NPASS Compound

Structure

NPC471094 OpenBabel07101719252D 29 33 0 0 1 0 0 0 0 0999 V2000 2.8998 -2.3308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2139 2.6016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7600 0.8398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4225 -2.6741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0751 -2.1536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8545 -1.1080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 -0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3307 -2.0217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7601 0.8548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6182 -0.3693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 -2.0217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7860 2.5866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1397 -2.6095 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0215 -1.4400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2256 -1.4587 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6182 -0.3693 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6397 -1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2471 -0.0187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6074 -1.0893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6397 -1.0707 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6289 -0.3507 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2989 3.4451 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2106 -2.4586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2275 -0.2617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0150 0.9999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6288 -0.3357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2730 1.7132 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 11 2 0 0 0 0 2 12 1 0 0 0 0 4 5 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 19 1 0 0 0 0 8 13 1 0 0 0 0 8 21 1 0 0 0 0 9 19 1 0 0 0 0 9 28 1 0 0 0 0 10 29 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 23 2 0 0 0 0 12 28 1 0 0 0 0 13 4 1 6 0 0 0 14 20 1 1 0 0 0 14 21 1 0 0 0 0 15 20 1 1 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 17 25 2 0 0 0 0 18 22 1 6 0 0 0 18 26 1 0 0 0 0 19 3 1 6 0 0 0 20 10 1 1 0 0 0 21 22 1 1 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.2
Volume:	399.908
LogP:	0.831
LogD:	0.95
LogS:	-3.651
# Rotatable Bonds:	3
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.462
Synthetic Accessibility Score:	6.842
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.316
MDCK Permeability:	1.2313124898355454e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.454
Human Intestinal Absorption (HIA):	0.268
20% Bioavailability (F20%):	0.827
30% Bioavailability (F30%):	0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.645
Plasma Protein Binding (PPB):	62.04512023925781%
Volume Distribution (VD):	1.114
Pgp-substrate:	53.73260498046875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.486
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.597
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.206
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	1.992
Half-life (T1/2):	0.782

ADMET: Toxicity

hERG Blockers:	0.191
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.117
AMES Toxicity:	0.242
Rat Oral Acute Toxicity:	0.781
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.312
Carcinogencity:	0.647
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC471094

Natural Product ID:	NPC471094
*Common Name:**	UDOQTYDWKGQXFY-LQSNDDGTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UDOQTYDWKGQXFY-LQSNDDGTSA-N
Standard InCHI:	InChI=1S/C22H30O7/c1-11-13-4-5-14-20-10-29-22(27,21(14,8-13)17(11)25)18(26)16(20)19(3,7-6-15(20)24)9-28-12(2)23/h13-16,18,24,26-27H,1,4-10H2,2-3H3/t13-,14+,15+,16-,18+,19+,20-,21+,22+/m1/s1
SMILES:	CC(=O)OCC1(CCC(C23C1C(C(C45C2CCC(C4)C(=C)C5=O)(OC3)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2368598
PubChem CID:	73355983
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO26266	Isodon japonicus	Species	Lamiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	5900.0	nM	PMID[557376]

☑ 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 NPC471094 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	288
0.1-0.2	1978
0.2-0.3	6007
0.3-0.4	10453
0.4-0.5	10357
0.5-0.6	6065
0.6-0.7	4403
0.7-0.8	2349
0.8-0.85	636
0.85-0.9	87
0.9-0.95	28
0.95-1	46

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473410
1.0	High Similarity	NPC469984
0.9899	High Similarity	NPC471474
0.9802	High Similarity	NPC474786
0.9802	High Similarity	NPC320383
0.9802	High Similarity	NPC85391
0.9802	High Similarity	NPC137104
0.98	High Similarity	NPC63841
0.9798	High Similarity	NPC56656
0.9798	High Similarity	NPC307660
0.9798	High Similarity	NPC130511
0.9706	High Similarity	NPC213320
0.9703	High Similarity	NPC131903
0.9703	High Similarity	NPC274827
0.9703	High Similarity	NPC102741
0.97	High Similarity	NPC186054
0.9612	High Similarity	NPC473352
0.9612	High Similarity	NPC474927
0.9612	High Similarity	NPC473397
0.9608	High Similarity	NPC471093
0.9604	High Similarity	NPC189663
0.9604	High Similarity	NPC89860
0.9519	High Similarity	NPC132668
0.9515	High Similarity	NPC29505
0.951	High Similarity	NPC252679
0.951	High Similarity	NPC118721
0.9417	High Similarity	NPC471476
0.9412	High Similarity	NPC55973
0.94	High Similarity	NPC139347
0.9394	High Similarity	NPC14634
0.934	High Similarity	NPC88945
0.934	High Similarity	NPC229752
0.9333	High Similarity	NPC471252
0.9333	High Similarity	NPC194273
0.9327	High Similarity	NPC63244
0.9314	High Similarity	NPC471461
0.9314	High Similarity	NPC67745
0.9307	High Similarity	NPC202793
0.9252	High Similarity	NPC78836
0.9245	High Similarity	NPC243354
0.9238	High Similarity	NPC471244
0.9231	High Similarity	NPC473324
0.9223	High Similarity	NPC232133
0.9208	High Similarity	NPC209298
0.9208	High Similarity	NPC277074
0.9151	High Similarity	NPC320118
0.9151	High Similarity	NPC471248
0.9151	High Similarity	NPC94141
0.9143	High Similarity	NPC56025
0.9143	High Similarity	NPC122339
0.9143	High Similarity	NPC471243
0.9135	High Similarity	NPC469983
0.9126	High Similarity	NPC166993
0.91	High Similarity	NPC470388
0.9074	High Similarity	NPC473304
0.9065	High Similarity	NPC17165
0.9057	High Similarity	NPC157929
0.9057	High Similarity	NPC473303
0.9057	High Similarity	NPC471245
0.9057	High Similarity	NPC145625
0.9038	High Similarity	NPC273155
0.9029	High Similarity	NPC200957
0.9029	High Similarity	NPC138908
0.902	High Similarity	NPC122811
0.9	High Similarity	NPC474793
0.8942	High Similarity	NPC96333
0.8942	High Similarity	NPC469746
0.8942	High Similarity	NPC88833
0.8932	High Similarity	NPC301787
0.8932	High Similarity	NPC474558
0.8922	High Similarity	NPC475803
0.8922	High Similarity	NPC309388
0.8857	High Similarity	NPC218123
0.8857	High Similarity	NPC112895
0.8857	High Similarity	NPC231278
0.8846	High Similarity	NPC222833
0.8835	High Similarity	NPC96217
0.8824	High Similarity	NPC46848
0.8824	High Similarity	NPC236585
0.8824	High Similarity	NPC148279
0.8824	High Similarity	NPC252614
0.8812	High Similarity	NPC471038
0.8785	High Similarity	NPC329953
0.8774	High Similarity	NPC469744
0.8762	High Similarity	NPC61071
0.875	High Similarity	NPC101842
0.8738	High Similarity	NPC275990
0.8727	High Similarity	NPC218970
0.8725	High Similarity	NPC267921
0.8704	High Similarity	NPC205534
0.87	High Similarity	NPC470232
0.8692	High Similarity	NPC98069
0.8692	High Similarity	NPC49730
0.8679	High Similarity	NPC469729
0.8679	High Similarity	NPC469733
0.8667	High Similarity	NPC4115
0.8667	High Similarity	NPC103172
0.8667	High Similarity	NPC12823
0.8667	High Similarity	NPC164600
0.8654	High Similarity	NPC87927
0.8641	High Similarity	NPC52899
0.8641	High Similarity	NPC471790
0.8641	High Similarity	NPC163963
0.8641	High Similarity	NPC289148
0.8627	High Similarity	NPC38471
0.8627	High Similarity	NPC98837
0.8627	High Similarity	NPC162459
0.8627	High Similarity	NPC20479
0.8627	High Similarity	NPC89099
0.8627	High Similarity	NPC28864
0.8627	High Similarity	NPC26270
0.8627	High Similarity	NPC38296
0.8624	High Similarity	NPC73986
0.8614	High Similarity	NPC329910
0.8614	High Similarity	NPC200054
0.8614	High Similarity	NPC29410
0.86	High Similarity	NPC475118
0.86	High Similarity	NPC470386
0.86	High Similarity	NPC470385
0.8571	High Similarity	NPC13149
0.8559	High Similarity	NPC470171
0.8558	High Similarity	NPC76866
0.8558	High Similarity	NPC88203
0.8558	High Similarity	NPC214946
0.8558	High Similarity	NPC470172
0.8558	High Similarity	NPC148628
0.8558	High Similarity	NPC246736
0.8558	High Similarity	NPC304832
0.8558	High Similarity	NPC471254
0.8558	High Similarity	NPC286519
0.8544	High Similarity	NPC287676
0.8544	High Similarity	NPC293866
0.8532	High Similarity	NPC207845
0.8532	High Similarity	NPC472719
0.8529	High Similarity	NPC10864
0.8515	High Similarity	NPC98639
0.8515	High Similarity	NPC470229
0.8476	Intermediate Similarity	NPC473406
0.8476	Intermediate Similarity	NPC471253
0.8476	Intermediate Similarity	NPC216114
0.8447	Intermediate Similarity	NPC16911
0.8447	Intermediate Similarity	NPC78427
0.844	Intermediate Similarity	NPC274833
0.844	Intermediate Similarity	NPC201992
0.844	Intermediate Similarity	NPC11035
0.8431	Intermediate Similarity	NPC104568
0.8431	Intermediate Similarity	NPC470387
0.8431	Intermediate Similarity	NPC13949
0.8431	Intermediate Similarity	NPC256227
0.8426	Intermediate Similarity	NPC8431
0.8416	Intermediate Similarity	NPC47853
0.8411	Intermediate Similarity	NPC471246
0.8411	Intermediate Similarity	NPC201908
0.8411	Intermediate Similarity	NPC176949
0.84	Intermediate Similarity	NPC250753
0.84	Intermediate Similarity	NPC198242
0.84	Intermediate Similarity	NPC211403
0.8396	Intermediate Similarity	NPC98603
0.8396	Intermediate Similarity	NPC84928
0.8365	Intermediate Similarity	NPC291785
0.8365	Intermediate Similarity	NPC127408
0.8364	Intermediate Similarity	NPC470543
0.8364	Intermediate Similarity	NPC11252
0.8364	Intermediate Similarity	NPC476964
0.8364	Intermediate Similarity	NPC289312
0.835	Intermediate Similarity	NPC96839
0.8349	Intermediate Similarity	NPC100908
0.8333	Intermediate Similarity	NPC476961
0.8333	Intermediate Similarity	NPC41070
0.8319	Intermediate Similarity	NPC297179
0.8319	Intermediate Similarity	NPC204552
0.8319	Intermediate Similarity	NPC188667
0.8318	Intermediate Similarity	NPC285927
0.8317	Intermediate Similarity	NPC294263
0.8304	Intermediate Similarity	NPC472718
0.8302	Intermediate Similarity	NPC159442
0.8288	Intermediate Similarity	NPC51978
0.8288	Intermediate Similarity	NPC146563
0.8286	Intermediate Similarity	NPC39683
0.8273	Intermediate Similarity	NPC272242
0.8273	Intermediate Similarity	NPC94650
0.8269	Intermediate Similarity	NPC469725
0.8261	Intermediate Similarity	NPC477046
0.8261	Intermediate Similarity	NPC102822
0.8261	Intermediate Similarity	NPC470478
0.8257	Intermediate Similarity	NPC143706
0.8257	Intermediate Similarity	NPC240125
0.8257	Intermediate Similarity	NPC51947
0.8257	Intermediate Similarity	NPC472534
0.8257	Intermediate Similarity	NPC91583
0.8257	Intermediate Similarity	NPC473844
0.8246	Intermediate Similarity	NPC469488
0.823	Intermediate Similarity	NPC474654
0.823	Intermediate Similarity	NPC122033
0.823	Intermediate Similarity	NPC470854
0.823	Intermediate Similarity	NPC287343
0.823	Intermediate Similarity	NPC97908
0.8224	Intermediate Similarity	NPC96268
0.8224	Intermediate Similarity	NPC244247
0.8218	Intermediate Similarity	NPC470230

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 NPC471094 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	2343
0.2-0.3	3950
0.3-0.4	1656
0.4-0.5	478
0.5-0.6	244
0.6-0.7	145
0.7-0.8	48
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD8328	Phase 3
0.7863	Intermediate Similarity	NPD6319	Approved
0.7807	Intermediate Similarity	NPD8133	Approved
0.7768	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7492	Approved
0.7712	Intermediate Similarity	NPD6054	Approved
0.7705	Intermediate Similarity	NPD7736	Approved
0.7686	Intermediate Similarity	NPD6616	Approved
0.7652	Intermediate Similarity	NPD4632	Approved
0.7647	Intermediate Similarity	NPD6015	Approved
0.7647	Intermediate Similarity	NPD6016	Approved
0.7642	Intermediate Similarity	NPD7319	Approved
0.7623	Intermediate Similarity	NPD7078	Approved
0.7607	Intermediate Similarity	NPD6009	Approved
0.7589	Intermediate Similarity	NPD6412	Phase 2
0.7583	Intermediate Similarity	NPD5988	Approved
0.7583	Intermediate Similarity	NPD6370	Approved
0.7563	Intermediate Similarity	NPD6059	Approved
0.7541	Intermediate Similarity	NPD7507	Approved
0.7524	Intermediate Similarity	NPD8034	Phase 2
0.7524	Intermediate Similarity	NPD8035	Phase 2
0.748	Intermediate Similarity	NPD8293	Discontinued
0.7458	Intermediate Similarity	NPD7115	Discovery
0.7434	Intermediate Similarity	NPD5697	Approved
0.7414	Intermediate Similarity	NPD6882	Approved
0.7414	Intermediate Similarity	NPD8297	Approved
0.7391	Intermediate Similarity	NPD4634	Approved
0.7368	Intermediate Similarity	NPD6686	Approved
0.7368	Intermediate Similarity	NPD6899	Approved
0.7368	Intermediate Similarity	NPD6881	Approved
0.7345	Intermediate Similarity	NPD6675	Approved
0.7345	Intermediate Similarity	NPD6402	Approved
0.7345	Intermediate Similarity	NPD7128	Approved
0.7345	Intermediate Similarity	NPD5739	Approved
0.7328	Intermediate Similarity	NPD6650	Approved
0.7328	Intermediate Similarity	NPD6649	Approved
0.7304	Intermediate Similarity	NPD6012	Approved
0.7304	Intermediate Similarity	NPD6014	Approved
0.7304	Intermediate Similarity	NPD6373	Approved
0.7304	Intermediate Similarity	NPD6372	Approved
0.7304	Intermediate Similarity	NPD6013	Approved
0.7282	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5701	Approved
0.7257	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7290	Approved
0.7241	Intermediate Similarity	NPD7102	Approved
0.7241	Intermediate Similarity	NPD6883	Approved
0.7217	Intermediate Similarity	NPD6011	Approved
0.7217	Intermediate Similarity	NPD7320	Approved
0.7213	Intermediate Similarity	NPD6921	Approved
0.7213	Intermediate Similarity	NPD5983	Phase 2
0.7193	Intermediate Similarity	NPD6008	Approved
0.7179	Intermediate Similarity	NPD6869	Approved
0.7179	Intermediate Similarity	NPD6847	Approved
0.7179	Intermediate Similarity	NPD8130	Phase 1
0.7179	Intermediate Similarity	NPD6617	Approved
0.7155	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6399	Phase 3
0.7117	Intermediate Similarity	NPD4225	Approved
0.7097	Intermediate Similarity	NPD7604	Phase 2
0.7054	Intermediate Similarity	NPD5286	Approved
0.7054	Intermediate Similarity	NPD5285	Approved
0.7054	Intermediate Similarity	NPD4696	Approved
0.7049	Intermediate Similarity	NPD7516	Approved
0.7037	Intermediate Similarity	NPD6079	Approved
0.7027	Intermediate Similarity	NPD7902	Approved
0.7027	Intermediate Similarity	NPD4755	Approved
0.7009	Intermediate Similarity	NPD5328	Approved
0.7008	Intermediate Similarity	NPD6033	Approved
0.6992	Remote Similarity	NPD8294	Approved
0.6992	Remote Similarity	NPD8377	Approved
0.6984	Remote Similarity	NPD6336	Discontinued
0.6967	Remote Similarity	NPD7327	Approved
0.6967	Remote Similarity	NPD7328	Approved
0.6964	Remote Similarity	NPD7638	Approved
0.6949	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6274	Approved
0.6937	Remote Similarity	NPD5222	Approved
0.6937	Remote Similarity	NPD4697	Phase 3
0.6937	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5221	Approved
0.6935	Remote Similarity	NPD8296	Approved
0.6935	Remote Similarity	NPD8378	Approved
0.6935	Remote Similarity	NPD8517	Approved
0.6935	Remote Similarity	NPD8335	Approved
0.6935	Remote Similarity	NPD8515	Approved
0.6935	Remote Similarity	NPD8380	Approved
0.6935	Remote Similarity	NPD8516	Approved
0.6935	Remote Similarity	NPD8033	Approved
0.6935	Remote Similarity	NPD8379	Approved
0.6935	Remote Similarity	NPD8513	Phase 3
0.693	Remote Similarity	NPD5226	Approved
0.693	Remote Similarity	NPD5225	Approved
0.693	Remote Similarity	NPD4633	Approved
0.693	Remote Similarity	NPD5224	Approved
0.693	Remote Similarity	NPD5211	Phase 2
0.6909	Remote Similarity	NPD7748	Approved
0.6903	Remote Similarity	NPD4700	Approved
0.6903	Remote Similarity	NPD7640	Approved
0.6903	Remote Similarity	NPD7639	Approved
0.6891	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3618	Phase 1
0.6881	Remote Similarity	NPD7515	Phase 2
0.6875	Remote Similarity	NPD5173	Approved
0.687	Remote Similarity	NPD5174	Approved
0.687	Remote Similarity	NPD5175	Approved
0.6842	Remote Similarity	NPD5223	Approved
0.6822	Remote Similarity	NPD3573	Approved
0.681	Remote Similarity	NPD5141	Approved
0.68	Remote Similarity	NPD7503	Approved
0.6774	Remote Similarity	NPD7101	Approved
0.6774	Remote Similarity	NPD7100	Approved
0.6765	Remote Similarity	NPD6697	Approved
0.6765	Remote Similarity	NPD6118	Approved
0.6765	Remote Similarity	NPD6114	Approved
0.6765	Remote Similarity	NPD6115	Approved
0.6757	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7900	Approved
0.6748	Remote Similarity	NPD6317	Approved
0.6727	Remote Similarity	NPD6411	Approved
0.6726	Remote Similarity	NPD6084	Phase 2
0.6726	Remote Similarity	NPD6083	Phase 2
0.6696	Remote Similarity	NPD1700	Approved
0.6695	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6335	Approved
0.6694	Remote Similarity	NPD6313	Approved
0.6694	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD5696	Approved
0.6639	Remote Similarity	NPD5128	Approved
0.6639	Remote Similarity	NPD4729	Approved
0.6639	Remote Similarity	NPD4730	Approved
0.6634	Remote Similarity	NPD3703	Phase 2
0.661	Remote Similarity	NPD4767	Approved
0.661	Remote Similarity	NPD4768	Approved
0.6604	Remote Similarity	NPD4788	Approved
0.6581	Remote Similarity	NPD4754	Approved
0.6574	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6117	Approved
0.6562	Remote Similarity	NPD6067	Discontinued
0.6549	Remote Similarity	NPD5695	Phase 3
0.6545	Remote Similarity	NPD6101	Approved
0.6545	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4786	Approved
0.6538	Remote Similarity	NPD8074	Phase 3
0.6535	Remote Similarity	NPD6909	Approved
0.6535	Remote Similarity	NPD6908	Approved
0.6529	Remote Similarity	NPD5247	Approved
0.6529	Remote Similarity	NPD5249	Phase 3
0.6529	Remote Similarity	NPD6371	Approved
0.6529	Remote Similarity	NPD5248	Approved
0.6529	Remote Similarity	NPD5250	Approved
0.6529	Remote Similarity	NPD5251	Approved
0.6515	Remote Similarity	NPD5956	Approved
0.6509	Remote Similarity	NPD3667	Approved
0.6496	Remote Similarity	NPD7632	Discontinued
0.6475	Remote Similarity	NPD5217	Approved
0.6475	Remote Similarity	NPD5215	Approved
0.6475	Remote Similarity	NPD5216	Approved
0.6455	Remote Similarity	NPD5737	Approved
0.6455	Remote Similarity	NPD6672	Approved
0.6455	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6334	Approved
0.6423	Remote Similarity	NPD6333	Approved
0.6422	Remote Similarity	NPD6684	Approved
0.6422	Remote Similarity	NPD6409	Approved
0.6422	Remote Similarity	NPD7521	Approved
0.6422	Remote Similarity	NPD5330	Approved
0.6422	Remote Similarity	NPD7334	Approved
0.6422	Remote Similarity	NPD7146	Approved
0.6415	Remote Similarity	NPD1779	Approved
0.6415	Remote Similarity	NPD1780	Approved
0.6404	Remote Similarity	NPD5210	Approved
0.6404	Remote Similarity	NPD4629	Approved
0.6404	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6940	Discontinued
0.6396	Remote Similarity	NPD4753	Phase 2
0.6393	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5169	Approved
0.6393	Remote Similarity	NPD5135	Approved
0.6389	Remote Similarity	NPD3665	Phase 1
0.6389	Remote Similarity	NPD3666	Approved
0.6389	Remote Similarity	NPD3133	Approved
0.6373	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD8171	Discontinued
0.6372	Remote Similarity	NPD5779	Approved
0.6372	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD5168	Approved
0.6341	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5127	Approved
0.6316	Remote Similarity	NPD5282	Discontinued
0.6311	Remote Similarity	NPD3702	Approved
0.6306	Remote Similarity	NPD6903	Approved
0.6296	Remote Similarity	NPD3669	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