NPASS Compound

Structure

NPC469729 OpenBabel07101719522D 26 30 0 0 1 0 0 0 0 0999 V2000 2.1739 -1.2121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3465 1.8521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3083 1.8377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3916 -2.7722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3991 -0.0359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4095 0.6567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7942 -0.3732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2089 -1.5423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6153 1.0299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2591 -0.9148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4809 -1.4802 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6876 -1.0416 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2099 0.6746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0104 0.6926 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5946 -0.3553 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9619 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2972 -0.9148 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5946 -0.3553 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8149 1.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1996 -0.0179 0.0000 C 0 0 2 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 -1.6024 -1.3389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5273 0.7782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2121 -1.2121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5658 -2.2788 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 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 19 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 8 1 6 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 6 0 0 0 13 19 1 0 0 0 0 13 20 1 1 0 0 0 14 21 1 0 0 0 0 14 26 1 6 0 0 0 15 20 1 1 0 0 0 15 21 1 0 0 0 0 16 23 2 0 0 0 0 17 21 1 1 0 0 0 17 24 1 0 0 0 0 18 20 1 6 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 20 7 1 6 0 0 0 21 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.21
Volume:	367.668
LogP:	1.983
LogD:	2.444
LogS:	-4.509
# Rotatable Bonds:	1
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.699
Synthetic Accessibility Score:	7.021
Fsp3:	0.857
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:	-4.931
MDCK Permeability:	1.3254142686491832e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.966
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.664
Plasma Protein Binding (PPB):	51.91961669921875%
Volume Distribution (VD):	1.108
Pgp-substrate:	65.57872009277344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.775
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.197
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.212

ADMET: Excretion

Clearance (CL):	4.744
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.213
Drug-inuced Liver Injury (DILI):	0.063
AMES Toxicity:	0.302
Rat Oral Acute Toxicity:	0.87
Maximum Recommended Daily Dose:	0.827
Skin Sensitization:	0.542
Carcinogencity:	0.539
Eye Corrosion:	0.094
Eye Irritation:	0.02
Respiratory Toxicity:	0.99

Download Data

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

Natural Product: NPC469729

Natural Product ID:	NPC469729
*Common Name:**	DZEDOCQBLMZSHN-WPHQSEFKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DZEDOCQBLMZSHN-WPHQSEFKSA-N
Standard InCHI:	InChI=1S/C21H30O5/c1-10-11-8-12(22)15-20-7-5-6-19(2,3)13(20)9-14(26-18(20)25-4)21(15,16(10)23)17(11)24/h11-15,17-18,22,24H,1,5-9H2,2-4H3/t11-,12-,13+,14-,15-,17+,18-,20-,21+/m0/s1
SMILES:	CC1(CCCC23C1CC(C45C2C(CC(C4O)C(=C)C5=O)O)OC3OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1163894
PubChem CID:	46906463
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
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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	950.0	nM	PMID[460844]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	3300.0	nM	PMID[460844]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	4400.0	nM	PMID[460844]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5600.0	nM	PMID[460844]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	9800.0	nM	PMID[460844]

☑ 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 NPC469729 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	291
0.1-0.2	2098
0.2-0.3	6586
0.3-0.4	11192
0.4-0.5	10006
0.5-0.6	5994
0.6-0.7	3941
0.7-0.8	2203
0.8-0.85	296
0.85-0.9	38
0.9-0.95	38
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469733
0.9798	High Similarity	NPC12823
0.9706	High Similarity	NPC329953
0.9703	High Similarity	NPC469744
0.97	High Similarity	NPC469746
0.9612	High Similarity	NPC473303
0.9515	High Similarity	NPC122339
0.9495	High Similarity	NPC309388
0.9495	High Similarity	NPC475803
0.9423	High Similarity	NPC471245
0.9417	High Similarity	NPC473324
0.9406	High Similarity	NPC4115
0.9327	High Similarity	NPC63244
0.9307	High Similarity	NPC13149
0.9252	High Similarity	NPC473304
0.9245	High Similarity	NPC17165
0.9238	High Similarity	NPC471244
0.9238	High Similarity	NPC145625
0.9231	High Similarity	NPC471476
0.9223	High Similarity	NPC55973
0.9208	High Similarity	NPC139347
0.92	High Similarity	NPC14634
0.9151	High Similarity	NPC471248
0.9151	High Similarity	NPC94141
0.9143	High Similarity	NPC29505
0.9135	High Similarity	NPC252679
0.9135	High Similarity	NPC118721
0.9126	High Similarity	NPC471461
0.9126	High Similarity	NPC67745
0.9118	High Similarity	NPC202793
0.9074	High Similarity	NPC78836
0.9057	High Similarity	NPC157929
0.9048	High Similarity	NPC471093
0.9038	High Similarity	NPC89860
0.9038	High Similarity	NPC189663
0.9038	High Similarity	NPC232133
0.902	High Similarity	NPC87927
0.901	High Similarity	NPC471790
0.8981	High Similarity	NPC88945
0.8981	High Similarity	NPC229752
0.8972	High Similarity	NPC132668
0.8972	High Similarity	NPC471252
0.8952	High Similarity	NPC469983
0.8942	High Similarity	NPC96333
0.8942	High Similarity	NPC88833
0.8889	High Similarity	NPC84018
0.8889	High Similarity	NPC138245
0.8889	High Similarity	NPC231060
0.8879	High Similarity	NPC473397
0.8868	High Similarity	NPC98069
0.8868	High Similarity	NPC49730
0.8857	High Similarity	NPC63841
0.8846	High Similarity	NPC307660
0.8846	High Similarity	NPC103172
0.8846	High Similarity	NPC130511
0.8846	High Similarity	NPC164600
0.8824	High Similarity	NPC52899
0.8824	High Similarity	NPC163963
0.8824	High Similarity	NPC289148
0.8788	High Similarity	NPC302008
0.8788	High Similarity	NPC191094
0.8785	High Similarity	NPC213320
0.8774	High Similarity	NPC102741
0.8762	High Similarity	NPC61071
0.8762	High Similarity	NPC186054
0.875	High Similarity	NPC474558
0.875	High Similarity	NPC101842
0.8738	High Similarity	NPC246736
0.8738	High Similarity	NPC148628
0.8738	High Similarity	NPC286519
0.8738	High Similarity	NPC304832
0.8738	High Similarity	NPC88203
0.8738	High Similarity	NPC76866
0.8738	High Similarity	NPC214946
0.8725	High Similarity	NPC287676
0.8704	High Similarity	NPC473352
0.8704	High Similarity	NPC474927
0.8687	High Similarity	NPC144739
0.8687	High Similarity	NPC59170
0.8687	High Similarity	NPC181594
0.8679	High Similarity	NPC469984
0.8679	High Similarity	NPC231278
0.8679	High Similarity	NPC471094
0.8679	High Similarity	NPC112895
0.8679	High Similarity	NPC473410
0.8679	High Similarity	NPC218123
0.8654	High Similarity	NPC216114
0.8641	High Similarity	NPC46848
0.8627	High Similarity	NPC78427
0.8627	High Similarity	NPC16911
0.8627	High Similarity	NPC471038
0.8627	High Similarity	NPC474793
0.8614	High Similarity	NPC13949
0.8611	High Similarity	NPC471243
0.86	High Similarity	NPC289539
0.86	High Similarity	NPC261333
0.86	High Similarity	NPC91772
0.86	High Similarity	NPC111524
0.86	High Similarity	NPC104371
0.86	High Similarity	NPC29247
0.86	High Similarity	NPC101233
0.86	High Similarity	NPC129004
0.86	High Similarity	NPC292374
0.86	High Similarity	NPC153775
0.86	High Similarity	NPC215271
0.8598	High Similarity	NPC8431
0.8586	High Similarity	NPC476168
0.8586	High Similarity	NPC299185
0.8585	High Similarity	NPC471474
0.8571	High Similarity	NPC98603
0.8571	High Similarity	NPC84928
0.8558	High Similarity	NPC275990
0.8545	High Similarity	NPC243354
0.8544	High Similarity	NPC291785
0.8544	High Similarity	NPC127408
0.8519	High Similarity	NPC320383
0.8519	High Similarity	NPC85391
0.8519	High Similarity	NPC98633
0.8519	High Similarity	NPC474786
0.8519	High Similarity	NPC137104
0.8519	High Similarity	NPC130302
0.8515	High Similarity	NPC470232
0.8515	High Similarity	NPC29112
0.8491	Intermediate Similarity	NPC56656
0.8491	Intermediate Similarity	NPC285927
0.8485	Intermediate Similarity	NPC261994
0.8485	Intermediate Similarity	NPC470378
0.8485	Intermediate Similarity	NPC180849
0.8485	Intermediate Similarity	NPC149761
0.8485	Intermediate Similarity	NPC80401
0.8476	Intermediate Similarity	NPC96217
0.8462	Intermediate Similarity	NPC148279
0.8462	Intermediate Similarity	NPC236585
0.8455	Intermediate Similarity	NPC73986
0.8447	Intermediate Similarity	NPC28864
0.8447	Intermediate Similarity	NPC89099
0.8447	Intermediate Similarity	NPC20479
0.8447	Intermediate Similarity	NPC38471
0.8447	Intermediate Similarity	NPC162459
0.8447	Intermediate Similarity	NPC38296
0.8447	Intermediate Similarity	NPC98837
0.844	Intermediate Similarity	NPC274833
0.844	Intermediate Similarity	NPC471251
0.8431	Intermediate Similarity	NPC264979
0.8431	Intermediate Similarity	NPC135548
0.8431	Intermediate Similarity	NPC140242
0.8431	Intermediate Similarity	NPC329910
0.8431	Intermediate Similarity	NPC29410
0.8431	Intermediate Similarity	NPC200054
0.8426	Intermediate Similarity	NPC274827
0.8426	Intermediate Similarity	NPC131903
0.8426	Intermediate Similarity	NPC471250
0.8416	Intermediate Similarity	NPC470386
0.8416	Intermediate Similarity	NPC470385
0.8416	Intermediate Similarity	NPC475118
0.84	Intermediate Similarity	NPC278106
0.8396	Intermediate Similarity	NPC244247
0.8365	Intermediate Similarity	NPC267921
0.8365	Intermediate Similarity	NPC470388
0.8365	Intermediate Similarity	NPC293866
0.8364	Intermediate Similarity	NPC472719
0.8364	Intermediate Similarity	NPC207845
0.835	Intermediate Similarity	NPC10864
0.8349	Intermediate Similarity	NPC124053
0.8349	Intermediate Similarity	NPC255655
0.8333	Intermediate Similarity	NPC273155
0.8333	Intermediate Similarity	NPC470229
0.8333	Intermediate Similarity	NPC98639
0.8333	Intermediate Similarity	NPC210214
0.8318	Intermediate Similarity	NPC138908
0.8318	Intermediate Similarity	NPC37600
0.8318	Intermediate Similarity	NPC200957
0.8317	Intermediate Similarity	NPC59350
0.8302	Intermediate Similarity	NPC122811
0.8302	Intermediate Similarity	NPC277074
0.8302	Intermediate Similarity	NPC159442
0.8302	Intermediate Similarity	NPC266
0.8302	Intermediate Similarity	NPC209298
0.8288	Intermediate Similarity	NPC285086
0.8288	Intermediate Similarity	NPC194273
0.8273	Intermediate Similarity	NPC270586
0.8273	Intermediate Similarity	NPC56025
0.8269	Intermediate Similarity	NPC288
0.8269	Intermediate Similarity	NPC26270
0.8269	Intermediate Similarity	NPC109059
0.8252	Intermediate Similarity	NPC470387
0.8241	Intermediate Similarity	NPC201908
0.8241	Intermediate Similarity	NPC166993
0.8241	Intermediate Similarity	NPC176949
0.8235	Intermediate Similarity	NPC64006
0.8235	Intermediate Similarity	NPC47853
0.8224	Intermediate Similarity	NPC96268
0.8218	Intermediate Similarity	NPC211403
0.8218	Intermediate Similarity	NPC198242
0.8218	Intermediate Similarity	NPC250753
0.8208	Intermediate Similarity	NPC272472
0.8198	Intermediate Similarity	NPC243572
0.819	Intermediate Similarity	NPC55503
0.819	Intermediate Similarity	NPC156324
0.8182	Intermediate Similarity	NPC259009

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 NPC469729 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	2457
0.2-0.3	4068
0.3-0.4	1482
0.4-0.5	428
0.5-0.6	237
0.6-0.7	157
0.7-0.8	33
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
0.7881	Intermediate Similarity	NPD6370	Approved
0.7851	Intermediate Similarity	NPD7736	Approved
0.7748	Intermediate Similarity	NPD6412	Phase 2
0.7712	Intermediate Similarity	NPD6054	Approved
0.7667	Intermediate Similarity	NPD8328	Phase 3
0.7647	Intermediate Similarity	NPD6016	Approved
0.7647	Intermediate Similarity	NPD6015	Approved
0.7642	Intermediate Similarity	NPD7319	Approved
0.7607	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD5988	Approved
0.7563	Intermediate Similarity	NPD6059	Approved
0.7541	Intermediate Similarity	NPD7507	Approved
0.75	Intermediate Similarity	NPD8133	Approved
0.748	Intermediate Similarity	NPD8293	Discontinued
0.7459	Intermediate Similarity	NPD7492	Approved
0.7414	Intermediate Similarity	NPD6882	Approved
0.7411	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6616	Approved
0.7358	Intermediate Similarity	NPD8034	Phase 2
0.7358	Intermediate Similarity	NPD8035	Phase 2
0.7339	Intermediate Similarity	NPD7078	Approved
0.7311	Intermediate Similarity	NPD6009	Approved
0.7304	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5697	Approved
0.7273	Intermediate Similarity	NPD6319	Approved
0.7241	Intermediate Similarity	NPD4634	Approved
0.7217	Intermediate Similarity	NPD6881	Approved
0.7217	Intermediate Similarity	NPD6899	Approved
0.7217	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4696	Approved
0.7207	Intermediate Similarity	NPD5286	Approved
0.7207	Intermediate Similarity	NPD5285	Approved
0.7193	Intermediate Similarity	NPD6675	Approved
0.7193	Intermediate Similarity	NPD6008	Approved
0.7193	Intermediate Similarity	NPD7128	Approved
0.7193	Intermediate Similarity	NPD6402	Approved
0.7193	Intermediate Similarity	NPD5739	Approved
0.7182	Intermediate Similarity	NPD4755	Approved
0.7179	Intermediate Similarity	NPD6650	Approved
0.7179	Intermediate Similarity	NPD6649	Approved
0.7155	Intermediate Similarity	NPD6012	Approved
0.7155	Intermediate Similarity	NPD6373	Approved
0.7155	Intermediate Similarity	NPD6372	Approved
0.7155	Intermediate Similarity	NPD6013	Approved
0.7155	Intermediate Similarity	NPD6014	Approved
0.713	Intermediate Similarity	NPD5701	Approved
0.7115	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7328	Approved
0.7107	Intermediate Similarity	NPD7327	Approved
0.7094	Intermediate Similarity	NPD6883	Approved
0.7094	Intermediate Similarity	NPD7102	Approved
0.7094	Intermediate Similarity	NPD7290	Approved
0.708	Intermediate Similarity	NPD4633	Approved
0.708	Intermediate Similarity	NPD5225	Approved
0.708	Intermediate Similarity	NPD5224	Approved
0.708	Intermediate Similarity	NPD5226	Approved
0.708	Intermediate Similarity	NPD5211	Phase 2
0.7069	Intermediate Similarity	NPD7320	Approved
0.7069	Intermediate Similarity	NPD6686	Approved
0.7069	Intermediate Similarity	NPD6011	Approved
0.7059	Intermediate Similarity	NPD4632	Approved
0.7054	Intermediate Similarity	NPD4700	Approved
0.7049	Intermediate Similarity	NPD7516	Approved
0.7037	Intermediate Similarity	NPD6079	Approved
0.7034	Intermediate Similarity	NPD8130	Phase 1
0.7034	Intermediate Similarity	NPD6617	Approved
0.7034	Intermediate Similarity	NPD6869	Approved
0.7034	Intermediate Similarity	NPD6847	Approved
0.7018	Intermediate Similarity	NPD5174	Approved
0.7018	Intermediate Similarity	NPD5175	Approved
0.7009	Intermediate Similarity	NPD5328	Approved
0.7008	Intermediate Similarity	NPD6033	Approved
0.6991	Remote Similarity	NPD5223	Approved
0.6975	Remote Similarity	NPD8297	Approved
0.6972	Remote Similarity	NPD6399	Phase 3
0.6957	Remote Similarity	NPD5141	Approved
0.6937	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5221	Approved
0.6937	Remote Similarity	NPD5222	Approved
0.6937	Remote Similarity	NPD4697	Phase 3
0.6935	Remote Similarity	NPD8033	Approved
0.6923	Remote Similarity	NPD4788	Approved
0.6887	Remote Similarity	NPD3618	Phase 1
0.6885	Remote Similarity	NPD7115	Discovery
0.6875	Remote Similarity	NPD7902	Approved
0.6875	Remote Similarity	NPD5173	Approved
0.6855	Remote Similarity	NPD8377	Approved
0.6855	Remote Similarity	NPD8294	Approved
0.6825	Remote Similarity	NPD6067	Discontinued
0.6818	Remote Similarity	NPD4202	Approved
0.6814	Remote Similarity	NPD7638	Approved
0.6803	Remote Similarity	NPD6274	Approved
0.68	Remote Similarity	NPD8380	Approved
0.68	Remote Similarity	NPD8379	Approved
0.68	Remote Similarity	NPD5983	Phase 2
0.68	Remote Similarity	NPD8335	Approved
0.68	Remote Similarity	NPD8378	Approved
0.68	Remote Similarity	NPD8296	Approved
0.68	Remote Similarity	NPD3703	Phase 2
0.678	Remote Similarity	NPD4729	Approved
0.678	Remote Similarity	NPD4730	Approved
0.678	Remote Similarity	NPD5128	Approved
0.6757	Remote Similarity	NPD7748	Approved
0.6754	Remote Similarity	NPD7639	Approved
0.6754	Remote Similarity	NPD7640	Approved
0.6752	Remote Similarity	NPD4767	Approved
0.6752	Remote Similarity	NPD4768	Approved
0.675	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7515	Phase 2
0.6724	Remote Similarity	NPD4754	Approved
0.6698	Remote Similarity	NPD4786	Approved
0.6693	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.664	Remote Similarity	NPD7100	Approved
0.664	Remote Similarity	NPD7101	Approved
0.6635	Remote Similarity	NPD6928	Phase 2
0.6613	Remote Similarity	NPD6317	Approved
0.6612	Remote Similarity	NPD5217	Approved
0.6612	Remote Similarity	NPD5216	Approved
0.6612	Remote Similarity	NPD5215	Approved
0.6607	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7900	Approved
0.6602	Remote Similarity	NPD6118	Approved
0.6602	Remote Similarity	NPD6114	Approved
0.6602	Remote Similarity	NPD6115	Approved
0.6602	Remote Similarity	NPD6697	Approved
0.6589	Remote Similarity	NPD6336	Discontinued
0.6579	Remote Similarity	NPD6084	Phase 2
0.6579	Remote Similarity	NPD6083	Phase 2
0.6577	Remote Similarity	NPD6411	Approved
0.656	Remote Similarity	NPD6313	Approved
0.656	Remote Similarity	NPD6335	Approved
0.656	Remote Similarity	NPD6314	Approved
0.6549	Remote Similarity	NPD4629	Approved
0.6549	Remote Similarity	NPD5210	Approved
0.6545	Remote Similarity	NPD4753	Phase 2
0.6542	Remote Similarity	NPD3666	Approved
0.6542	Remote Similarity	NPD3133	Approved
0.6542	Remote Similarity	NPD3665	Phase 1
0.6535	Remote Similarity	NPD6921	Approved
0.6535	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5135	Approved
0.6529	Remote Similarity	NPD5169	Approved
0.6529	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5696	Approved
0.6522	Remote Similarity	NPD4225	Approved
0.6518	Remote Similarity	NPD8171	Discontinued
0.6515	Remote Similarity	NPD5956	Approved
0.6514	Remote Similarity	NPD3573	Approved
0.6505	Remote Similarity	NPD6116	Phase 1
0.6475	Remote Similarity	NPD5127	Approved
0.646	Remote Similarity	NPD5282	Discontinued
0.6455	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6117	Approved
0.6406	Remote Similarity	NPD6909	Approved
0.6406	Remote Similarity	NPD6908	Approved
0.6404	Remote Similarity	NPD5695	Phase 3
0.64	Remote Similarity	NPD6868	Approved
0.6396	Remote Similarity	NPD6101	Approved
0.6396	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5168	Approved
0.6356	Remote Similarity	NPD7632	Discontinued
0.6337	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7525	Registered
0.632	Remote Similarity	NPD5167	Approved
0.6304	Remote Similarity	NPD6334	Approved
0.6304	Remote Similarity	NPD6333	Approved
0.63	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6053	Discontinued
0.6273	Remote Similarity	NPD7146	Approved
0.6273	Remote Similarity	NPD7521	Approved
0.6273	Remote Similarity	NPD5330	Approved
0.6273	Remote Similarity	NPD6684	Approved
0.6273	Remote Similarity	NPD6409	Approved
0.6273	Remote Similarity	NPD7334	Approved
0.6271	Remote Similarity	NPD1700	Approved
0.627	Remote Similarity	NPD6940	Discontinued
0.6261	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD3668	Phase 3
0.6228	Remote Similarity	NPD5779	Approved
0.6228	Remote Similarity	NPD5778	Approved
0.6214	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4221	Approved
0.6204	Remote Similarity	NPD4223	Phase 3

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