NPASS Compound

Structure

NPC4115 OpenBabel07101718232D 28 32 0 0 1 0 0 0 0 0999 V2000 3.1484 0.5824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3812 -2.4897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3455 -2.4753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9334 -1.3232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0097 -0.0458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2195 0.3495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4367 -0.5968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8301 -0.2586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2794 0.4116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3518 -1.6654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2312 0.2844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7593 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2443 -1.3092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3726 -0.2766 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4470 -1.2912 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9584 -1.3272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4510 0.8513 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9332 -0.6328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6708 0.2844 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8509 -1.6474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1959 -0.7017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2339 -0.6148 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9688 -0.6328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4204 1.8164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2894 -1.7609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5001 -1.4130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2307 -1.2924 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 20 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 24 1 6 0 0 0 13 20 1 0 0 0 0 13 22 1 6 0 0 0 14 22 1 6 0 0 0 14 23 1 0 0 0 0 15 20 1 0 0 0 0 15 25 1 6 0 0 0 16 23 1 1 0 0 0 16 27 1 0 0 0 0 17 11 1 1 0 0 0 17 19 1 0 0 0 0 18 26 2 0 0 0 0 19 23 1 6 0 0 0 19 28 1 0 0 0 0 21 27 1 0 0 0 0 21 28 1 0 0 0 0 22 6 1 6 0 0 0 23 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.24
Volume:	402.26
LogP:	2.15
LogD:	2.432
LogS:	-3.547
# Rotatable Bonds:	0
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	6.209
Fsp3:	0.87
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:	-4.779
MDCK Permeability:	5.864119157195091e-05
Pgp-inhibitor:	0.375
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.613
Plasma Protein Binding (PPB):	30.070709228515625%
Volume Distribution (VD):	1.35
Pgp-substrate:	57.76625442504883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.133
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.69
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	8.745
Half-life (T1/2):	0.596

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.182
Drug-inuced Liver Injury (DILI):	0.107
AMES Toxicity:	0.173
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.987
Skin Sensitization:	0.672
Carcinogencity:	0.182
Eye Corrosion:	0.012
Eye Irritation:	0.092
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC4115

Natural Product ID:	NPC4115
*Common Name:**	GOYFWJSFOLAGQI-KSTWMERRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GOYFWJSFOLAGQI-KSTWMERRSA-N
Standard InCHI:	InChI=1S/C23H34O5/c1-11-17-12(24)9-14-22(6)8-7-15(25)20(2,3)13(22)10-16-23(14,18(11)26)19(17)28-21(4,5)27-16/h12-17,19,24-25H,1,7-10H2,2-6H3/t12-,13+,14-,15+,16+,17+,19+,22+,23-/m0/s1
SMILES:	C=C1[C@@H]2[C@H](C[C@H]3[C@]4(C)CC[C@H](C(C)(C)[C@H]4C[C@@H]4[C@@]3(C1=O)[C@@H]2OC(C)(C)O4)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL564129
PubChem CID:	44179177
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
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425589]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[29286250]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24459	Isodon pharicus	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	=	3560.0	nM	PMID[537156]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6020.0	nM	PMID[537156]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	IC50	>	10000.0	nM	PMID[537156]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[537156]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[537156]

☑ 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 NPC4115 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	254
0.1-0.2	1873
0.2-0.3	5942
0.3-0.4	10020
0.4-0.5	11183
0.5-0.6	5974
0.6-0.7	4658
0.7-0.8	2491
0.8-0.85	137
0.85-0.9	133
0.9-0.95	30
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9691	High Similarity	NPC475803
0.9691	High Similarity	NPC309388
0.9596	High Similarity	NPC12823
0.9406	High Similarity	NPC469733
0.9406	High Similarity	NPC469729
0.9388	High Similarity	NPC471790
0.932	High Similarity	NPC329953
0.9314	High Similarity	NPC469744
0.93	High Similarity	NPC202793
0.9293	High Similarity	NPC88203
0.9293	High Similarity	NPC246736
0.9293	High Similarity	NPC214946
0.9293	High Similarity	NPC148628
0.9293	High Similarity	NPC304832
0.9293	High Similarity	NPC286519
0.9293	High Similarity	NPC76866
0.9231	High Similarity	NPC471245
0.9216	High Similarity	NPC55973
0.92	High Similarity	NPC139347
0.9192	High Similarity	NPC289148
0.9192	High Similarity	NPC52899
0.9192	High Similarity	NPC163963
0.9192	High Similarity	NPC14634
0.9143	High Similarity	NPC471248
0.9135	High Similarity	NPC122339
0.9118	High Similarity	NPC67745
0.9118	High Similarity	NPC469746
0.9118	High Similarity	NPC471461
0.9109	High Similarity	NPC13149
0.9091	High Similarity	NPC287676
0.9048	High Similarity	NPC471244
0.9048	High Similarity	NPC473303
0.9038	High Similarity	NPC473324
0.9038	High Similarity	NPC471093
0.9029	High Similarity	NPC189663
0.9029	High Similarity	NPC89860
0.901	High Similarity	NPC87927
0.9	High Similarity	NPC46848
0.899	High Similarity	NPC16911
0.899	High Similarity	NPC78427
0.8969	High Similarity	NPC215271
0.8969	High Similarity	NPC29247
0.8969	High Similarity	NPC261333
0.8969	High Similarity	NPC91772
0.8969	High Similarity	NPC292374
0.8969	High Similarity	NPC101233
0.8969	High Similarity	NPC111524
0.8969	High Similarity	NPC153775
0.8969	High Similarity	NPC104371
0.8969	High Similarity	NPC129004
0.8969	High Similarity	NPC289539
0.8962	High Similarity	NPC471252
0.8952	High Similarity	NPC63244
0.8952	High Similarity	NPC29505
0.8942	High Similarity	NPC118721
0.8942	High Similarity	NPC252679
0.8922	High Similarity	NPC98603
0.8922	High Similarity	NPC84928
0.8922	High Similarity	NPC474558
0.8911	High Similarity	NPC275990
0.8889	High Similarity	NPC473304
0.8868	High Similarity	NPC474927
0.8868	High Similarity	NPC145625
0.8866	High Similarity	NPC144739
0.8866	High Similarity	NPC181594
0.8857	High Similarity	NPC471476
0.8846	High Similarity	NPC112895
0.8846	High Similarity	NPC63841
0.8846	High Similarity	NPC231278
0.8846	High Similarity	NPC218123
0.8835	High Similarity	NPC307660
0.8835	High Similarity	NPC130511
0.8824	High Similarity	NPC216114
0.88	High Similarity	NPC28864
0.88	High Similarity	NPC20479
0.88	High Similarity	NPC38296
0.88	High Similarity	NPC98837
0.88	High Similarity	NPC471038
0.88	High Similarity	NPC162459
0.88	High Similarity	NPC474793
0.88	High Similarity	NPC38471
0.8796	High Similarity	NPC88945
0.8788	High Similarity	NPC135548
0.8788	High Similarity	NPC13949
0.8788	High Similarity	NPC329910
0.8788	High Similarity	NPC264979
0.8785	High Similarity	NPC94141
0.8774	High Similarity	NPC213320
0.8763	High Similarity	NPC476168
0.8763	High Similarity	NPC299185
0.8762	High Similarity	NPC469983
0.8762	High Similarity	NPC102741
0.875	High Similarity	NPC186054
0.8713	High Similarity	NPC293866
0.8704	High Similarity	NPC17165
0.8692	High Similarity	NPC157929
0.8692	High Similarity	NPC473397
0.8692	High Similarity	NPC473352
0.8687	High Similarity	NPC470232
0.8687	High Similarity	NPC470229
0.8687	High Similarity	NPC210214
0.8687	High Similarity	NPC138245
0.8687	High Similarity	NPC231060
0.8687	High Similarity	NPC84018
0.8679	High Similarity	NPC137104
0.8679	High Similarity	NPC474786
0.8679	High Similarity	NPC320383
0.8679	High Similarity	NPC85391
0.8667	High Similarity	NPC471094
0.8667	High Similarity	NPC473410
0.8667	High Similarity	NPC232133
0.8667	High Similarity	NPC469984
0.8667	High Similarity	NPC273155
0.866	High Similarity	NPC80401
0.866	High Similarity	NPC180849
0.866	High Similarity	NPC261994
0.866	High Similarity	NPC470378
0.866	High Similarity	NPC149761
0.8654	High Similarity	NPC200957
0.8654	High Similarity	NPC138908
0.8654	High Similarity	NPC37600
0.8627	High Similarity	NPC236585
0.8624	High Similarity	NPC229752
0.8614	High Similarity	NPC89099
0.8611	High Similarity	NPC132668
0.86	High Similarity	NPC200054
0.86	High Similarity	NPC140242
0.86	High Similarity	NPC29410
0.8598	High Similarity	NPC471243
0.8586	High Similarity	NPC470386
0.8586	High Similarity	NPC475118
0.8586	High Similarity	NPC47853
0.8586	High Similarity	NPC191094
0.8586	High Similarity	NPC470385
0.8586	High Similarity	NPC302008
0.8585	High Similarity	NPC131903
0.8585	High Similarity	NPC274827
0.8571	High Similarity	NPC166993
0.8571	High Similarity	NPC96333
0.8571	High Similarity	NPC61071
0.8571	High Similarity	NPC201908
0.8571	High Similarity	NPC176949
0.8571	High Similarity	NPC471474
0.8571	High Similarity	NPC88833
0.8545	High Similarity	NPC78836
0.8532	High Similarity	NPC243354
0.8529	High Similarity	NPC156324
0.8529	High Similarity	NPC127408
0.8529	High Similarity	NPC55503
0.8529	High Similarity	NPC291785
0.8515	High Similarity	NPC10864
0.8505	High Similarity	NPC98069
0.8505	High Similarity	NPC49730
0.85	High Similarity	NPC98639
0.8485	Intermediate Similarity	NPC294263
0.8485	Intermediate Similarity	NPC59350
0.8485	Intermediate Similarity	NPC59170
0.8476	Intermediate Similarity	NPC56656
0.8476	Intermediate Similarity	NPC164600
0.8476	Intermediate Similarity	NPC295366
0.8476	Intermediate Similarity	NPC103172
0.8462	Intermediate Similarity	NPC209298
0.8462	Intermediate Similarity	NPC96217
0.8462	Intermediate Similarity	NPC277074
0.8462	Intermediate Similarity	NPC470310
0.8462	Intermediate Similarity	NPC122811
0.8447	Intermediate Similarity	NPC121218
0.8447	Intermediate Similarity	NPC253886
0.8447	Intermediate Similarity	NPC148279
0.8426	Intermediate Similarity	NPC270586
0.8416	Intermediate Similarity	NPC470387
0.8411	Intermediate Similarity	NPC8431
0.84	Intermediate Similarity	NPC64006
0.8384	Intermediate Similarity	NPC470230
0.8384	Intermediate Similarity	NPC211403
0.8384	Intermediate Similarity	NPC250753
0.8384	Intermediate Similarity	NPC198242
0.8381	Intermediate Similarity	NPC96268
0.8381	Intermediate Similarity	NPC301787
0.8381	Intermediate Similarity	NPC101842
0.8365	Intermediate Similarity	NPC170615
0.8351	Intermediate Similarity	NPC174619
0.8351	Intermediate Similarity	NPC259009
0.8351	Intermediate Similarity	NPC153604
0.8351	Intermediate Similarity	NPC165895
0.835	Intermediate Similarity	NPC470388
0.835	Intermediate Similarity	NPC94906
0.835	Intermediate Similarity	NPC267921
0.8349	Intermediate Similarity	NPC476964
0.8333	Intermediate Similarity	NPC111187
0.8333	Intermediate Similarity	NPC190080
0.8318	Intermediate Similarity	NPC211224
0.8317	Intermediate Similarity	NPC29112
0.8302	Intermediate Similarity	NPC222833
0.8286	Intermediate Similarity	NPC159442
0.8286	Intermediate Similarity	NPC266
0.8273	Intermediate Similarity	NPC194273
0.8273	Intermediate Similarity	NPC73986
0.8269	Intermediate Similarity	NPC71706
0.8269	Intermediate Similarity	NPC295276

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 NPC4115 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	2255
0.2-0.3	4053
0.3-0.4	1661
0.4-0.5	479
0.5-0.6	225
0.6-0.7	165
0.7-0.8	60
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
0.7845	Intermediate Similarity	NPD6054	Approved
0.7712	Intermediate Similarity	NPD6370	Approved
0.7692	Intermediate Similarity	NPD6059	Approved
0.7686	Intermediate Similarity	NPD7736	Approved
0.7627	Intermediate Similarity	NPD6015	Approved
0.7627	Intermediate Similarity	NPD6016	Approved
0.7623	Intermediate Similarity	NPD7319	Approved
0.7583	Intermediate Similarity	NPD7492	Approved
0.7568	Intermediate Similarity	NPD6412	Phase 2
0.7563	Intermediate Similarity	NPD5988	Approved
0.7544	Intermediate Similarity	NPD6882	Approved
0.7521	Intermediate Similarity	NPD6616	Approved
0.75	Intermediate Similarity	NPD8328	Phase 3
0.75	Intermediate Similarity	NPD8034	Phase 2
0.75	Intermediate Similarity	NPD8035	Phase 2
0.7459	Intermediate Similarity	NPD7078	Approved
0.7436	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7507	Approved
0.7345	Intermediate Similarity	NPD6899	Approved
0.7345	Intermediate Similarity	NPD6881	Approved
0.7345	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6079	Approved
0.7328	Intermediate Similarity	NPD8133	Approved
0.7321	Intermediate Similarity	NPD6402	Approved
0.7321	Intermediate Similarity	NPD5739	Approved
0.7321	Intermediate Similarity	NPD6675	Approved
0.7321	Intermediate Similarity	NPD7128	Approved
0.7317	Intermediate Similarity	NPD8293	Discontinued
0.7308	Intermediate Similarity	NPD5328	Approved
0.7304	Intermediate Similarity	NPD6649	Approved
0.7304	Intermediate Similarity	NPD6650	Approved
0.7288	Intermediate Similarity	NPD6009	Approved
0.7281	Intermediate Similarity	NPD6372	Approved
0.7281	Intermediate Similarity	NPD6373	Approved
0.7257	Intermediate Similarity	NPD5697	Approved
0.725	Intermediate Similarity	NPD6319	Approved
0.7232	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4788	Approved
0.7217	Intermediate Similarity	NPD7290	Approved
0.7217	Intermediate Similarity	NPD7102	Approved
0.7217	Intermediate Similarity	NPD6883	Approved
0.7217	Intermediate Similarity	NPD4634	Approved
0.7193	Intermediate Similarity	NPD7320	Approved
0.7182	Intermediate Similarity	NPD5286	Approved
0.7182	Intermediate Similarity	NPD5285	Approved
0.7182	Intermediate Similarity	NPD4696	Approved
0.7168	Intermediate Similarity	NPD6008	Approved
0.7156	Intermediate Similarity	NPD4755	Approved
0.7155	Intermediate Similarity	NPD8130	Phase 1
0.7155	Intermediate Similarity	NPD6617	Approved
0.7155	Intermediate Similarity	NPD6869	Approved
0.7155	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD7115	Discovery
0.713	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6013	Approved
0.713	Intermediate Similarity	NPD6012	Approved
0.713	Intermediate Similarity	NPD6014	Approved
0.712	Intermediate Similarity	NPD6033	Approved
0.7105	Intermediate Similarity	NPD5701	Approved
0.7103	Intermediate Similarity	NPD6399	Phase 3
0.7094	Intermediate Similarity	NPD8297	Approved
0.7091	Intermediate Similarity	NPD7638	Approved
0.7064	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5222	Approved
0.7064	Intermediate Similarity	NPD5221	Approved
0.7064	Intermediate Similarity	NPD4697	Phase 3
0.7054	Intermediate Similarity	NPD5211	Phase 2
0.7054	Intermediate Similarity	NPD5224	Approved
0.7054	Intermediate Similarity	NPD5225	Approved
0.7054	Intermediate Similarity	NPD5226	Approved
0.7054	Intermediate Similarity	NPD4633	Approved
0.7043	Intermediate Similarity	NPD6011	Approved
0.7037	Intermediate Similarity	NPD7748	Approved
0.7034	Intermediate Similarity	NPD4632	Approved
0.7027	Intermediate Similarity	NPD7640	Approved
0.7027	Intermediate Similarity	NPD4700	Approved
0.7027	Intermediate Similarity	NPD7639	Approved
0.7019	Intermediate Similarity	NPD3618	Phase 1
0.7009	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD7902	Approved
0.7	Intermediate Similarity	NPD5173	Approved
0.6991	Remote Similarity	NPD5175	Approved
0.6991	Remote Similarity	NPD5174	Approved
0.699	Remote Similarity	NPD4786	Approved
0.6964	Remote Similarity	NPD5223	Approved
0.6942	Remote Similarity	NPD7328	Approved
0.6942	Remote Similarity	NPD7327	Approved
0.6939	Remote Similarity	NPD3703	Phase 2
0.693	Remote Similarity	NPD5141	Approved
0.69	Remote Similarity	NPD6114	Approved
0.69	Remote Similarity	NPD6115	Approved
0.69	Remote Similarity	NPD6118	Approved
0.69	Remote Similarity	NPD6697	Approved
0.6897	Remote Similarity	NPD6686	Approved
0.6885	Remote Similarity	NPD7516	Approved
0.6864	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6411	Approved
0.6847	Remote Similarity	NPD6083	Phase 2
0.6847	Remote Similarity	NPD6084	Phase 2
0.68	Remote Similarity	NPD7604	Phase 2
0.6796	Remote Similarity	NPD3667	Approved
0.6789	Remote Similarity	NPD4202	Approved
0.6777	Remote Similarity	NPD6274	Approved
0.6774	Remote Similarity	NPD8296	Approved
0.6774	Remote Similarity	NPD8380	Approved
0.6774	Remote Similarity	NPD8379	Approved
0.6774	Remote Similarity	NPD5983	Phase 2
0.6774	Remote Similarity	NPD8033	Approved
0.6774	Remote Similarity	NPD8378	Approved
0.6774	Remote Similarity	NPD8335	Approved
0.6765	Remote Similarity	NPD6928	Phase 2
0.6752	Remote Similarity	NPD4730	Approved
0.6752	Remote Similarity	NPD4729	Approved
0.6752	Remote Similarity	NPD5128	Approved
0.6748	Remote Similarity	NPD7100	Approved
0.6748	Remote Similarity	NPD7101	Approved
0.6729	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7900	Approved
0.6727	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4768	Approved
0.6724	Remote Similarity	NPD4767	Approved
0.67	Remote Similarity	NPD6117	Approved
0.6696	Remote Similarity	NPD4754	Approved
0.6694	Remote Similarity	NPD8377	Approved
0.6694	Remote Similarity	NPD8294	Approved
0.6693	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD6067	Discontinued
0.664	Remote Similarity	NPD6921	Approved
0.6639	Remote Similarity	NPD6868	Approved
0.6639	Remote Similarity	NPD5247	Approved
0.6639	Remote Similarity	NPD5250	Approved
0.6639	Remote Similarity	NPD5248	Approved
0.6639	Remote Similarity	NPD5251	Approved
0.6639	Remote Similarity	NPD5249	Phase 3
0.6637	Remote Similarity	NPD5696	Approved
0.6637	Remote Similarity	NPD4225	Approved
0.6636	Remote Similarity	NPD3573	Approved
0.6634	Remote Similarity	NPD6116	Phase 1
0.6633	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7632	Discontinued
0.6585	Remote Similarity	NPD6317	Approved
0.6583	Remote Similarity	NPD5215	Approved
0.6583	Remote Similarity	NPD5217	Approved
0.6583	Remote Similarity	NPD5216	Approved
0.6545	Remote Similarity	NPD7637	Suspended
0.6542	Remote Similarity	NPD6684	Approved
0.6542	Remote Similarity	NPD7521	Approved
0.6542	Remote Similarity	NPD7334	Approved
0.6542	Remote Similarity	NPD7146	Approved
0.6542	Remote Similarity	NPD5330	Approved
0.6542	Remote Similarity	NPD6409	Approved
0.6532	Remote Similarity	NPD6314	Approved
0.6532	Remote Similarity	NPD6313	Approved
0.6518	Remote Similarity	NPD5695	Phase 3
0.6518	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD8513	Phase 3
0.6508	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD8515	Approved
0.6508	Remote Similarity	NPD7503	Approved
0.6508	Remote Similarity	NPD6908	Approved
0.6508	Remote Similarity	NPD8517	Approved
0.6508	Remote Similarity	NPD8516	Approved
0.6508	Remote Similarity	NPD6909	Approved
0.65	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5135	Approved
0.65	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5169	Approved
0.6489	Remote Similarity	NPD5956	Approved
0.6486	Remote Similarity	NPD5778	Approved
0.6486	Remote Similarity	NPD5779	Approved
0.6471	Remote Similarity	NPD5168	Approved
0.6446	Remote Similarity	NPD5127	Approved
0.6442	Remote Similarity	NPD7525	Registered
0.6429	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5282	Discontinued
0.6429	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5737	Approved
0.6422	Remote Similarity	NPD6672	Approved
0.6422	Remote Similarity	NPD6903	Approved
0.6417	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6053	Discontinued
0.6364	Remote Similarity	NPD4245	Approved
0.6364	Remote Similarity	NPD4244	Approved
0.6364	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3668	Phase 3
0.6346	Remote Similarity	NPD7645	Phase 2
0.6339	Remote Similarity	NPD8171	Discontinued
0.6321	Remote Similarity	NPD4221	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