192	High Similarity	NPC61071
0.9184	High Similarity	NPC101842
0.9149	High Similarity	NPC470232
0.9109	High Similarity	NPC98069
0.9109	High Similarity	NPC49730
0.9082	High Similarity	NPC139347
0.9072	High Similarity	NPC39683
0.9072	High Similarity	NPC46848
0.9053	High Similarity	NPC200054
0.9053	High Similarity	NPC329910
0.9053	High Similarity	NPC29410
0.9043	High Similarity	NPC475118
0.9043	High Similarity	NPC470386
0.9043	High Similarity	NPC470385
0.9032	High Similarity	NPC250753
0.898	High Similarity	NPC275990
0.8969	High Similarity	NPC470388
0.8947	High Similarity	NPC470229
0.8947	High Similarity	NPC98639
0.8913	High Similarity	NPC56413
0.8911	High Similarity	NPC232133
0.8889	High Similarity	NPC277074
0.8889	High Similarity	NPC122811
0.8889	High Similarity	NPC87927
0.8889	High Similarity	NPC209298
0.8878	High Similarity	NPC289148
0.8878	High Similarity	NPC52899
0.8878	High Similarity	NPC14634
0.8878	High Similarity	NPC163963
0.8866	High Similarity	NPC20479
0.8866	High Similarity	NPC89099
0.8866	High Similarity	NPC38296
0.8866	High Similarity	NPC98837
0.8866	High Similarity	NPC38471
0.8866	High Similarity	NPC28864
0.8866	High Similarity	NPC162459
0.8854	High Similarity	NPC470387
0.8842	High Similarity	NPC47853
0.883	High Similarity	NPC211403
0.883	High Similarity	NPC198242
0.8824	High Similarity	NPC469983
0.8817	High Similarity	NPC200580
0.8812	High Similarity	NPC471474
0.8812	High Similarity	NPC186054
0.88	High Similarity	NPC474558
0.88	High Similarity	NPC202793
0.88	High Similarity	NPC13149
0.8788	High Similarity	NPC88203
0.8788	High Similarity	NPC246736
0.8788	High Similarity	NPC148628
0.8788	High Similarity	NPC286519
0.8788	High Similarity	NPC304832
0.8788	High Similarity	NPC76866
0.8788	High Similarity	NPC214946
0.8776	High Similarity	NPC293866
0.8776	High Similarity	NPC287676
0.8763	High Similarity	NPC96839
0.8763	High Similarity	NPC10864
0.8725	High Similarity	NPC473410
0.8725	High Similarity	NPC471094
0.8725	High Similarity	NPC469984
0.8725	High Similarity	NPC63841
0.8713	High Similarity	NPC56656
0.8713	High Similarity	NPC200957
0.8713	High Similarity	NPC138908
0.87	High Similarity	NPC159442
0.87	High Similarity	NPC216114
0.8687	High Similarity	NPC252614
0.8673	High Similarity	NPC78427
0.8673	High Similarity	NPC16911
0.866	High Similarity	NPC13949
0.8632	High Similarity	NPC470230
0.8627	High Similarity	NPC176949
0.8627	High Similarity	NPC201908
0.8627	High Similarity	NPC166993
0.8614	High Similarity	NPC98603
0.8614	High Similarity	NPC96268
0.8614	High Similarity	NPC244247
0.8614	High Similarity	NPC84928
0.86	High Similarity	NPC475803
0.86	High Similarity	NPC309388
0.8571	High Similarity	NPC253586
0.8558	High Similarity	NPC471093
0.8558	High Similarity	NPC320383
0.8558	High Similarity	NPC137104
0.8558	High Similarity	NPC85391
0.8558	High Similarity	NPC474786
0.8544	High Similarity	NPC112895
0.8544	High Similarity	NPC218123
0.8544	High Similarity	NPC231278
0.8544	High Similarity	NPC273155
0.8542	High Similarity	NPC294263
0.8529	High Similarity	NPC285927
0.8529	High Similarity	NPC130511
0.8529	High Similarity	NPC307660
0.8526	High Similarity	NPC80401
0.8515	High Similarity	NPC140723
0.85	High Similarity	NPC471790
0.8485	Intermediate Similarity	NPC109059
0.8485	Intermediate Similarity	NPC288
0.8476	Intermediate Similarity	NPC213320
0.8476	Intermediate Similarity	NPC29505
0.8476	Intermediate Similarity	NPC329953
0.8462	Intermediate Similarity	NPC274827
0.8462	Intermediate Similarity	NPC131903
0.8462	Intermediate Similarity	NPC102741
0.8454	Intermediate Similarity	NPC191094
0.8454	Intermediate Similarity	NPC302008
0.8454	Intermediate Similarity	NPC41649
0.8447	Intermediate Similarity	NPC469746
0.8438	Intermediate Similarity	NPC476168
0.8431	Intermediate Similarity	NPC301787
0.8421	Intermediate Similarity	NPC471043
0.8416	Intermediate Similarity	NPC124544
0.8404	Intermediate Similarity	NPC259009
0.8404	Intermediate Similarity	NPC153604
0.84	Intermediate Similarity	NPC108371
0.8396	Intermediate Similarity	NPC473352
0.8396	Intermediate Similarity	NPC473397
0.8396	Intermediate Similarity	NPC474927
0.8381	Intermediate Similarity	NPC98633
0.8381	Intermediate Similarity	NPC124053
0.8381	Intermediate Similarity	NPC255655
0.8381	Intermediate Similarity	NPC130302
0.8367	Intermediate Similarity	NPC84018
0.8367	Intermediate Similarity	NPC210214
0.8367	Intermediate Similarity	NPC197158
0.8367	Intermediate Similarity	NPC231060
0.8367	Intermediate Similarity	NPC471624
0.8367	Intermediate Similarity	NPC138245
0.8365	Intermediate Similarity	NPC55973
0.8365	Intermediate Similarity	NPC211224
0.8365	Intermediate Similarity	NPC469729
0.8365	Intermediate Similarity	NPC469733
0.8365	Intermediate Similarity	NPC189663
0.8365	Intermediate Similarity	NPC89860
0.8351	Intermediate Similarity	NPC181594
0.8351	Intermediate Similarity	NPC144739
0.835	Intermediate Similarity	NPC222833
0.835	Intermediate Similarity	NPC295366
0.835	Intermediate Similarity	NPC12823
0.835	Intermediate Similarity	NPC37600
0.835	Intermediate Similarity	NPC4115
0.8333	Intermediate Similarity	NPC469985
0.8318	Intermediate Similarity	NPC52634
0.8318	Intermediate Similarity	NPC471252
0.8318	Intermediate Similarity	NPC132668
0.8317	Intermediate Similarity	NPC121218
0.8317	Intermediate Similarity	NPC253886
0.8302	Intermediate Similarity	NPC470281
0.8302	Intermediate Similarity	NPC471251
0.8298	Intermediate Similarity	NPC471042
0.8286	Intermediate Similarity	NPC252679
0.8286	Intermediate Similarity	NPC118721
0.8286	Intermediate Similarity	NPC471250
0.8286	Intermediate Similarity	NPC469744
0.8283	Intermediate Similarity	NPC256227
0.8283	Intermediate Similarity	NPC219353
0.8283	Intermediate Similarity	NPC193785
0.8283	Intermediate Similarity	NPC104568
0.8269	Intermediate Similarity	NPC471461
0.8269	Intermediate Similarity	NPC67745
0.8269	Intermediate Similarity	NPC471246
0.8265	Intermediate Similarity	NPC153775
0.8265	Intermediate Similarity	NPC29247
0.8265	Intermediate Similarity	NPC289539
0.8265	Intermediate Similarity	NPC292374
0.8265	Intermediate Similarity	NPC261333
0.8265	Intermediate Similarity	NPC111524
0.8265	Intermediate Similarity	NPC215271
0.8265	Intermediate Similarity	NPC91772
0.8265	Intermediate Similarity	NPC101233
0.8265	Intermediate Similarity	NPC129004
0.8265	Intermediate Similarity	NPC104371
0.8247	Intermediate Similarity	NPC476934
0.8247	Intermediate Similarity	NPC278106
0.8247	Intermediate Similarity	NPC299185
0.8241	Intermediate Similarity	NPC243354
0.8235	Intermediate Similarity	NPC170615
0.8235	Intermediate Similarity	NPC164551
0.8224	Intermediate Similarity	NPC476964
0.8218	Intermediate Similarity	NPC94906
0.8208	Intermediate Similarity	NPC471476
0.8208	Intermediate Similarity	NPC473324
0.82	Intermediate Similarity	NPC111187
0.82	Intermediate Similarity	NPC190080
0.8191	Intermediate Similarity	NPC190704
0.8191	Intermediate Similarity	NPC471034
0.8182	Intermediate Similarity	NPC259042
0.8182	Intermediate Similarity	NPC157686

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 NPC267921 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	2128
0.2-0.3	4074
0.3-0.4	1799
0.4-0.5	465
0.5-0.6	213
0.6-0.7	174
0.7-0.8	76
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.783	Intermediate Similarity	NPD6008	Approved
0.77	Intermediate Similarity	NPD8035	Phase 2
0.77	Intermediate Similarity	NPD8034	Phase 2
0.7607	Intermediate Similarity	NPD7492	Approved
0.7593	Intermediate Similarity	NPD5697	Approved
0.7565	Intermediate Similarity	NPD6319	Approved
0.7565	Intermediate Similarity	NPD6054	Approved
0.7542	Intermediate Similarity	NPD6616	Approved
0.7523	Intermediate Similarity	NPD6011	Approved
0.7523	Intermediate Similarity	NPD6899	Approved
0.7523	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6881	Approved
0.7523	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD6016	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.75	Intermediate Similarity	NPD6015	Approved
0.7479	Intermediate Similarity	NPD7078	Approved
0.7477	Intermediate Similarity	NPD6650	Approved
0.7477	Intermediate Similarity	NPD6649	Approved
0.7455	Intermediate Similarity	NPD6373	Approved
0.7455	Intermediate Similarity	NPD6372	Approved
0.7455	Intermediate Similarity	NPD6014	Approved
0.7455	Intermediate Similarity	NPD6012	Approved
0.7455	Intermediate Similarity	NPD6013	Approved
0.7451	Intermediate Similarity	NPD6399	Phase 3
0.7449	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6370	Approved
0.7436	Intermediate Similarity	NPD5988	Approved
0.7431	Intermediate Similarity	NPD5701	Approved
0.7417	Intermediate Similarity	NPD7736	Approved
0.7414	Intermediate Similarity	NPD6059	Approved
0.7387	Intermediate Similarity	NPD7290	Approved
0.7387	Intermediate Similarity	NPD6883	Approved
0.7387	Intermediate Similarity	NPD7102	Approved
0.7353	Intermediate Similarity	NPD6079	Approved
0.7333	Intermediate Similarity	NPD8293	Discontinued
0.7327	Intermediate Similarity	NPD5328	Approved
0.7321	Intermediate Similarity	NPD8130	Phase 1
0.7321	Intermediate Similarity	NPD6617	Approved
0.7321	Intermediate Similarity	NPD6869	Approved
0.7321	Intermediate Similarity	NPD6847	Approved
0.7304	Intermediate Similarity	NPD6009	Approved
0.7264	Intermediate Similarity	NPD7638	Approved
0.7257	Intermediate Similarity	NPD8297	Approved
0.7257	Intermediate Similarity	NPD6882	Approved
0.7238	Intermediate Similarity	NPD4697	Phase 3
0.7238	Intermediate Similarity	NPD5221	Approved
0.7238	Intermediate Similarity	NPD5222	Approved
0.7238	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4634	Approved
0.7203	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5983	Phase 2
0.72	Intermediate Similarity	NPD3618	Phase 1
0.7196	Intermediate Similarity	NPD4696	Approved
0.7196	Intermediate Similarity	NPD5285	Approved
0.7196	Intermediate Similarity	NPD7640	Approved
0.7196	Intermediate Similarity	NPD5286	Approved
0.7196	Intermediate Similarity	NPD7639	Approved
0.717	Intermediate Similarity	NPD4755	Approved
0.717	Intermediate Similarity	NPD7902	Approved
0.717	Intermediate Similarity	NPD5173	Approved
0.7168	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5223	Approved
0.7083	Intermediate Similarity	NPD6118	Approved
0.7083	Intermediate Similarity	NPD6114	Approved
0.7083	Intermediate Similarity	NPD6697	Approved
0.7083	Intermediate Similarity	NPD6115	Approved
0.7083	Intermediate Similarity	NPD8328	Phase 3
0.7083	Intermediate Similarity	NPD7604	Phase 2
0.7073	Intermediate Similarity	NPD7319	Approved
0.7071	Intermediate Similarity	NPD4788	Approved
0.7069	Intermediate Similarity	NPD6274	Approved
0.7064	Intermediate Similarity	NPD5226	Approved
0.7064	Intermediate Similarity	NPD5224	Approved
0.7064	Intermediate Similarity	NPD5211	Phase 2
0.7064	Intermediate Similarity	NPD5225	Approved
0.7064	Intermediate Similarity	NPD4633	Approved
0.7048	Intermediate Similarity	NPD7748	Approved
0.7037	Intermediate Similarity	NPD4700	Approved
0.703	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7515	Phase 2
0.7019	Intermediate Similarity	NPD6411	Approved
0.7009	Intermediate Similarity	NPD7115	Discovery
0.7009	Intermediate Similarity	NPD6084	Phase 2
0.7009	Intermediate Similarity	NPD6317	Approved
0.7009	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD5174	Approved
0.7	Intermediate Similarity	NPD5175	Approved
0.6992	Remote Similarity	NPD6033	Approved
0.6981	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6116	Phase 1
0.6967	Remote Similarity	NPD7507	Approved
0.6967	Remote Similarity	NPD6336	Discontinued
0.6964	Remote Similarity	NPD6412	Phase 2
0.6961	Remote Similarity	NPD3573	Approved
0.6952	Remote Similarity	NPD4202	Approved
0.6949	Remote Similarity	NPD6335	Approved
0.6949	Remote Similarity	NPD6314	Approved
0.6949	Remote Similarity	NPD6313	Approved
0.6947	Remote Similarity	NPD3703	Phase 2
0.6944	Remote Similarity	NPD5696	Approved
0.6944	Remote Similarity	NPD4225	Approved
0.6937	Remote Similarity	NPD5141	Approved
0.6923	Remote Similarity	NPD6868	Approved
0.6903	Remote Similarity	NPD6686	Approved
0.6897	Remote Similarity	NPD8133	Approved
0.6893	Remote Similarity	NPD6903	Approved
0.6893	Remote Similarity	NPD6672	Approved
0.6893	Remote Similarity	NPD5737	Approved
0.6891	Remote Similarity	NPD7101	Approved
0.6891	Remote Similarity	NPD7100	Approved
0.6887	Remote Similarity	NPD5282	Discontinued
0.6887	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6001	Approved
0.6887	Remote Similarity	NPD7900	Approved
0.6875	Remote Similarity	NPD6117	Approved
0.6864	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7146	Approved
0.6863	Remote Similarity	NPD6684	Approved
0.6863	Remote Similarity	NPD7334	Approved
0.6863	Remote Similarity	NPD6409	Approved
0.6863	Remote Similarity	NPD5330	Approved
0.6863	Remote Similarity	NPD7521	Approved
0.6847	Remote Similarity	NPD4754	Approved
0.6842	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD3666	Approved
0.6832	Remote Similarity	NPD3133	Approved
0.6832	Remote Similarity	NPD4786	Approved
0.6832	Remote Similarity	NPD3665	Phase 1
0.6827	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6101	Approved
0.6822	Remote Similarity	NPD5695	Phase 3
0.68	Remote Similarity	NPD3667	Approved
0.6777	Remote Similarity	NPD6921	Approved
0.6771	Remote Similarity	NPD3702	Approved
0.6769	Remote Similarity	NPD6333	Approved
0.6769	Remote Similarity	NPD6334	Approved
0.6757	Remote Similarity	NPD7632	Discontinued
0.6754	Remote Similarity	NPD4729	Approved
0.6754	Remote Similarity	NPD4730	Approved
0.6754	Remote Similarity	NPD5128	Approved
0.6731	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4767	Approved
0.6726	Remote Similarity	NPD4768	Approved
0.6698	Remote Similarity	NPD5281	Approved
0.6698	Remote Similarity	NPD5284	Approved
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5210	Approved
0.6639	Remote Similarity	NPD6908	Approved
0.6639	Remote Similarity	NPD6909	Approved
0.6638	Remote Similarity	NPD5135	Approved
0.6638	Remote Similarity	NPD5250	Approved
0.6638	Remote Similarity	NPD5248	Approved
0.6638	Remote Similarity	NPD5169	Approved
0.6638	Remote Similarity	NPD5249	Phase 3
0.6638	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5247	Approved
0.6638	Remote Similarity	NPD5251	Approved
0.6638	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5779	Approved
0.6636	Remote Similarity	NPD5778	Approved
0.6609	Remote Similarity	NPD5168	Approved
0.6604	Remote Similarity	NPD5207	Approved
0.6602	Remote Similarity	NPD1694	Approved
0.6581	Remote Similarity	NPD5217	Approved
0.6581	Remote Similarity	NPD5127	Approved
0.6581	Remote Similarity	NPD5216	Approved
0.6581	Remote Similarity	NPD5215	Approved
0.6542	Remote Similarity	NPD7637	Suspended
0.6538	Remote Similarity	NPD5279	Phase 3
0.6532	Remote Similarity	NPD6067	Discontinued
0.6509	Remote Similarity	NPD6673	Approved
0.6509	Remote Similarity	NPD6904	Approved
0.6509	Remote Similarity	NPD6080	Approved
0.6484	Remote Similarity	NPD5956	Approved
0.6471	Remote Similarity	NPD4221	Approved
0.6471	Remote Similarity	NPD4223	Phase 3
0.6471	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4224	Phase 2
0.6436	Remote Similarity	NPD7525	Registered
0.6421	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5167	Approved
0.6415	Remote Similarity	NPD5208	Approved
0.6393	Remote Similarity	NPD7328	Approved
0.6393	Remote Similarity	NPD7327	Approved
0.6389	Remote Similarity	NPD5693	Phase 1

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