NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	1.898
LogD:	1.959
LogS:	-2.43
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	4.567
Fsp3:	0.667
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:	-4.705
MDCK Permeability:	1.7630241927690804e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.101

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	80.71904754638672%
Volume Distribution (VD):	1.583
Pgp-substrate:	15.7365140914917%

ADMET: Metabolism

CYP1A2-inhibitor:	0.621
CYP1A2-substrate:	0.588
CYP2C19-inhibitor:	0.222
CYP2C19-substrate:	0.699
CYP2C9-inhibitor:	0.347
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.585
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	7.683
Half-life (T1/2):	0.529

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.789
Drug-inuced Liver Injury (DILI):	0.524
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.693
Maximum Recommended Daily Dose:	0.18
Skin Sensitization:	0.283
Carcinogencity:	0.067
Eye Corrosion:	0.577
Eye Irritation:	0.769
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC37607

Natural Product ID:	NPC37607
*Common Name:**	4-Epi-Isoinuviscolide
IUPAC Name:	(3aS,5aR,8S,8aR,9aR)-8-hydroxy-5,8-dimethyl-1-methylidene-5a,6,7,8a,9,9a-hexahydro-3aH-azuleno[6,5-b]furan-2-one
Synonyms:	4-Epi-Isoinuviscolide
Standard InCHIKey:	APMKESKZWHNIDJ-PFFFPCNUSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-6-13-11(9(2)14(16)18-13)7-12-10(8)4-5-15(12,3)17/h6,10-13,17H,2,4-5,7H2,1,3H3/t10-,11+,12+,13-,15-/m0/s1
SMILES:	CC1=C[C@@H]2OC(=O)C(=C)[C@H]2C[C@@H]2[C@H]1CC[C@]2(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644107
PubChem CID:	53320574
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO33493	inula lineariifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20515062]
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	whole plant	Changshou County, Chongqing, China	2008-Aug	PMID[21109433]
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[21894898]
NPO4280	Inula hupehensis	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21894898]
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	aerial parts	Tibet, China	n.a.	PMID[21924800]
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23499	Carpesium faberi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4280	Inula hupehensis	Species	Asteraceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	28700.0	nM	PMID[528144]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16.3	ug.mL-1	PMID[528145]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	5940.0	nM	PMID[528146]

☑ 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 NPC37607 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	207
0.1-0.2	1250
0.2-0.3	5365
0.3-0.4	13832
0.4-0.5	11000
0.5-0.6	6941
0.6-0.7	3161
0.7-0.8	831
0.8-0.85	84
0.85-0.9	14
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC301969
0.9545	High Similarity	NPC67584
0.9545	High Similarity	NPC52044
0.9524	High Similarity	NPC67493
0.9438	High Similarity	NPC213078
0.9333	High Similarity	NPC161493
0.9302	High Similarity	NPC91248
0.9231	High Similarity	NPC221615
0.9213	High Similarity	NPC127019
0.9176	High Similarity	NPC284534
0.9176	High Similarity	NPC204105
0.9176	High Similarity	NPC300082
0.9111	High Similarity	NPC213698
0.9111	High Similarity	NPC170120
0.9059	High Similarity	NPC156485
0.9	High Similarity	NPC470013
0.9	High Similarity	NPC470010
0.9	High Similarity	NPC323008
0.9	High Similarity	NPC262133
0.8953	High Similarity	NPC235792
0.8864	High Similarity	NPC224652
0.8864	High Similarity	NPC79549
0.883	High Similarity	NPC150923
0.8791	High Similarity	NPC198853
0.8791	High Similarity	NPC477131
0.8778	High Similarity	NPC131209
0.8778	High Similarity	NPC133698
0.8764	High Similarity	NPC215556
0.8721	High Similarity	NPC245665
0.869	High Similarity	NPC182550
0.8667	High Similarity	NPC216284
0.8646	High Similarity	NPC124881
0.8636	High Similarity	NPC56593
0.8588	High Similarity	NPC156658
0.8588	High Similarity	NPC258965
0.8571	High Similarity	NPC155215
0.8556	High Similarity	NPC4986
0.8526	High Similarity	NPC70865
0.8506	High Similarity	NPC250315
0.8478	Intermediate Similarity	NPC135776
0.8478	Intermediate Similarity	NPC258216
0.8471	Intermediate Similarity	NPC470239
0.8471	Intermediate Similarity	NPC470244
0.8444	Intermediate Similarity	NPC178875
0.8427	Intermediate Similarity	NPC64153
0.8409	Intermediate Similarity	NPC194859
0.8409	Intermediate Similarity	NPC224386
0.8404	Intermediate Similarity	NPC18019
0.8404	Intermediate Similarity	NPC24956
0.8372	Intermediate Similarity	NPC276356
0.837	Intermediate Similarity	NPC475925
0.8352	Intermediate Similarity	NPC155935
0.8333	Intermediate Similarity	NPC270270
0.8333	Intermediate Similarity	NPC160138
0.8333	Intermediate Similarity	NPC118601
0.8316	Intermediate Similarity	NPC213947
0.8316	Intermediate Similarity	NPC170143
0.8316	Intermediate Similarity	NPC108475
0.8298	Intermediate Similarity	NPC472873
0.8298	Intermediate Similarity	NPC224689
0.8298	Intermediate Similarity	NPC304886
0.8298	Intermediate Similarity	NPC163228
0.8261	Intermediate Similarity	NPC297474
0.8261	Intermediate Similarity	NPC54065
0.8261	Intermediate Similarity	NPC35809
0.8242	Intermediate Similarity	NPC217983
0.8242	Intermediate Similarity	NPC207114
0.8235	Intermediate Similarity	NPC65603
0.8235	Intermediate Similarity	NPC53581
0.8235	Intermediate Similarity	NPC103987
0.8222	Intermediate Similarity	NPC187661
0.8202	Intermediate Similarity	NPC472957
0.8202	Intermediate Similarity	NPC472958
0.8182	Intermediate Similarity	NPC89555
0.8182	Intermediate Similarity	NPC246076
0.8172	Intermediate Similarity	NPC293001
0.8172	Intermediate Similarity	NPC63193
0.8172	Intermediate Similarity	NPC184063
0.8172	Intermediate Similarity	NPC57304
0.8172	Intermediate Similarity	NPC133888
0.8172	Intermediate Similarity	NPC171360
0.8172	Intermediate Similarity	NPC35959
0.8172	Intermediate Similarity	NPC29821
0.8163	Intermediate Similarity	NPC86077
0.8161	Intermediate Similarity	NPC302426
0.8152	Intermediate Similarity	NPC295312
0.8152	Intermediate Similarity	NPC268298
0.8152	Intermediate Similarity	NPC472872
0.8152	Intermediate Similarity	NPC32922
0.8125	Intermediate Similarity	NPC477949
0.8111	Intermediate Similarity	NPC146850
0.8111	Intermediate Similarity	NPC287015
0.8111	Intermediate Similarity	NPC165162
0.8111	Intermediate Similarity	NPC245434
0.8111	Intermediate Similarity	NPC215364
0.8105	Intermediate Similarity	NPC469873
0.8105	Intermediate Similarity	NPC476053
0.8105	Intermediate Similarity	NPC37408
0.81	Intermediate Similarity	NPC243998
0.81	Intermediate Similarity	NPC223450
0.81	Intermediate Similarity	NPC54737
0.809	Intermediate Similarity	NPC111409
0.809	Intermediate Similarity	NPC318468
0.8085	Intermediate Similarity	NPC153590
0.8085	Intermediate Similarity	NPC60386
0.8085	Intermediate Similarity	NPC473263
0.8085	Intermediate Similarity	NPC81419
0.8085	Intermediate Similarity	NPC473234
0.8085	Intermediate Similarity	NPC473273
0.8085	Intermediate Similarity	NPC200237
0.8085	Intermediate Similarity	NPC179746
0.8085	Intermediate Similarity	NPC308656
0.8068	Intermediate Similarity	NPC126248
0.8065	Intermediate Similarity	NPC129419
0.8065	Intermediate Similarity	NPC19087
0.8065	Intermediate Similarity	NPC51004
0.8061	Intermediate Similarity	NPC171759
0.8043	Intermediate Similarity	NPC202672
0.8041	Intermediate Similarity	NPC45125
0.8023	Intermediate Similarity	NPC470240
0.8023	Intermediate Similarity	NPC476794
0.8022	Intermediate Similarity	NPC107787
0.8022	Intermediate Similarity	NPC284902
0.802	Intermediate Similarity	NPC26617
0.8	Intermediate Similarity	NPC100487
0.8	Intermediate Similarity	NPC474338
0.8	Intermediate Similarity	NPC53011
0.8	Intermediate Similarity	NPC37005
0.8	Intermediate Similarity	NPC226669
0.8	Intermediate Similarity	NPC90453
0.8	Intermediate Similarity	NPC193351
0.8	Intermediate Similarity	NPC138408
0.8	Intermediate Similarity	NPC16887
0.8	Intermediate Similarity	NPC154893
0.7979	Intermediate Similarity	NPC290651
0.7979	Intermediate Similarity	NPC12172
0.7979	Intermediate Similarity	NPC208886
0.7979	Intermediate Similarity	NPC221282
0.7979	Intermediate Similarity	NPC30515
0.7959	Intermediate Similarity	NPC186861
0.7959	Intermediate Similarity	NPC471381
0.7959	Intermediate Similarity	NPC280963
0.7957	Intermediate Similarity	NPC212664
0.7957	Intermediate Similarity	NPC307411
0.7957	Intermediate Similarity	NPC38392
0.7957	Intermediate Similarity	NPC473564
0.7955	Intermediate Similarity	NPC69271
0.7955	Intermediate Similarity	NPC74673
0.7938	Intermediate Similarity	NPC311904
0.7938	Intermediate Similarity	NPC181151
0.7938	Intermediate Similarity	NPC471150
0.7935	Intermediate Similarity	NPC45957
0.7935	Intermediate Similarity	NPC475703
0.7935	Intermediate Similarity	NPC24728
0.7935	Intermediate Similarity	NPC237540
0.7935	Intermediate Similarity	NPC471657
0.7935	Intermediate Similarity	NPC201658
0.7931	Intermediate Similarity	NPC267231
0.7921	Intermediate Similarity	NPC166115
0.7912	Intermediate Similarity	NPC78089
0.7907	Intermediate Similarity	NPC235906
0.79	Intermediate Similarity	NPC474775
0.7895	Intermediate Similarity	NPC475912
0.7895	Intermediate Similarity	NPC475838
0.7895	Intermediate Similarity	NPC125674
0.7895	Intermediate Similarity	NPC228451
0.7895	Intermediate Similarity	NPC476300
0.7889	Intermediate Similarity	NPC128246
0.7889	Intermediate Similarity	NPC272814
0.7882	Intermediate Similarity	NPC472966
0.7882	Intermediate Similarity	NPC143979
0.7882	Intermediate Similarity	NPC320537
0.7879	Intermediate Similarity	NPC475099
0.7872	Intermediate Similarity	NPC71533
0.7872	Intermediate Similarity	NPC179394
0.7872	Intermediate Similarity	NPC474761
0.7872	Intermediate Similarity	NPC475855
0.7872	Intermediate Similarity	NPC476004
0.7872	Intermediate Similarity	NPC106510
0.7872	Intermediate Similarity	NPC144133
0.7872	Intermediate Similarity	NPC62815
0.7865	Intermediate Similarity	NPC25684
0.7865	Intermediate Similarity	NPC325031
0.7865	Intermediate Similarity	NPC35089
0.7865	Intermediate Similarity	NPC10276
0.7865	Intermediate Similarity	NPC281949
0.7865	Intermediate Similarity	NPC301477
0.7864	Intermediate Similarity	NPC59489
0.7864	Intermediate Similarity	NPC139838
0.785	Intermediate Similarity	NPC36754
0.7849	Intermediate Similarity	NPC471149
0.7841	Intermediate Similarity	NPC89128
0.7835	Intermediate Similarity	NPC91771
0.7835	Intermediate Similarity	NPC142529
0.7826	Intermediate Similarity	NPC50637
0.7826	Intermediate Similarity	NPC236692
0.7826	Intermediate Similarity	NPC304558
0.7826	Intermediate Similarity	NPC470242
0.7826	Intermediate Similarity	NPC309757
0.7816	Intermediate Similarity	NPC15975

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 NPC37607 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1859
0.2-0.3	3915
0.3-0.4	2235
0.4-0.5	563
0.5-0.6	299
0.6-0.7	65
0.7-0.8	18
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
0.8556	High Similarity	NPD1695	Approved
0.802	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5362	Discontinued
0.7619	Intermediate Similarity	NPD6371	Approved
0.7527	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5785	Approved
0.7477	Intermediate Similarity	NPD6053	Discontinued
0.7447	Intermediate Similarity	NPD4249	Approved
0.7374	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4250	Approved
0.7368	Intermediate Similarity	NPD4251	Approved
0.734	Intermediate Similarity	NPD5363	Approved
0.7283	Intermediate Similarity	NPD5369	Approved
0.7204	Intermediate Similarity	NPD4270	Approved
0.7204	Intermediate Similarity	NPD4269	Approved
0.7128	Intermediate Similarity	NPD5331	Approved
0.7128	Intermediate Similarity	NPD5332	Approved
0.7097	Intermediate Similarity	NPD4790	Discontinued
0.7083	Intermediate Similarity	NPD5786	Approved
0.699	Remote Similarity	NPD7638	Approved
0.6989	Remote Similarity	NPD4821	Approved
0.6989	Remote Similarity	NPD4252	Approved
0.6989	Remote Similarity	NPD4819	Approved
0.6989	Remote Similarity	NPD4820	Approved
0.6989	Remote Similarity	NPD4822	Approved
0.6989	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD1694	Approved
0.697	Remote Similarity	NPD6698	Approved
0.697	Remote Similarity	NPD46	Approved
0.6947	Remote Similarity	NPD7154	Phase 3
0.6923	Remote Similarity	NPD7640	Approved
0.6923	Remote Similarity	NPD7639	Approved
0.6916	Remote Similarity	NPD6008	Approved
0.6842	Remote Similarity	NPD6435	Approved
0.6774	Remote Similarity	NPD4271	Approved
0.6774	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4268	Approved
0.6765	Remote Similarity	NPD5282	Discontinued
0.6699	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5696	Approved
0.6634	Remote Similarity	NPD7838	Discovery
0.6634	Remote Similarity	NPD5207	Approved
0.6632	Remote Similarity	NPD5368	Approved
0.66	Remote Similarity	NPD6903	Approved
0.6571	Remote Similarity	NPD6083	Phase 2
0.6571	Remote Similarity	NPD6084	Phase 2
0.6569	Remote Similarity	NPD5693	Phase 1
0.6566	Remote Similarity	NPD6409	Approved
0.6566	Remote Similarity	NPD7146	Approved
0.6566	Remote Similarity	NPD6684	Approved
0.6566	Remote Similarity	NPD5330	Approved
0.6566	Remote Similarity	NPD7521	Approved
0.6566	Remote Similarity	NPD7334	Approved
0.6538	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4225	Approved
0.6505	Remote Similarity	NPD5779	Approved
0.6505	Remote Similarity	NPD5778	Approved
0.6486	Remote Similarity	NPD6686	Approved
0.6466	Remote Similarity	NPD7115	Discovery
0.646	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7507	Approved
0.6442	Remote Similarity	NPD6001	Approved
0.6436	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7637	Suspended
0.6408	Remote Similarity	NPD7983	Approved
0.6408	Remote Similarity	NPD5284	Approved
0.6408	Remote Similarity	NPD5281	Approved
0.6396	Remote Similarity	NPD5697	Approved
0.6373	Remote Similarity	NPD6051	Approved
0.6364	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3666	Approved
0.6348	Remote Similarity	NPD4632	Approved
0.6339	Remote Similarity	NPD6011	Approved
0.6339	Remote Similarity	NPD6881	Approved
0.6339	Remote Similarity	NPD6899	Approved
0.6339	Remote Similarity	NPD7320	Approved
0.633	Remote Similarity	NPD7632	Discontinued
0.6327	Remote Similarity	NPD4221	Approved
0.6327	Remote Similarity	NPD4223	Phase 3
0.6327	Remote Similarity	NPD5209	Approved
0.6316	Remote Similarity	NPD6649	Approved
0.6316	Remote Similarity	NPD6650	Approved
0.6306	Remote Similarity	NPD5739	Approved
0.6306	Remote Similarity	NPD6402	Approved
0.6306	Remote Similarity	NPD6675	Approved
0.6306	Remote Similarity	NPD7128	Approved
0.629	Remote Similarity	NPD7319	Approved
0.6283	Remote Similarity	NPD6014	Approved
0.6283	Remote Similarity	NPD6372	Approved
0.6283	Remote Similarity	NPD6013	Approved
0.6283	Remote Similarity	NPD6373	Approved
0.6283	Remote Similarity	NPD6012	Approved
0.6275	Remote Similarity	NPD5208	Approved
0.625	Remote Similarity	NPD5701	Approved
0.6239	Remote Similarity	NPD5344	Discontinued
0.6238	Remote Similarity	NPD5690	Phase 2
0.6238	Remote Similarity	NPD6098	Approved
0.623	Remote Similarity	NPD7492	Approved
0.6228	Remote Similarity	NPD7102	Approved
0.6228	Remote Similarity	NPD7290	Approved
0.6228	Remote Similarity	NPD6883	Approved
0.6226	Remote Similarity	NPD4629	Approved
0.6226	Remote Similarity	NPD5210	Approved
0.6214	Remote Similarity	NPD6080	Approved
0.6214	Remote Similarity	NPD6673	Approved
0.6214	Remote Similarity	NPD4753	Phase 2
0.6214	Remote Similarity	NPD6904	Approved
0.62	Remote Similarity	NPD4786	Approved
0.62	Remote Similarity	NPD4197	Approved
0.619	Remote Similarity	NPD4202	Approved
0.6186	Remote Similarity	NPD6009	Approved
0.6179	Remote Similarity	NPD6616	Approved
0.6174	Remote Similarity	NPD8130	Phase 1
0.6174	Remote Similarity	NPD6617	Approved
0.6174	Remote Similarity	NPD6869	Approved
0.6174	Remote Similarity	NPD6847	Approved
0.6167	Remote Similarity	NPD6054	Approved
0.6167	Remote Similarity	NPD6319	Approved
0.6162	Remote Similarity	NPD3667	Approved
0.6154	Remote Similarity	NPD5692	Phase 3
0.6147	Remote Similarity	NPD6648	Approved
0.6139	Remote Similarity	NPD5329	Approved
0.6134	Remote Similarity	NPD7327	Approved
0.6134	Remote Similarity	NPD7328	Approved
0.6129	Remote Similarity	NPD7078	Approved
0.6121	Remote Similarity	NPD6882	Approved
0.6121	Remote Similarity	NPD8297	Approved
0.6117	Remote Similarity	NPD4518	Approved
0.6117	Remote Similarity	NPD6672	Approved
0.6117	Remote Similarity	NPD5737	Approved
0.6116	Remote Similarity	NPD8033	Approved
0.6116	Remote Similarity	NPD6015	Approved
0.6116	Remote Similarity	NPD5983	Phase 2
0.6116	Remote Similarity	NPD6016	Approved
0.6116	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6412	Phase 2
0.6105	Remote Similarity	NPD8039	Approved
0.61	Remote Similarity	NPD4788	Approved
0.61	Remote Similarity	NPD6695	Phase 3
0.6095	Remote Similarity	NPD6050	Approved
0.6095	Remote Similarity	NPD5694	Approved
0.6087	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7516	Approved
0.608	Remote Similarity	NPD7736	Approved
0.6078	Remote Similarity	NPD5279	Phase 3
0.6078	Remote Similarity	NPD5280	Approved
0.6078	Remote Similarity	NPD4690	Approved
0.6078	Remote Similarity	NPD4138	Approved
0.6078	Remote Similarity	NPD5205	Approved
0.6078	Remote Similarity	NPD4688	Approved
0.6078	Remote Similarity	NPD3618	Phase 1
0.6078	Remote Similarity	NPD4689	Approved
0.6078	Remote Similarity	NPD4693	Phase 3
0.6078	Remote Similarity	NPD4694	Approved
0.6066	Remote Similarity	NPD5988	Approved
0.6066	Remote Similarity	NPD6370	Approved
0.6058	Remote Similarity	NPD5370	Suspended
0.6058	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6101	Approved
0.604	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5211	Phase 2
0.6034	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD8377	Approved
0.6033	Remote Similarity	NPD6059	Approved
0.6033	Remote Similarity	NPD8294	Approved
0.6019	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7839	Suspended
0.6016	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD4696	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD5285	Approved
0.5984	Remote Similarity	NPD8296	Approved
0.5984	Remote Similarity	NPD8379	Approved
0.5984	Remote Similarity	NPD8378	Approved
0.5984	Remote Similarity	NPD8517	Approved
0.5984	Remote Similarity	NPD8516	Approved
0.5984	Remote Similarity	NPD7503	Approved
0.5984	Remote Similarity	NPD8515	Approved
0.5984	Remote Similarity	NPD8335	Approved
0.5984	Remote Similarity	NPD8380	Approved
0.5984	Remote Similarity	NPD8513	Phase 3
0.5982	Remote Similarity	NPD6052	Approved
0.5977	Remote Similarity	NPD3198	Approved
0.5966	Remote Similarity	NPD6274	Approved
0.5963	Remote Similarity	NPD4755	Approved
0.596	Remote Similarity	NPD6930	Phase 2
0.596	Remote Similarity	NPD6931	Approved
0.5948	Remote Similarity	NPD6420	Discontinued
0.5946	Remote Similarity	NPD5223	Approved
0.5943	Remote Similarity	NPD6411	Approved
0.5943	Remote Similarity	NPD8035	Phase 2
0.5943	Remote Similarity	NPD6079	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