NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	372.19
Volume:	385.611
LogP:	3.231
LogD:	2.52
LogS:	-4.389
# Rotatable Bonds:	3
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	6.363
Fsp3:	0.682
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.825
MDCK Permeability:	5.4753862059442326e-05
Pgp-inhibitor:	0.509
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.666
Plasma Protein Binding (PPB):	63.400726318359375%
Volume Distribution (VD):	1.116
Pgp-substrate:	51.462711334228516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.135
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.462
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.764
CYP3A4-substrate:	0.393

ADMET: Excretion

Clearance (CL):	5.623
Half-life (T1/2):	0.087

ADMET: Toxicity

hERG Blockers:	0.475
Human Hepatotoxicity (H-HT):	0.497
Drug-inuced Liver Injury (DILI):	0.504
AMES Toxicity:	0.145
Rat Oral Acute Toxicity:	0.933
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.595
Carcinogencity:	0.902
Eye Corrosion:	0.02
Eye Irritation:	0.031
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC476934

Natural Product ID:	NPC476934
*Common Name:**	Crotobarin
IUPAC Name:	[(1S,4S,5S,10S,12R,14S)-5-methyl-16-methylidene-8,15-dioxo-4-prop-1-en-2-yl-9-oxatetracyclo[10.2.2.01,10.05,10]hexadecan-14-yl] acetate
Synonyms:	Crotobarin
Standard InCHIKey:	GTSBYDSLDSOPCU-RUNIHDHWSA-N
Standard InCHI:	InChI=1S/C22H28O5/c1-12(2)16-6-9-21-17(26-14(4)23)10-15(13(3)19(21)25)11-22(21)20(16,5)8-7-18(24)27-22/h15-17H,1,3,6-11H2,2,4-5H3/t15-,16+,17+,20+,21-,22+/m1/s1
SMILES:	CC(=C)[C@@H]1CC[C@]23[C@H](C[C@H](C[C@]24[C@]1(CCC(=O)O4)C)C(=C)C3=O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	52941017
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO33518	Croton goudotii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20849074]
NPO33570	Croton barorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20849074]

☑ 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	4
Others	3

Activity Type	# Activity
Cell Line	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	Activity	=	25.7	%	PMID[20849074]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	12.3	%	PMID[20849074]
NPT111	Cell Line	K562	Homo sapiens	Activity	=	56.5	%	PMID[20849074]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2500	nM	PMID[20849074]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	2100	nM	PMID[20849074]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	790	nM	PMID[20849074]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	560	nM	PMID[20849074]

☑ 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 NPC476934 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	297
0.1-0.2	2350
0.2-0.3	6819
0.3-0.4	12153
0.4-0.5	9672
0.5-0.6	6519
0.6-0.7	3330
0.7-0.8	1497
0.8-0.85	54
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8941	High Similarity	NPC476935
0.8889	High Similarity	NPC470230
0.8696	High Similarity	NPC475118
0.8667	High Similarity	NPC471043
0.8617	High Similarity	NPC96839
0.8602	High Similarity	NPC470232
0.8602	High Similarity	NPC470229
0.8557	High Similarity	NPC139347
0.8542	High Similarity	NPC46848
0.8526	High Similarity	NPC474793
0.8511	High Similarity	NPC329910
0.8495	Intermediate Similarity	NPC470385
0.8495	Intermediate Similarity	NPC469982
0.8495	Intermediate Similarity	NPC470386
0.8454	Intermediate Similarity	NPC275990
0.8454	Intermediate Similarity	NPC76866
0.8454	Intermediate Similarity	NPC148628
0.8454	Intermediate Similarity	NPC246736
0.8454	Intermediate Similarity	NPC286519
0.8454	Intermediate Similarity	NPC214946
0.8454	Intermediate Similarity	NPC304832
0.8454	Intermediate Similarity	NPC88203
0.8404	Intermediate Similarity	NPC217329
0.8351	Intermediate Similarity	NPC289148
0.8351	Intermediate Similarity	NPC236585
0.8351	Intermediate Similarity	NPC163963
0.8351	Intermediate Similarity	NPC52899
0.8333	Intermediate Similarity	NPC89099
0.8333	Intermediate Similarity	NPC28864
0.8333	Intermediate Similarity	NPC20479
0.8333	Intermediate Similarity	NPC162459
0.8333	Intermediate Similarity	NPC471038
0.8333	Intermediate Similarity	NPC38471
0.8333	Intermediate Similarity	NPC98837
0.8333	Intermediate Similarity	NPC471042
0.8333	Intermediate Similarity	NPC38296
0.8316	Intermediate Similarity	NPC470387
0.8298	Intermediate Similarity	NPC47853
0.8283	Intermediate Similarity	NPC202793
0.8283	Intermediate Similarity	NPC474558
0.8283	Intermediate Similarity	NPC84928
0.828	Intermediate Similarity	NPC250753
0.828	Intermediate Similarity	NPC198242
0.828	Intermediate Similarity	NPC211403
0.8265	Intermediate Similarity	NPC309388
0.8265	Intermediate Similarity	NPC475803
0.8247	Intermediate Similarity	NPC293866
0.8247	Intermediate Similarity	NPC287676
0.8247	Intermediate Similarity	NPC293890
0.8247	Intermediate Similarity	NPC267921
0.8229	Intermediate Similarity	NPC10864
0.8229	Intermediate Similarity	NPC469810
0.8218	Intermediate Similarity	NPC63841
0.82	Intermediate Similarity	NPC4115
0.82	Intermediate Similarity	NPC138908
0.82	Intermediate Similarity	NPC200957
0.8182	Intermediate Similarity	NPC87927
0.8182	Intermediate Similarity	NPC216114
0.8182	Intermediate Similarity	NPC96217
0.8163	Intermediate Similarity	NPC471790
0.8163	Intermediate Similarity	NPC148279
0.8163	Intermediate Similarity	NPC14634
0.8144	Intermediate Similarity	NPC16911
0.8144	Intermediate Similarity	NPC472028
0.8144	Intermediate Similarity	NPC477653
0.8144	Intermediate Similarity	NPC78427
0.8144	Intermediate Similarity	NPC26270
0.8137	Intermediate Similarity	NPC469983
0.8125	Intermediate Similarity	NPC29410
0.8125	Intermediate Similarity	NPC200054
0.8125	Intermediate Similarity	NPC13949
0.8125	Intermediate Similarity	NPC219353
0.8119	Intermediate Similarity	NPC176949
0.8119	Intermediate Similarity	NPC186054
0.8119	Intermediate Similarity	NPC166993
0.8119	Intermediate Similarity	NPC201908
0.8119	Intermediate Similarity	NPC61071
0.81	Intermediate Similarity	NPC98603
0.81	Intermediate Similarity	NPC244247
0.8077	Intermediate Similarity	NPC476964
0.8068	Intermediate Similarity	NPC274522
0.8068	Intermediate Similarity	NPC476265
0.8061	Intermediate Similarity	NPC470388
0.8061	Intermediate Similarity	NPC94906
0.8061	Intermediate Similarity	NPC475392
0.8061	Intermediate Similarity	NPC475385
0.8061	Intermediate Similarity	NPC475202
0.8058	Intermediate Similarity	NPC85391
0.8058	Intermediate Similarity	NPC471093
0.8058	Intermediate Similarity	NPC100908
0.8043	Intermediate Similarity	NPC476932
0.8041	Intermediate Similarity	NPC474921
0.8039	Intermediate Similarity	NPC218123
0.8039	Intermediate Similarity	NPC471094
0.8039	Intermediate Similarity	NPC473410
0.8039	Intermediate Similarity	NPC112895
0.8039	Intermediate Similarity	NPC231278
0.8039	Intermediate Similarity	NPC273155
0.8039	Intermediate Similarity	NPC469984
0.8039	Intermediate Similarity	NPC232133
0.8021	Intermediate Similarity	NPC98639
0.802	Intermediate Similarity	NPC12823
0.8	Intermediate Similarity	NPC209298
0.8	Intermediate Similarity	NPC122811
0.8	Intermediate Similarity	NPC277074
0.8	Intermediate Similarity	NPC294263
0.7981	Intermediate Similarity	NPC146945
0.7981	Intermediate Similarity	NPC171888
0.7981	Intermediate Similarity	NPC29505
0.7981	Intermediate Similarity	NPC329953
0.798	Intermediate Similarity	NPC71706
0.7979	Intermediate Similarity	NPC475776
0.7961	Intermediate Similarity	NPC274827
0.7941	Intermediate Similarity	NPC96333
0.7941	Intermediate Similarity	NPC471474
0.7941	Intermediate Similarity	NPC88833
0.7938	Intermediate Similarity	NPC58052
0.7938	Intermediate Similarity	NPC111684
0.7935	Intermediate Similarity	NPC83242
0.7921	Intermediate Similarity	NPC101842
0.7921	Intermediate Similarity	NPC301787
0.7917	Intermediate Similarity	NPC153775
0.7917	Intermediate Similarity	NPC224410
0.7917	Intermediate Similarity	NPC474841
0.7917	Intermediate Similarity	NPC471446
0.7917	Intermediate Similarity	NPC215271
0.7917	Intermediate Similarity	NPC261333
0.7917	Intermediate Similarity	NPC104371
0.7917	Intermediate Similarity	NPC292374
0.7917	Intermediate Similarity	NPC29247
0.7917	Intermediate Similarity	NPC473434
0.7917	Intermediate Similarity	NPC169751
0.7917	Intermediate Similarity	NPC129004
0.7917	Intermediate Similarity	NPC111524
0.7917	Intermediate Similarity	NPC272635
0.7917	Intermediate Similarity	NPC101233
0.7917	Intermediate Similarity	NPC91772
0.7917	Intermediate Similarity	NPC289539
0.7917	Intermediate Similarity	NPC100257
0.79	Intermediate Similarity	NPC124544
0.7885	Intermediate Similarity	NPC137104
0.7885	Intermediate Similarity	NPC474786
0.7885	Intermediate Similarity	NPC320383
0.7879	Intermediate Similarity	NPC180733
0.7879	Intermediate Similarity	NPC41971
0.7879	Intermediate Similarity	NPC477656
0.7879	Intermediate Similarity	NPC37047
0.7864	Intermediate Similarity	NPC469733
0.7864	Intermediate Similarity	NPC55973
0.7864	Intermediate Similarity	NPC469729
0.7857	Intermediate Similarity	NPC473456
0.7857	Intermediate Similarity	NPC253586
0.7849	Intermediate Similarity	NPC259009
0.7849	Intermediate Similarity	NPC30421
0.7849	Intermediate Similarity	NPC175293
0.7843	Intermediate Similarity	NPC164600
0.7843	Intermediate Similarity	NPC37600
0.7843	Intermediate Similarity	NPC103172
0.7843	Intermediate Similarity	NPC307660
0.7843	Intermediate Similarity	NPC222833
0.7843	Intermediate Similarity	NPC56656
0.7843	Intermediate Similarity	NPC295366
0.7843	Intermediate Similarity	NPC130511
0.7835	Intermediate Similarity	NPC210214
0.7835	Intermediate Similarity	NPC274417
0.7835	Intermediate Similarity	NPC288906
0.7835	Intermediate Similarity	NPC41070
0.7835	Intermediate Similarity	NPC56369
0.7835	Intermediate Similarity	NPC263135
0.783	Intermediate Similarity	NPC208998
0.783	Intermediate Similarity	NPC471252
0.783	Intermediate Similarity	NPC7921
0.7826	Intermediate Similarity	NPC477205
0.7822	Intermediate Similarity	NPC95585
0.7822	Intermediate Similarity	NPC478057
0.7822	Intermediate Similarity	NPC282233
0.7822	Intermediate Similarity	NPC95899
0.7812	Intermediate Similarity	NPC181594
0.7812	Intermediate Similarity	NPC199543
0.7812	Intermediate Similarity	NPC144739
0.781	Intermediate Similarity	NPC213320
0.78	Intermediate Similarity	NPC121218
0.78	Intermediate Similarity	NPC111292
0.78	Intermediate Similarity	NPC75941
0.78	Intermediate Similarity	NPC39683
0.78	Intermediate Similarity	NPC252614
0.78	Intermediate Similarity	NPC253886
0.78	Intermediate Similarity	NPC295276
0.7789	Intermediate Similarity	NPC328141
0.7789	Intermediate Similarity	NPC80401
0.7788	Intermediate Similarity	NPC102741
0.7788	Intermediate Similarity	NPC131903
0.7788	Intermediate Similarity	NPC474242
0.7788	Intermediate Similarity	NPC16657
0.7788	Intermediate Similarity	NPC204652
0.7778	Intermediate Similarity	NPC475951
0.7778	Intermediate Similarity	NPC469986
0.7767	Intermediate Similarity	NPC471461
0.7767	Intermediate Similarity	NPC469746
0.7767	Intermediate Similarity	NPC67745

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 NPC476934 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	2679
0.2-0.3	3886
0.3-0.4	1497
0.4-0.5	451
0.5-0.6	197
0.6-0.7	132
0.7-0.8	12
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
0.7849	Intermediate Similarity	NPD3573	Approved
0.7524	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7900	Approved
0.7374	Intermediate Similarity	NPD7748	Approved
0.7333	Intermediate Similarity	NPD6008	Approved
0.7216	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD8034	Phase 2
0.7172	Intermediate Similarity	NPD8035	Phase 2
0.7172	Intermediate Similarity	NPD7515	Phase 2
0.7157	Intermediate Similarity	NPD7902	Approved
0.7105	Intermediate Similarity	NPD6319	Approved
0.7103	Intermediate Similarity	NPD5697	Approved
0.7083	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8328	Phase 3
0.7037	Intermediate Similarity	NPD6899	Approved
0.7037	Intermediate Similarity	NPD6881	Approved
0.701	Intermediate Similarity	NPD7521	Approved
0.701	Intermediate Similarity	NPD6409	Approved
0.701	Intermediate Similarity	NPD6684	Approved
0.701	Intermediate Similarity	NPD7334	Approved
0.701	Intermediate Similarity	NPD5330	Approved
0.701	Intermediate Similarity	NPD7146	Approved
0.7009	Intermediate Similarity	NPD5739	Approved
0.7009	Intermediate Similarity	NPD6402	Approved
0.7009	Intermediate Similarity	NPD6675	Approved
0.7009	Intermediate Similarity	NPD7128	Approved
0.7	Intermediate Similarity	NPD6411	Approved
0.6975	Remote Similarity	NPD7736	Approved
0.6972	Remote Similarity	NPD6014	Approved
0.6972	Remote Similarity	NPD6012	Approved
0.6972	Remote Similarity	NPD6013	Approved
0.6944	Remote Similarity	NPD5701	Approved
0.6923	Remote Similarity	NPD7638	Approved
0.6917	Remote Similarity	NPD7319	Approved
0.6909	Remote Similarity	NPD6883	Approved
0.6909	Remote Similarity	NPD7102	Approved
0.6909	Remote Similarity	NPD7290	Approved
0.6881	Remote Similarity	NPD7320	Approved
0.6881	Remote Similarity	NPD6011	Approved
0.6875	Remote Similarity	NPD4632	Approved
0.6869	Remote Similarity	NPD5737	Approved
0.6869	Remote Similarity	NPD6672	Approved
0.6869	Remote Similarity	NPD6903	Approved
0.6864	Remote Similarity	NPD7492	Approved
0.6857	Remote Similarity	NPD7640	Approved
0.6857	Remote Similarity	NPD7639	Approved
0.6847	Remote Similarity	NPD6847	Approved
0.6847	Remote Similarity	NPD6617	Approved
0.6847	Remote Similarity	NPD6869	Approved
0.6847	Remote Similarity	NPD6649	Approved
0.6847	Remote Similarity	NPD6650	Approved
0.6847	Remote Similarity	NPD8130	Phase 1
0.6842	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6373	Approved
0.6818	Remote Similarity	NPD6372	Approved
0.681	Remote Similarity	NPD6054	Approved
0.6807	Remote Similarity	NPD6616	Approved
0.68	Remote Similarity	NPD6101	Approved
0.68	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6882	Approved
0.6786	Remote Similarity	NPD8297	Approved
0.6771	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4634	Approved
0.6752	Remote Similarity	NPD6015	Approved
0.6752	Remote Similarity	NPD6921	Approved
0.6752	Remote Similarity	NPD6016	Approved
0.675	Remote Similarity	NPD7078	Approved
0.6726	Remote Similarity	NPD8133	Approved
0.6701	Remote Similarity	NPD4788	Approved
0.6698	Remote Similarity	NPD5285	Approved
0.6698	Remote Similarity	NPD5286	Approved
0.6698	Remote Similarity	NPD4696	Approved
0.6696	Remote Similarity	NPD7115	Discovery
0.6696	Remote Similarity	NPD6009	Approved
0.6695	Remote Similarity	NPD6370	Approved
0.6695	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6079	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD6412	Phase 2
0.6635	Remote Similarity	NPD5695	Phase 3
0.6634	Remote Similarity	NPD6673	Approved
0.6634	Remote Similarity	NPD5328	Approved
0.6634	Remote Similarity	NPD6080	Approved
0.6634	Remote Similarity	NPD6904	Approved
0.6612	Remote Similarity	NPD8293	Discontinued
0.661	Remote Similarity	NPD5983	Phase 2
0.6609	Remote Similarity	NPD6274	Approved
0.6607	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5696	Approved
0.6602	Remote Similarity	NPD5778	Approved
0.6602	Remote Similarity	NPD5779	Approved
0.6602	Remote Similarity	NPD6399	Phase 3
0.6593	Remote Similarity	NPD5777	Approved
0.6577	Remote Similarity	NPD6686	Approved
0.6574	Remote Similarity	NPD4633	Approved
0.6574	Remote Similarity	NPD5225	Approved
0.6574	Remote Similarity	NPD5224	Approved
0.6574	Remote Similarity	NPD5226	Approved
0.6574	Remote Similarity	NPD5211	Phase 2
0.6571	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7732	Phase 3
0.6571	Remote Similarity	NPD5222	Approved
0.6571	Remote Similarity	NPD5221	Approved
0.6566	Remote Similarity	NPD1694	Approved
0.6559	Remote Similarity	NPD3703	Phase 2
0.6549	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD4700	Approved
0.6538	Remote Similarity	NPD6001	Approved
0.6535	Remote Similarity	NPD5208	Approved
0.6526	Remote Similarity	NPD6697	Approved
0.6526	Remote Similarity	NPD6115	Approved
0.6526	Remote Similarity	NPD6118	Approved
0.6526	Remote Similarity	NPD6114	Approved
0.6514	Remote Similarity	NPD5174	Approved
0.6514	Remote Similarity	NPD5175	Approved
0.6509	Remote Similarity	NPD5173	Approved
0.6505	Remote Similarity	NPD5693	Phase 1
0.65	Remote Similarity	NPD3618	Phase 1
0.65	Remote Similarity	NPD7604	Phase 2
0.65	Remote Similarity	NPD6098	Approved
0.6481	Remote Similarity	NPD5223	Approved
0.6455	Remote Similarity	NPD5141	Approved
0.6449	Remote Similarity	NPD4225	Approved
0.6441	Remote Similarity	NPD7101	Approved
0.6441	Remote Similarity	NPD7100	Approved
0.6422	Remote Similarity	NPD7632	Discontinued
0.6415	Remote Similarity	NPD4697	Phase 3
0.641	Remote Similarity	NPD6317	Approved
0.6408	Remote Similarity	NPD5692	Phase 3
0.6393	Remote Similarity	NPD6336	Discontinued
0.6383	Remote Similarity	NPD3702	Approved
0.6381	Remote Similarity	NPD5282	Discontinued
0.6356	Remote Similarity	NPD6314	Approved
0.6356	Remote Similarity	NPD6313	Approved
0.6356	Remote Similarity	NPD6335	Approved
0.6346	Remote Similarity	NPD5694	Approved
0.6346	Remote Similarity	NPD6050	Approved
0.6327	Remote Similarity	NPD1780	Approved
0.6327	Remote Similarity	NPD1779	Approved
0.6325	Remote Similarity	NPD6868	Approved
0.6316	Remote Similarity	NPD6117	Approved
0.6311	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4753	Phase 2
0.63	Remote Similarity	NPD3668	Phase 3
0.63	Remote Similarity	NPD3666	Approved
0.63	Remote Similarity	NPD3665	Phase 1
0.63	Remote Similarity	NPD3133	Approved
0.6286	Remote Similarity	NPD4202	Approved
0.6283	Remote Similarity	NPD5128	Approved
0.6283	Remote Similarity	NPD4730	Approved
0.6283	Remote Similarity	NPD4729	Approved
0.6263	Remote Similarity	NPD3667	Approved
0.6262	Remote Similarity	NPD7614	Phase 1
0.625	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD6116	Phase 1
0.625	Remote Similarity	NPD4768	Approved
0.625	Remote Similarity	NPD5207	Approved
0.6224	Remote Similarity	NPD4695	Discontinued
0.6218	Remote Similarity	NPD7328	Approved
0.6218	Remote Similarity	NPD7327	Approved
0.6216	Remote Similarity	NPD4754	Approved
0.6198	Remote Similarity	NPD6909	Approved
0.6198	Remote Similarity	NPD6908	Approved
0.6198	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7637	Suspended
0.6174	Remote Similarity	NPD5251	Approved
0.6174	Remote Similarity	NPD5249	Phase 3
0.6174	Remote Similarity	NPD5247	Approved
0.6174	Remote Similarity	NPD5250	Approved
0.6174	Remote Similarity	NPD5248	Approved
0.6168	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5210	Approved
0.6168	Remote Similarity	NPD4629	Approved
0.6167	Remote Similarity	NPD7516	Approved
0.616	Remote Similarity	NPD6033	Approved
0.6139	Remote Similarity	NPD4786	Approved
0.6122	Remote Similarity	NPD7645	Phase 2
0.6121	Remote Similarity	NPD5217	Approved
0.6121	Remote Similarity	NPD5216	Approved
0.6121	Remote Similarity	NPD5215	Approved
0.6105	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4223	Phase 3
0.61	Remote Similarity	NPD4221	Approved
0.6078	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6053	Discontinued
0.6066	Remote Similarity	NPD8378	Approved
0.6066	Remote Similarity	NPD8296	Approved
0.6066	Remote Similarity	NPD8380	Approved
0.6066	Remote Similarity	NPD8335	Approved
0.6066	Remote Similarity	NPD8379	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