NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	361.19
Volume:	358.732
LogP:	1.149
LogD:	0.909
LogS:	-4.132
# Rotatable Bonds:	0
TPSA:	110.35
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.468
Synthetic Accessibility Score:	7.257
Fsp3:	0.8
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:	-5.167
MDCK Permeability:	8.056174920056947e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.927
Human Intestinal Absorption (HIA):	0.091
20% Bioavailability (F20%):	0.068
30% Bioavailability (F30%):	0.209

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.626
Plasma Protein Binding (PPB):	62.13726043701172%
Volume Distribution (VD):	1.192
Pgp-substrate:	51.56255340576172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.151
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.648
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	3.884
Half-life (T1/2):	0.339

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.468
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.246
Carcinogencity:	0.895
Eye Corrosion:	0.008
Eye Irritation:	0.012
Respiratory Toxicity:	0.993

Download Data

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

Natural Product: NPC477352

Natural Product ID:	NPC477352
*Common Name:**	(1S,2S,5S,8S,9S,10S,11R,15S,18R)-9,10,15,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-azapentacyclo[7.6.2.15,8.01,11.02,8]octadec-16-en-7-one
IUPAC Name:	(1S,2S,5S,8S,9S,10S,11R,15S,18R)-9,10,15,18-tetrahydroxy-12,12-dimethyl-6-methylidene-17-azapentacyclo[7.6.2.15,8.01,11.02,8]octadec-16-en-7-one
Synonyms:
Standard InCHIKey:	FWDMHQLLHQLZSC-XKCURVIJSA-N
Standard InCHI:	InChI=1S/C20H27NO5/c1-9-10-4-5-11-18-8-21-20(26,19(11,14(9)23)15(10)24)16(25)13(18)17(2,3)7-6-12(18)22/h8,10-13,15-16,22,24-26H,1,4-7H2,2-3H3/t10-,11-,12-,13+,15+,16-,18+,19-,20+/m0/s1
SMILES:	CC1(CC[C@@H]([C@]23[C@@H]1[C@@H]([C@@]([C@]45[C@H]2CC[C@H]([C@H]4O)C(=C)C5=O)(N=C3)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118735597
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	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25590529]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28626	Isodon rubescens	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	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000	nM	PMID[25590529]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000	nM	PMID[25590529]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000	nM	PMID[25590529]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000	nM	PMID[25590529]
NPT2	Others	Unspecified		IC50	>	40000	nM	PMID[25590529]

☑ 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 NPC477352 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	154
0.1-0.2	1276
0.2-0.3	6148
0.3-0.4	18327
0.4-0.5	9660
0.5-0.6	6197
0.6-0.7	888
0.7-0.8	46
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7563	Intermediate Similarity	NPC127408
0.7563	Intermediate Similarity	NPC291785
0.7373	Intermediate Similarity	NPC231060
0.7373	Intermediate Similarity	NPC84018
0.7373	Intermediate Similarity	NPC41070
0.7373	Intermediate Similarity	NPC138245
0.735	Intermediate Similarity	NPC181594
0.735	Intermediate Similarity	NPC144739
0.7288	Intermediate Similarity	NPC215271
0.7288	Intermediate Similarity	NPC261333
0.7288	Intermediate Similarity	NPC289539
0.7288	Intermediate Similarity	NPC104371
0.7288	Intermediate Similarity	NPC101233
0.7288	Intermediate Similarity	NPC191094
0.7288	Intermediate Similarity	NPC29247
0.7288	Intermediate Similarity	NPC129004
0.7288	Intermediate Similarity	NPC302008
0.7288	Intermediate Similarity	NPC292374
0.7288	Intermediate Similarity	NPC91772
0.7288	Intermediate Similarity	NPC153775
0.7288	Intermediate Similarity	NPC111524
0.728	Intermediate Similarity	NPC55973
0.7265	Intermediate Similarity	NPC476168
0.7265	Intermediate Similarity	NPC299185
0.7203	Intermediate Similarity	NPC59170
0.72	Intermediate Similarity	NPC67745
0.72	Intermediate Similarity	NPC471461
0.7179	Intermediate Similarity	NPC149761
0.7179	Intermediate Similarity	NPC180849
0.7179	Intermediate Similarity	NPC80401
0.7179	Intermediate Similarity	NPC470378
0.7179	Intermediate Similarity	NPC261994
0.7167	Intermediate Similarity	NPC135548
0.7167	Intermediate Similarity	NPC140242
0.7167	Intermediate Similarity	NPC264979
0.7165	Intermediate Similarity	NPC471093
0.7165	Intermediate Similarity	NPC473324
0.7143	Intermediate Similarity	NPC231278
0.7143	Intermediate Similarity	NPC112895
0.7143	Intermediate Similarity	NPC189663
0.7143	Intermediate Similarity	NPC89860
0.7143	Intermediate Similarity	NPC218123
0.7132	Intermediate Similarity	NPC106479
0.7131	Intermediate Similarity	NPC470388
0.7109	Intermediate Similarity	NPC122339
0.7109	Intermediate Similarity	NPC29505
0.7107	Intermediate Similarity	NPC170978
0.7087	Intermediate Similarity	NPC252679
0.7087	Intermediate Similarity	NPC118721
0.7083	Intermediate Similarity	NPC142352
0.7083	Intermediate Similarity	NPC29112
0.7059	Intermediate Similarity	NPC59350
0.7054	Intermediate Similarity	NPC473303
0.7054	Intermediate Similarity	NPC471245
0.7031	Intermediate Similarity	NPC471476
0.7016	Intermediate Similarity	NPC309388
0.7016	Intermediate Similarity	NPC475803
0.7008	Intermediate Similarity	NPC273155
0.7008	Intermediate Similarity	NPC63841
0.7	Intermediate Similarity	NPC471252
0.7	Intermediate Similarity	NPC64006
0.7	Intermediate Similarity	NPC471248
0.6992	Remote Similarity	NPC156324
0.6992	Remote Similarity	NPC55503
0.6984	Remote Similarity	NPC130511
0.6984	Remote Similarity	NPC307660
0.6977	Remote Similarity	NPC213320
0.6977	Remote Similarity	NPC63244
0.6975	Remote Similarity	NPC278106
0.696	Remote Similarity	NPC277074
0.696	Remote Similarity	NPC87927
0.696	Remote Similarity	NPC209298
0.6953	Remote Similarity	NPC102741
0.6935	Remote Similarity	NPC471790
0.6935	Remote Similarity	NPC163963
0.6935	Remote Similarity	NPC289148
0.6935	Remote Similarity	NPC52899
0.6929	Remote Similarity	NPC166993
0.6929	Remote Similarity	NPC186054
0.6923	Remote Similarity	NPC165895
0.6923	Remote Similarity	NPC471244
0.6923	Remote Similarity	NPC474927
0.6923	Remote Similarity	NPC153604
0.6923	Remote Similarity	NPC473397
0.6923	Remote Similarity	NPC145625
0.6923	Remote Similarity	NPC259009
0.6923	Remote Similarity	NPC174619
0.6923	Remote Similarity	NPC473352
0.6917	Remote Similarity	NPC472496
0.6905	Remote Similarity	NPC13149
0.6885	Remote Similarity	NPC13949
0.688	Remote Similarity	NPC214946
0.688	Remote Similarity	NPC76866
0.688	Remote Similarity	NPC88203
0.688	Remote Similarity	NPC304832
0.688	Remote Similarity	NPC272472
0.688	Remote Similarity	NPC148628
0.688	Remote Similarity	NPC246736
0.688	Remote Similarity	NPC286519
0.6875	Remote Similarity	NPC469984
0.6875	Remote Similarity	NPC471094
0.6875	Remote Similarity	NPC469733
0.6875	Remote Similarity	NPC469729
0.6875	Remote Similarity	NPC473410
0.687	Remote Similarity	NPC132668
0.687	Remote Similarity	NPC94141
0.686	Remote Similarity	NPC280804
0.6855	Remote Similarity	NPC287676
0.685	Remote Similarity	NPC4115
0.685	Remote Similarity	NPC12823
0.685	Remote Similarity	NPC200957
0.685	Remote Similarity	NPC138908
0.6846	Remote Similarity	NPC471243
0.6842	Remote Similarity	NPC473304
0.6833	Remote Similarity	NPC198242
0.6833	Remote Similarity	NPC211403
0.6825	Remote Similarity	NPC216114
0.6825	Remote Similarity	NPC122811
0.6825	Remote Similarity	NPC139347
0.6818	Remote Similarity	NPC17165
0.6818	Remote Similarity	NPC243354
0.6809	Remote Similarity	NPC139585
0.68	Remote Similarity	NPC46848
0.68	Remote Similarity	NPC60947
0.68	Remote Similarity	NPC14634
0.6797	Remote Similarity	NPC475800
0.6797	Remote Similarity	NPC469746
0.6797	Remote Similarity	NPC471474
0.6794	Remote Similarity	NPC157929
0.6777	Remote Similarity	NPC82138
0.6774	Remote Similarity	NPC78427
0.6774	Remote Similarity	NPC471038
0.6774	Remote Similarity	NPC16911
0.6772	Remote Similarity	NPC98603
0.6772	Remote Similarity	NPC202793
0.6772	Remote Similarity	NPC84928
0.6772	Remote Similarity	NPC474558
0.6772	Remote Similarity	NPC301787
0.6769	Remote Similarity	NPC85391
0.6769	Remote Similarity	NPC320383
0.6769	Remote Similarity	NPC474786
0.6769	Remote Similarity	NPC137104
0.6767	Remote Similarity	NPC88945
0.6767	Remote Similarity	NPC229752
0.6752	Remote Similarity	NPC102292
0.6752	Remote Similarity	NPC471034
0.6752	Remote Similarity	NPC190704
0.675	Remote Similarity	NPC100313
0.6748	Remote Similarity	NPC104568
0.6746	Remote Similarity	NPC275990
0.6744	Remote Similarity	NPC9013
0.6721	Remote Similarity	NPC470385
0.6721	Remote Similarity	NPC470386
0.6719	Remote Similarity	NPC222833
0.6719	Remote Similarity	NPC56656
0.6718	Remote Similarity	NPC94650
0.6718	Remote Similarity	NPC329953
0.6716	Remote Similarity	NPC78836
0.6694	Remote Similarity	NPC10864
0.6692	Remote Similarity	NPC474725
0.6692	Remote Similarity	NPC469744
0.6692	Remote Similarity	NPC274827
0.6692	Remote Similarity	NPC131903
0.6667	Remote Similarity	NPC210214
0.6667	Remote Similarity	NPC252614
0.6667	Remote Similarity	NPC98639
0.6667	Remote Similarity	NPC470232
0.6667	Remote Similarity	NPC146683
0.6667	Remote Similarity	NPC124358
0.6667	Remote Similarity	NPC169375
0.6644	Remote Similarity	NPC141669
0.664	Remote Similarity	NPC89099
0.664	Remote Similarity	NPC98837
0.664	Remote Similarity	NPC20479
0.664	Remote Similarity	NPC474793
0.664	Remote Similarity	NPC109059
0.664	Remote Similarity	NPC288
0.664	Remote Similarity	NPC28864
0.664	Remote Similarity	NPC38296
0.664	Remote Similarity	NPC38471
0.664	Remote Similarity	NPC162459
0.6621	Remote Similarity	NPC145899
0.6617	Remote Similarity	NPC194273
0.6615	Remote Similarity	NPC211224
0.6614	Remote Similarity	NPC476755
0.6613	Remote Similarity	NPC200054
0.6613	Remote Similarity	NPC29410
0.6613	Remote Similarity	NPC470387
0.6613	Remote Similarity	NPC329910
0.6597	Remote Similarity	NPC76999
0.6591	Remote Similarity	NPC56025
0.6589	Remote Similarity	NPC37600
0.6587	Remote Similarity	NPC293866
0.6585	Remote Similarity	NPC277399
0.6585	Remote Similarity	NPC475118
0.6581	Remote Similarity	NPC118800
0.6581	Remote Similarity	NPC291320
0.6581	Remote Similarity	NPC471036
0.6562	Remote Similarity	NPC266
0.6562	Remote Similarity	NPC159442

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 NPC477352 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	117
0.1-0.2	891
0.2-0.3	3981
0.3-0.4	3177
0.4-0.5	679
0.5-0.6	295
0.6-0.7	10
0.7-0.8	0
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
0.672	Remote Similarity	NPD8418	Phase 2
0.6644	Remote Similarity	NPD6333	Approved
0.6644	Remote Similarity	NPD6334	Approved
0.6515	Remote Similarity	NPD4634	Approved
0.6286	Remote Similarity	NPD6921	Approved
0.6202	Remote Similarity	NPD5286	Approved
0.6202	Remote Similarity	NPD4696	Approved
0.6202	Remote Similarity	NPD5285	Approved
0.6172	Remote Similarity	NPD4755	Approved
0.6107	Remote Similarity	NPD5224	Approved
0.6107	Remote Similarity	NPD5211	Phase 2
0.6107	Remote Similarity	NPD5225	Approved
0.6107	Remote Similarity	NPD4633	Approved
0.6107	Remote Similarity	NPD5226	Approved
0.6099	Remote Similarity	NPD6319	Approved
0.6077	Remote Similarity	NPD4700	Approved
0.6061	Remote Similarity	NPD5174	Approved
0.6061	Remote Similarity	NPD5175	Approved
0.6056	Remote Similarity	NPD6909	Approved
0.6056	Remote Similarity	NPD6908	Approved
0.6032	Remote Similarity	NPD6079	Approved
0.6031	Remote Similarity	NPD5223	Approved
0.6015	Remote Similarity	NPD5141	Approved
0.6014	Remote Similarity	NPD8298	Phase 2
0.6014	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD7115	Discovery
0.5986	Remote Similarity	NPD6054	Approved
0.5969	Remote Similarity	NPD5221	Approved
0.5969	Remote Similarity	NPD5222	Approved
0.5969	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD4697	Phase 3
0.5944	Remote Similarity	NPD6016	Approved
0.5944	Remote Similarity	NPD6015	Approved
0.5935	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5697	Approved
0.5923	Remote Similarity	NPD5173	Approved
0.5918	Remote Similarity	NPD7736	Approved
0.5906	Remote Similarity	NPD8035	Phase 2
0.5906	Remote Similarity	NPD8034	Phase 2
0.5903	Remote Similarity	NPD5988	Approved
0.5903	Remote Similarity	NPD6370	Approved
0.5902	Remote Similarity	NPD4788	Approved
0.5887	Remote Similarity	NPD3618	Phase 1
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD4730	Approved
0.5882	Remote Similarity	NPD6899	Approved
0.5882	Remote Similarity	NPD8174	Phase 2
0.5882	Remote Similarity	NPD4729	Approved
0.5882	Remote Similarity	NPD5128	Approved
0.5882	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD6059	Approved
0.587	Remote Similarity	NPD6649	Approved
0.587	Remote Similarity	NPD6650	Approved
0.5862	Remote Similarity	NPD7604	Phase 2
0.5859	Remote Similarity	NPD4202	Approved
0.5852	Remote Similarity	NPD5739	Approved
0.5852	Remote Similarity	NPD4767	Approved
0.5852	Remote Similarity	NPD6920	Discontinued
0.5852	Remote Similarity	NPD4768	Approved
0.5852	Remote Similarity	NPD6402	Approved
0.5852	Remote Similarity	NPD7128	Approved
0.5852	Remote Similarity	NPD6675	Approved
0.5839	Remote Similarity	NPD6372	Approved
0.5839	Remote Similarity	NPD6013	Approved
0.5839	Remote Similarity	NPD6014	Approved
0.5839	Remote Similarity	NPD6373	Approved
0.5839	Remote Similarity	NPD6012	Approved
0.5827	Remote Similarity	NPD8297	Approved
0.5822	Remote Similarity	NPD7492	Approved
0.5821	Remote Similarity	NPD4754	Approved
0.5809	Remote Similarity	NPD5701	Approved
0.5797	Remote Similarity	NPD5247	Approved
0.5797	Remote Similarity	NPD5249	Phase 3
0.5797	Remote Similarity	NPD5250	Approved
0.5797	Remote Similarity	NPD7290	Approved
0.5797	Remote Similarity	NPD5251	Approved
0.5797	Remote Similarity	NPD6883	Approved
0.5797	Remote Similarity	NPD7102	Approved
0.5797	Remote Similarity	NPD5248	Approved
0.5782	Remote Similarity	NPD6616	Approved
0.5775	Remote Similarity	NPD6009	Approved
0.5772	Remote Similarity	NPD7319	Approved
0.5766	Remote Similarity	NPD7320	Approved
0.5766	Remote Similarity	NPD6011	Approved
0.5763	Remote Similarity	NPD3703	Phase 2
0.576	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5215	Approved
0.5755	Remote Similarity	NPD8130	Phase 1
0.5755	Remote Similarity	NPD5216	Approved
0.5755	Remote Similarity	NPD6869	Approved
0.5755	Remote Similarity	NPD6617	Approved
0.5755	Remote Similarity	NPD5217	Approved
0.5755	Remote Similarity	NPD6847	Approved
0.5753	Remote Similarity	NPD8328	Phase 3
0.5743	Remote Similarity	NPD7078	Approved
0.5735	Remote Similarity	NPD6008	Approved
0.5733	Remote Similarity	NPD6914	Discontinued
0.5726	Remote Similarity	NPD4786	Approved
0.5714	Remote Similarity	NPD6882	Approved
0.5704	Remote Similarity	NPD6940	Discontinued
0.5693	Remote Similarity	NPD6412	Phase 2
0.5692	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD3667	Approved
0.5683	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5683	Remote Similarity	NPD5169	Approved
0.5683	Remote Similarity	NPD5135	Approved
0.5676	Remote Similarity	NPD7507	Approved
0.5664	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD7515	Phase 2
0.5655	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.5655	Remote Similarity	NPD7147	Phase 3
0.5652	Remote Similarity	NPD6415	Discontinued
0.5649	Remote Similarity	NPD4629	Approved
0.5649	Remote Similarity	NPD5210	Approved
0.5643	Remote Similarity	NPD5127	Approved
0.5638	Remote Similarity	NPD8293	Discontinued
0.5625	Remote Similarity	NPD4753	Phase 2
0.5616	Remote Similarity	NPD5983	Phase 2
0.5615	Remote Similarity	NPD6399	Phase 3
0.56	Remote Similarity	NPD3666	Approved
0.56	Remote Similarity	NPD3133	Approved
0.56	Remote Similarity	NPD3665	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