NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	254.868
LogP:	2.673
LogD:	2.596
LogS:	-3.804
# Rotatable Bonds:	0
TPSA:	38.83
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	5.272
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:	-4.696
MDCK Permeability:	2.081635466311127e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.127
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	79.16940307617188%
Volume Distribution (VD):	1.633
Pgp-substrate:	15.594103813171387%

ADMET: Metabolism

CYP1A2-inhibitor:	0.178
CYP1A2-substrate:	0.687
CYP2C19-inhibitor:	0.19
CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.206
CYP2C9-substrate:	0.064
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.198
CYP3A4-inhibitor:	0.671
CYP3A4-substrate:	0.566

ADMET: Excretion

Clearance (CL):	14.391
Half-life (T1/2):	0.306

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.641
Drug-inuced Liver Injury (DILI):	0.904
AMES Toxicity:	0.746
Rat Oral Acute Toxicity:	0.872
Maximum Recommended Daily Dose:	0.406
Skin Sensitization:	0.93
Carcinogencity:	0.879
Eye Corrosion:	0.881
Eye Irritation:	0.962
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC270270

Natural Product ID:	NPC270270
*Common Name:**	AIHKZOVNPAYCEL-KYHCNFOCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AIHKZOVNPAYCEL-KYHCNFOCSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-6-12-10(9(2)13(16)17-12)7-15-11(8)4-5-14(15,3)18-15/h8,10-12H,2,4-7H2,1,3H3/t8-,10+,11-,12-,14+,15-/m0/s1
SMILES:	C[C@H]1C[C@H]2[C@H](C[C@]34[C@H]1CC[C@@]3(C)O4)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1912051
PubChem CID:	14313754
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
NPO22238	Inula falconeri	Species	Asteraceae	Eukaryota	aerial parts	Tibet, China	n.a.	PMID[21924800]
NPO32892	inula peacockiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	Whole Plant	n.a.	n.a.	PMID[26394911]
NPO21305	Carpesium macrocephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4637	Inula anatolica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22238	Inula falconeri	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	6

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	110.0	nM	PMID[558514]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	50003.45	nM	PMID[558515]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[558515]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	>	30000.0	nM	PMID[558515]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	IC50	=	38.0	ug.mL-1	PMID[558516]
NPT1173	Organism	Candida albicans SC5314	Candida albicans SC5314	IC50	=	106.5	ug.mL-1	PMID[558516]

☑ 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 NPC270270 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	284
0.1-0.2	2486
0.2-0.3	8855
0.3-0.4	15919
0.4-0.5	8684
0.5-0.6	4837
0.6-0.7	1275
0.7-0.8	257
0.8-0.85	75
0.85-0.9	20
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9294	High Similarity	NPC472872
0.908	High Similarity	NPC155215
0.9048	High Similarity	NPC284534
0.9048	High Similarity	NPC204105
0.9048	High Similarity	NPC300082
0.8989	High Similarity	NPC476053
0.8977	High Similarity	NPC258216
0.8953	High Similarity	NPC224652
0.8953	High Similarity	NPC178875
0.8953	High Similarity	NPC79549
0.8916	High Similarity	NPC246076
0.8851	High Similarity	NPC215556
0.8851	High Similarity	NPC4986
0.8837	High Similarity	NPC118601
0.8804	High Similarity	NPC471381
0.8804	High Similarity	NPC186861
0.8778	High Similarity	NPC163228
0.875	High Similarity	NPC216284
0.8721	High Similarity	NPC470242
0.8652	High Similarity	NPC286341
0.8652	High Similarity	NPC191339
0.8621	High Similarity	NPC24728
0.8588	High Similarity	NPC245665
0.8556	High Similarity	NPC153590
0.8537	High Similarity	NPC208223
0.8523	High Similarity	NPC471149
0.8506	High Similarity	NPC304558
0.8506	High Similarity	NPC56593
0.8506	High Similarity	NPC64153
0.8495	Intermediate Similarity	NPC45125
0.8488	Intermediate Similarity	NPC194859
0.8488	Intermediate Similarity	NPC224386
0.8452	Intermediate Similarity	NPC73052
0.8452	Intermediate Similarity	NPC293418
0.8452	Intermediate Similarity	NPC156658
0.8452	Intermediate Similarity	NPC290508
0.8452	Intermediate Similarity	NPC258965
0.8427	Intermediate Similarity	NPC155935
0.8427	Intermediate Similarity	NPC283409
0.8395	Intermediate Similarity	NPC143979
0.8395	Intermediate Similarity	NPC320537
0.8391	Intermediate Similarity	NPC235792
0.8387	Intermediate Similarity	NPC471150
0.8372	Intermediate Similarity	NPC272814
0.8372	Intermediate Similarity	NPC54468
0.837	Intermediate Similarity	NPC472873
0.8352	Intermediate Similarity	NPC200237
0.8352	Intermediate Similarity	NPC472874
0.8351	Intermediate Similarity	NPC54737
0.8333	Intermediate Similarity	NPC297474
0.8333	Intermediate Similarity	NPC54065
0.8333	Intermediate Similarity	NPC62815
0.8333	Intermediate Similarity	NPC37607
0.8333	Intermediate Similarity	NPC301969
0.8333	Intermediate Similarity	NPC35809
0.8315	Intermediate Similarity	NPC207114
0.8315	Intermediate Similarity	NPC217983
0.8315	Intermediate Similarity	NPC91248
0.8298	Intermediate Similarity	NPC221615
0.8295	Intermediate Similarity	NPC67493
0.8295	Intermediate Similarity	NPC236692
0.8295	Intermediate Similarity	NPC187661
0.8295	Intermediate Similarity	NPC309757
0.828	Intermediate Similarity	NPC91771
0.828	Intermediate Similarity	NPC142529
0.8276	Intermediate Similarity	NPC470238
0.8276	Intermediate Similarity	NPC138647
0.8242	Intermediate Similarity	NPC184063
0.8242	Intermediate Similarity	NPC133888
0.8242	Intermediate Similarity	NPC171360
0.8242	Intermediate Similarity	NPC29821
0.8242	Intermediate Similarity	NPC293001
0.8242	Intermediate Similarity	NPC63193
0.8242	Intermediate Similarity	NPC57304
0.8242	Intermediate Similarity	NPC35959
0.8172	Intermediate Similarity	NPC52044
0.8172	Intermediate Similarity	NPC67584
0.8161	Intermediate Similarity	NPC474472
0.8161	Intermediate Similarity	NPC111409
0.8161	Intermediate Similarity	NPC257358
0.8152	Intermediate Similarity	NPC60386
0.8152	Intermediate Similarity	NPC308656
0.8152	Intermediate Similarity	NPC473273
0.8152	Intermediate Similarity	NPC135776
0.8152	Intermediate Similarity	NPC473234
0.8152	Intermediate Similarity	NPC473263
0.814	Intermediate Similarity	NPC47635
0.814	Intermediate Similarity	NPC126248
0.8132	Intermediate Similarity	NPC19087
0.81	Intermediate Similarity	NPC139838
0.81	Intermediate Similarity	NPC59489
0.809	Intermediate Similarity	NPC238593
0.8085	Intermediate Similarity	NPC213078
0.8065	Intermediate Similarity	NPC323008
0.8065	Intermediate Similarity	NPC473331
0.8065	Intermediate Similarity	NPC470010
0.8065	Intermediate Similarity	NPC470013
0.8065	Intermediate Similarity	NPC127019
0.8065	Intermediate Similarity	NPC262133
0.8065	Intermediate Similarity	NPC198853
0.8043	Intermediate Similarity	NPC131209
0.8043	Intermediate Similarity	NPC133698
0.8023	Intermediate Similarity	NPC6823
0.8023	Intermediate Similarity	NPC276356
0.8022	Intermediate Similarity	NPC38392
0.8	Intermediate Similarity	NPC5130
0.8	Intermediate Similarity	NPC161493
0.8	Intermediate Similarity	NPC231889
0.8	Intermediate Similarity	NPC475703
0.8	Intermediate Similarity	NPC181151
0.8	Intermediate Similarity	NPC311904
0.8	Intermediate Similarity	NPC190753
0.798	Intermediate Similarity	NPC223450
0.798	Intermediate Similarity	NPC44004
0.798	Intermediate Similarity	NPC243998
0.7979	Intermediate Similarity	NPC170120
0.7979	Intermediate Similarity	NPC213698
0.7955	Intermediate Similarity	NPC128246
0.7938	Intermediate Similarity	NPC171759
0.7935	Intermediate Similarity	NPC312042
0.7907	Intermediate Similarity	NPC182550
0.7901	Intermediate Similarity	NPC5714
0.7895	Intermediate Similarity	NPC24956
0.7895	Intermediate Similarity	NPC18019
0.7872	Intermediate Similarity	NPC477131
0.7865	Intermediate Similarity	NPC156485
0.7849	Intermediate Similarity	NPC221282
0.7849	Intermediate Similarity	NPC475925
0.7826	Intermediate Similarity	NPC12872
0.7826	Intermediate Similarity	NPC32922
0.7826	Intermediate Similarity	NPC166919
0.7826	Intermediate Similarity	NPC151770
0.7826	Intermediate Similarity	NPC168679
0.7816	Intermediate Similarity	NPC74673
0.7816	Intermediate Similarity	NPC474981
0.7816	Intermediate Similarity	NPC69271
0.7812	Intermediate Similarity	NPC108475
0.7812	Intermediate Similarity	NPC213947
0.7812	Intermediate Similarity	NPC170143
0.7812	Intermediate Similarity	NPC474313
0.7802	Intermediate Similarity	NPC201658
0.7802	Intermediate Similarity	NPC186148
0.7789	Intermediate Similarity	NPC224689
0.7789	Intermediate Similarity	NPC167893
0.7778	Intermediate Similarity	NPC38468
0.7778	Intermediate Similarity	NPC319795
0.7778	Intermediate Similarity	NPC149725
0.7778	Intermediate Similarity	NPC50362
0.7778	Intermediate Similarity	NPC304509
0.7778	Intermediate Similarity	NPC47958
0.7753	Intermediate Similarity	NPC39588
0.7745	Intermediate Similarity	NPC115352
0.7742	Intermediate Similarity	NPC329857
0.7742	Intermediate Similarity	NPC475748
0.7742	Intermediate Similarity	NPC469718
0.7727	Intermediate Similarity	NPC10276
0.7727	Intermediate Similarity	NPC35089
0.7717	Intermediate Similarity	NPC58219
0.7717	Intermediate Similarity	NPC177629
0.7701	Intermediate Similarity	NPC80999
0.7701	Intermediate Similarity	NPC617
0.7692	Intermediate Similarity	NPC50637
0.7692	Intermediate Similarity	NPC469676
0.7684	Intermediate Similarity	NPC476267
0.7684	Intermediate Similarity	NPC473330
0.7684	Intermediate Similarity	NPC140543
0.7684	Intermediate Similarity	NPC473316
0.7674	Intermediate Similarity	NPC53581
0.7674	Intermediate Similarity	NPC103987
0.766	Intermediate Similarity	NPC70251
0.766	Intermediate Similarity	NPC290651
0.766	Intermediate Similarity	NPC475881
0.766	Intermediate Similarity	NPC20713
0.7647	Intermediate Similarity	NPC471491
0.7642	Intermediate Similarity	NPC255450
0.7642	Intermediate Similarity	NPC170692
0.7634	Intermediate Similarity	NPC92974
0.7614	Intermediate Similarity	NPC51507
0.7604	Intermediate Similarity	NPC475900
0.7604	Intermediate Similarity	NPC56369
0.7582	Intermediate Similarity	NPC161957
0.7582	Intermediate Similarity	NPC474547
0.7579	Intermediate Similarity	NPC212486
0.7576	Intermediate Similarity	NPC150923
0.7576	Intermediate Similarity	NPC471767
0.7556	Intermediate Similarity	NPC128429
0.7553	Intermediate Similarity	NPC246173
0.7551	Intermediate Similarity	NPC208233
0.7528	Intermediate Similarity	NPC141810
0.7527	Intermediate Similarity	NPC202672
0.7526	Intermediate Similarity	NPC126156
0.7526	Intermediate Similarity	NPC476009
0.75	Intermediate Similarity	NPC66581
0.75	Intermediate Similarity	NPC476015
0.75	Intermediate Similarity	NPC284902
0.75	Intermediate Similarity	NPC474949
0.75	Intermediate Similarity	NPC474035
0.75	Intermediate Similarity	NPC474762
0.75	Intermediate Similarity	NPC162071
0.75	Intermediate Similarity	NPC250594

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 NPC270270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	3099
0.2-0.3	3874
0.3-0.4	1299
0.4-0.5	355
0.5-0.6	164
0.6-0.7	12
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8851	High Similarity	NPD1695	Approved
0.7778	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6008	Approved
0.7212	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6053	Discontinued
0.6852	Remote Similarity	NPD6371	Approved
0.6495	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5362	Discontinued
0.6429	Remote Similarity	NPD4249	Approved
0.6364	Remote Similarity	NPD4250	Approved
0.6364	Remote Similarity	NPD4251	Approved
0.6354	Remote Similarity	NPD6435	Approved
0.6337	Remote Similarity	NPD46	Approved
0.6337	Remote Similarity	NPD5785	Approved
0.6337	Remote Similarity	NPD6698	Approved
0.6327	Remote Similarity	NPD1694	Approved
0.6263	Remote Similarity	NPD5786	Approved
0.625	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5207	Approved
0.6162	Remote Similarity	NPD5363	Approved
0.6154	Remote Similarity	NPD6001	Approved
0.6146	Remote Similarity	NPD5368	Approved
0.6139	Remote Similarity	NPD6903	Approved
0.6117	Remote Similarity	NPD5693	Phase 1
0.61	Remote Similarity	NPD7146	Approved
0.61	Remote Similarity	NPD6409	Approved
0.61	Remote Similarity	NPD7334	Approved
0.61	Remote Similarity	NPD7521	Approved
0.61	Remote Similarity	NPD5330	Approved
0.61	Remote Similarity	NPD6684	Approved
0.6023	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4270	Approved
0.602	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4269	Approved
0.6019	Remote Similarity	NPD7838	Discovery
0.6	Remote Similarity	NPD5282	Discontinued
0.5982	Remote Similarity	NPD5697	Approved
0.598	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4819	Approved
0.5979	Remote Similarity	NPD4821	Approved
0.5979	Remote Similarity	NPD4820	Approved
0.5979	Remote Similarity	NPD4822	Approved
0.5979	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD1700	Approved
0.596	Remote Similarity	NPD5332	Approved
0.596	Remote Similarity	NPD5331	Approved
0.5948	Remote Similarity	NPD4632	Approved
0.5935	Remote Similarity	NPD7507	Approved
0.5929	Remote Similarity	NPD6881	Approved
0.5929	Remote Similarity	NPD7320	Approved
0.5929	Remote Similarity	NPD6011	Approved
0.5929	Remote Similarity	NPD6899	Approved
0.5926	Remote Similarity	NPD7638	Approved
0.5918	Remote Similarity	NPD4790	Discontinued
0.5913	Remote Similarity	NPD6649	Approved
0.5913	Remote Similarity	NPD6650	Approved
0.5905	Remote Similarity	NPD6399	Phase 3
0.5893	Remote Similarity	NPD7128	Approved
0.5893	Remote Similarity	NPD6675	Approved
0.5893	Remote Similarity	NPD5739	Approved
0.5893	Remote Similarity	NPD6402	Approved
0.5877	Remote Similarity	NPD6372	Approved
0.5877	Remote Similarity	NPD6013	Approved
0.5877	Remote Similarity	NPD6012	Approved
0.5877	Remote Similarity	NPD6373	Approved
0.5877	Remote Similarity	NPD6014	Approved
0.5872	Remote Similarity	NPD7639	Approved
0.5872	Remote Similarity	NPD7640	Approved
0.5859	Remote Similarity	NPD5209	Approved
0.5854	Remote Similarity	NPD7492	Approved
0.5841	Remote Similarity	NPD5701	Approved
0.5841	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD7102	Approved
0.5826	Remote Similarity	NPD6883	Approved
0.5826	Remote Similarity	NPD7290	Approved
0.5825	Remote Similarity	NPD5208	Approved
0.5816	Remote Similarity	NPD4252	Approved
0.581	Remote Similarity	NPD7983	Approved
0.581	Remote Similarity	NPD8034	Phase 2
0.581	Remote Similarity	NPD8035	Phase 2
0.5806	Remote Similarity	NPD6616	Approved
0.58	Remote Similarity	NPD4788	Approved
0.58	Remote Similarity	NPD7154	Phase 3
0.5798	Remote Similarity	NPD6009	Approved
0.5798	Remote Similarity	NPD7115	Discovery
0.5794	Remote Similarity	NPD7319	Approved
0.5794	Remote Similarity	NPD5695	Phase 3
0.5785	Remote Similarity	NPD6054	Approved
0.5785	Remote Similarity	NPD6319	Approved
0.5784	Remote Similarity	NPD6098	Approved
0.578	Remote Similarity	NPD5696	Approved
0.5776	Remote Similarity	NPD6869	Approved
0.5776	Remote Similarity	NPD6847	Approved
0.5776	Remote Similarity	NPD6617	Approved
0.5776	Remote Similarity	NPD8130	Phase 1
0.5773	Remote Similarity	NPD4268	Approved
0.5773	Remote Similarity	NPD4271	Approved
0.5772	Remote Similarity	NPD7604	Phase 2
0.5769	Remote Similarity	NPD6904	Approved
0.5769	Remote Similarity	NPD6080	Approved
0.5769	Remote Similarity	NPD6051	Approved
0.5769	Remote Similarity	NPD6673	Approved
0.576	Remote Similarity	NPD7078	Approved
0.5755	Remote Similarity	NPD5778	Approved
0.5755	Remote Similarity	NPD5779	Approved
0.5738	Remote Similarity	NPD5983	Phase 2
0.5738	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6015	Approved
0.5738	Remote Similarity	NPD6016	Approved
0.5727	Remote Similarity	NPD6648	Approved
0.5726	Remote Similarity	NPD8297	Approved
0.5726	Remote Similarity	NPD6882	Approved
0.5714	Remote Similarity	NPD5692	Phase 3
0.5714	Remote Similarity	NPD7736	Approved
0.5691	Remote Similarity	NPD6370	Approved
0.5691	Remote Similarity	NPD5988	Approved
0.569	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD6084	Phase 2
0.5688	Remote Similarity	NPD6083	Phase 2
0.5678	Remote Similarity	NPD8133	Approved
0.5676	Remote Similarity	NPD5344	Discontinued
0.5673	Remote Similarity	NPD6672	Approved
0.5673	Remote Similarity	NPD5737	Approved
0.566	Remote Similarity	NPD5694	Approved
0.566	Remote Similarity	NPD6050	Approved
0.566	Remote Similarity	NPD5281	Approved
0.566	Remote Similarity	NPD5284	Approved
0.5656	Remote Similarity	NPD6059	Approved
0.5652	Remote Similarity	NPD6686	Approved
0.5641	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD8293	Discontinued
0.5632	Remote Similarity	NPD3198	Approved
0.5625	Remote Similarity	NPD3702	Approved
0.5625	Remote Similarity	NPD5211	Phase 2
0.5612	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD4238	Approved
0.5612	Remote Similarity	NPD4802	Phase 2
0.5603	Remote Similarity	NPD4061	Clinical (unspecified phase)

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