NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.11
Volume:	255.515
LogP:	3.194
LogD:	3.115
LogS:	-4.373
# Rotatable Bonds:	0
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.762
Synthetic Accessibility Score:	4.241
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.757
MDCK Permeability:	2.4289038265123963e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	97.8740005493164%
Volume Distribution (VD):	1.329
Pgp-substrate:	2.5175886154174805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.851
CYP1A2-substrate:	0.735
CYP2C19-inhibitor:	0.181
CYP2C19-substrate:	0.775
CYP2C9-inhibitor:	0.382
CYP2C9-substrate:	0.543
CYP2D6-inhibitor:	0.088
CYP2D6-substrate:	0.352
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.351

ADMET: Excretion

Clearance (CL):	11.474
Half-life (T1/2):	0.683

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.91
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.21
Rat Oral Acute Toxicity:	0.757
Maximum Recommended Daily Dose:	0.536
Skin Sensitization:	0.66
Carcinogencity:	0.904
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC299235

Natural Product ID:	NPC299235
*Common Name:**	(5Alpha,8Alpha)-2-Oxo-1(10),3,7(11)-Guaiatrien-12,8-Olide
IUPAC Name:	(3aS,8aS)-1,5,8-trimethyl-3a,4,8a,9-tetrahydroazuleno[6,5-b]furan-2,6-dione
Synonyms:
Standard InCHIKey:	CTXCWPVELDJQRF-GWCFXTLKSA-N
Standard InCHI:	InChI=1S/C15H16O3/c1-7-4-12(16)14-8(2)5-13-11(6-10(7)14)9(3)15(17)18-13/h4,10,13H,5-6H2,1-3H3/t10-,13-/m0/s1
SMILES:	CC1=CC(=O)C2=C(C)C[C@H]3C(=C(C)C(=O)O3)C[C@@H]12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501260
PubChem CID:	3013843
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679319]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	8800.0	nM	PMID[453571]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	>	100000.0	nM	PMID[453571]

☑ 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 NPC299235 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	204
0.1-0.2	1394
0.2-0.3	6537
0.3-0.4	16118
0.4-0.5	9937
0.5-0.6	5741
0.6-0.7	2288
0.7-0.8	417
0.8-0.85	46
0.85-0.9	14
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC302426
0.8875	High Similarity	NPC78089
0.8846	High Similarity	NPC10276
0.8846	High Similarity	NPC35089
0.8816	High Similarity	NPC195785
0.8816	High Similarity	NPC65603
0.8816	High Similarity	NPC15975
0.88	High Similarity	NPC193351
0.88	High Similarity	NPC138408
0.88	High Similarity	NPC226669
0.8765	High Similarity	NPC107787
0.875	High Similarity	NPC115786
0.8718	High Similarity	NPC74673
0.8718	High Similarity	NPC69271
0.859	High Similarity	NPC264227
0.859	High Similarity	NPC472965
0.859	High Similarity	NPC182550
0.859	High Similarity	NPC63649
0.85	High Similarity	NPC173609
0.8481	Intermediate Similarity	NPC276356
0.8462	Intermediate Similarity	NPC128276
0.8452	Intermediate Similarity	NPC268298
0.8442	Intermediate Similarity	NPC123360
0.8395	Intermediate Similarity	NPC215294
0.8395	Intermediate Similarity	NPC39588
0.8375	Intermediate Similarity	NPC281949
0.8375	Intermediate Similarity	NPC39411
0.8375	Intermediate Similarity	NPC255580
0.8375	Intermediate Similarity	NPC301477
0.8375	Intermediate Similarity	NPC25684
0.8375	Intermediate Similarity	NPC471325
0.8354	Intermediate Similarity	NPC178277
0.8353	Intermediate Similarity	NPC129419
0.8333	Intermediate Similarity	NPC476794
0.8333	Intermediate Similarity	NPC57744
0.8333	Intermediate Similarity	NPC187568
0.8333	Intermediate Similarity	NPC41780
0.8333	Intermediate Similarity	NPC470240
0.8312	Intermediate Similarity	NPC155587
0.8293	Intermediate Similarity	NPC475100
0.825	Intermediate Similarity	NPC223904
0.8228	Intermediate Similarity	NPC471220
0.8228	Intermediate Similarity	NPC472960
0.8214	Intermediate Similarity	NPC237540
0.8205	Intermediate Similarity	NPC235906
0.8193	Intermediate Similarity	NPC33570
0.8193	Intermediate Similarity	NPC21471
0.8193	Intermediate Similarity	NPC161957
0.8182	Intermediate Similarity	NPC469643
0.8182	Intermediate Similarity	NPC469641
0.8182	Intermediate Similarity	NPC476355
0.8171	Intermediate Similarity	NPC318468
0.8171	Intermediate Similarity	NPC193198
0.8158	Intermediate Similarity	NPC163003
0.8133	Intermediate Similarity	NPC296522
0.8133	Intermediate Similarity	NPC144511
0.8125	Intermediate Similarity	NPC470244
0.8125	Intermediate Similarity	NPC469690
0.8125	Intermediate Similarity	NPC470239
0.8108	Intermediate Similarity	NPC472266
0.8072	Intermediate Similarity	NPC165287
0.8052	Intermediate Similarity	NPC269206
0.8052	Intermediate Similarity	NPC58956
0.8052	Intermediate Similarity	NPC472956
0.8052	Intermediate Similarity	NPC295633
0.8049	Intermediate Similarity	NPC35556
0.8026	Intermediate Similarity	NPC472955
0.8	Intermediate Similarity	NPC218477
0.7976	Intermediate Similarity	NPC165162
0.7975	Intermediate Similarity	NPC472967
0.7975	Intermediate Similarity	NPC473223
0.7975	Intermediate Similarity	NPC266159
0.7952	Intermediate Similarity	NPC475947
0.7949	Intermediate Similarity	NPC294434
0.7949	Intermediate Similarity	NPC117746
0.7949	Intermediate Similarity	NPC140287
0.7949	Intermediate Similarity	NPC15499
0.7949	Intermediate Similarity	NPC259599
0.7927	Intermediate Similarity	NPC42470
0.7927	Intermediate Similarity	NPC325031
0.7922	Intermediate Similarity	NPC84038
0.7922	Intermediate Similarity	NPC129665
0.7901	Intermediate Similarity	NPC469620
0.7901	Intermediate Similarity	NPC471299
0.7901	Intermediate Similarity	NPC270126
0.7882	Intermediate Similarity	NPC284902
0.7882	Intermediate Similarity	NPC261721
0.7875	Intermediate Similarity	NPC53581
0.7875	Intermediate Similarity	NPC103987
0.7875	Intermediate Similarity	NPC122264
0.7857	Intermediate Similarity	NPC30486
0.7857	Intermediate Similarity	NPC156485
0.7857	Intermediate Similarity	NPC82297
0.7838	Intermediate Similarity	NPC131174
0.7831	Intermediate Similarity	NPC89555
0.7821	Intermediate Similarity	NPC474705
0.7791	Intermediate Similarity	NPC475703
0.7778	Intermediate Similarity	NPC93763
0.7778	Intermediate Similarity	NPC108816
0.7765	Intermediate Similarity	NPC215364
0.7765	Intermediate Similarity	NPC235792
0.7763	Intermediate Similarity	NPC470256
0.7763	Intermediate Similarity	NPC276290
0.7753	Intermediate Similarity	NPC135776
0.775	Intermediate Similarity	NPC27205
0.775	Intermediate Similarity	NPC472959
0.7727	Intermediate Similarity	NPC37607
0.7727	Intermediate Similarity	NPC301969
0.7727	Intermediate Similarity	NPC77337
0.7722	Intermediate Similarity	NPC320537
0.7722	Intermediate Similarity	NPC474758
0.7722	Intermediate Similarity	NPC143979
0.7711	Intermediate Similarity	NPC141810
0.7701	Intermediate Similarity	NPC471047
0.7701	Intermediate Similarity	NPC469628
0.7701	Intermediate Similarity	NPC91248
0.7701	Intermediate Similarity	NPC475906
0.7701	Intermediate Similarity	NPC469653
0.7701	Intermediate Similarity	NPC469631
0.7692	Intermediate Similarity	NPC186531
0.7683	Intermediate Similarity	NPC150646
0.7683	Intermediate Similarity	NPC617
0.7674	Intermediate Similarity	NPC474045
0.7674	Intermediate Similarity	NPC67493
0.7674	Intermediate Similarity	NPC64153
0.7674	Intermediate Similarity	NPC261253
0.7667	Intermediate Similarity	NPC477131
0.7667	Intermediate Similarity	NPC167219
0.7662	Intermediate Similarity	NPC265574
0.7654	Intermediate Similarity	NPC180290
0.7654	Intermediate Similarity	NPC171204
0.7654	Intermediate Similarity	NPC208223
0.7654	Intermediate Similarity	NPC116177
0.7654	Intermediate Similarity	NPC476028
0.7654	Intermediate Similarity	NPC320630
0.7654	Intermediate Similarity	NPC7563
0.7654	Intermediate Similarity	NPC141789
0.7654	Intermediate Similarity	NPC97516
0.7647	Intermediate Similarity	NPC238197
0.7647	Intermediate Similarity	NPC96259
0.7647	Intermediate Similarity	NPC141193
0.7647	Intermediate Similarity	NPC149869
0.764	Intermediate Similarity	NPC123177
0.764	Intermediate Similarity	NPC70595
0.764	Intermediate Similarity	NPC300312
0.764	Intermediate Similarity	NPC111114
0.764	Intermediate Similarity	NPC150978
0.764	Intermediate Similarity	NPC74103
0.764	Intermediate Similarity	NPC472953
0.764	Intermediate Similarity	NPC261607
0.764	Intermediate Similarity	NPC284185
0.7625	Intermediate Similarity	NPC244166
0.7625	Intermediate Similarity	NPC329852
0.7619	Intermediate Similarity	NPC85772
0.7619	Intermediate Similarity	NPC474291
0.7614	Intermediate Similarity	NPC212664
0.7614	Intermediate Similarity	NPC4986
0.7614	Intermediate Similarity	NPC32922
0.7614	Intermediate Similarity	NPC295312
0.76	Intermediate Similarity	NPC133904
0.7595	Intermediate Similarity	NPC135703
0.759	Intermediate Similarity	NPC293418
0.759	Intermediate Similarity	NPC290508
0.759	Intermediate Similarity	NPC6823
0.759	Intermediate Similarity	NPC281132
0.759	Intermediate Similarity	NPC73052
0.7586	Intermediate Similarity	NPC160138
0.7586	Intermediate Similarity	NPC72513
0.7586	Intermediate Similarity	NPC478144
0.7586	Intermediate Similarity	NPC312561
0.7564	Intermediate Similarity	NPC469660
0.7564	Intermediate Similarity	NPC67183
0.7561	Intermediate Similarity	NPC474341
0.7561	Intermediate Similarity	NPC196653
0.7561	Intermediate Similarity	NPC471465
0.7561	Intermediate Similarity	NPC267231
0.7561	Intermediate Similarity	NPC253749
0.7561	Intermediate Similarity	NPC184737
0.7558	Intermediate Similarity	NPC245434
0.7558	Intermediate Similarity	NPC189311
0.7529	Intermediate Similarity	NPC474703
0.7529	Intermediate Similarity	NPC53867
0.7528	Intermediate Similarity	NPC253144
0.7528	Intermediate Similarity	NPC62815
0.7528	Intermediate Similarity	NPC71533
0.7528	Intermediate Similarity	NPC106510
0.75	Intermediate Similarity	NPC472966
0.75	Intermediate Similarity	NPC470241
0.75	Intermediate Similarity	NPC226863
0.75	Intermediate Similarity	NPC475902
0.75	Intermediate Similarity	NPC248125
0.75	Intermediate Similarity	NPC224652
0.75	Intermediate Similarity	NPC190718
0.7473	Intermediate Similarity	NPC262133
0.7473	Intermediate Similarity	NPC470010
0.7473	Intermediate Similarity	NPC470013
0.7473	Intermediate Similarity	NPC323008
0.7471	Intermediate Similarity	NPC220478
0.7471	Intermediate Similarity	NPC38576
0.7471	Intermediate Similarity	NPC469483

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 NPC299235 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1920
0.2-0.3	4011
0.3-0.4	2076
0.4-0.5	695
0.5-0.6	202
0.6-0.7	43
0.7-0.8	8
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
0.7614	Intermediate Similarity	NPD1695	Approved
0.7412	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD1694	Approved
0.7326	Intermediate Similarity	NPD5362	Discontinued
0.7326	Intermediate Similarity	NPD7154	Phase 3
0.7209	Intermediate Similarity	NPD5209	Approved
0.7159	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5785	Approved
0.6988	Remote Similarity	NPD8039	Approved
0.6966	Remote Similarity	NPD5363	Approved
0.6957	Remote Similarity	NPD46	Approved
0.6957	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD6903	Approved
0.6889	Remote Similarity	NPD7146	Approved
0.6889	Remote Similarity	NPD6684	Approved
0.6889	Remote Similarity	NPD7521	Approved
0.6889	Remote Similarity	NPD6409	Approved
0.6889	Remote Similarity	NPD5330	Approved
0.6889	Remote Similarity	NPD7334	Approved
0.6832	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4269	Approved
0.6818	Remote Similarity	NPD4270	Approved
0.6778	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5369	Approved
0.6703	Remote Similarity	NPD5786	Approved
0.6635	Remote Similarity	NPD6371	Approved
0.6629	Remote Similarity	NPD6435	Approved
0.6591	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4252	Approved
0.6559	Remote Similarity	NPD5737	Approved
0.6559	Remote Similarity	NPD6672	Approved
0.6556	Remote Similarity	NPD5332	Approved
0.6556	Remote Similarity	NPD5331	Approved
0.6526	Remote Similarity	NPD5693	Phase 1
0.6517	Remote Similarity	NPD4790	Discontinued
0.6404	Remote Similarity	NPD4819	Approved
0.6404	Remote Similarity	NPD4820	Approved
0.6404	Remote Similarity	NPD5368	Approved
0.6404	Remote Similarity	NPD4821	Approved
0.6404	Remote Similarity	NPD4822	Approved
0.6364	Remote Similarity	NPD4271	Approved
0.6364	Remote Similarity	NPD4268	Approved
0.6355	Remote Similarity	NPD6053	Discontinued
0.6344	Remote Similarity	NPD4249	Approved
0.6304	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7638	Approved
0.6289	Remote Similarity	NPD6399	Phase 3
0.6277	Remote Similarity	NPD4250	Approved
0.6277	Remote Similarity	NPD4251	Approved
0.625	Remote Similarity	NPD5207	Approved
0.625	Remote Similarity	NPD7838	Discovery
0.625	Remote Similarity	NPD4756	Discovery
0.6238	Remote Similarity	NPD7640	Approved
0.6238	Remote Similarity	NPD7639	Approved
0.6224	Remote Similarity	NPD5282	Discontinued
0.622	Remote Similarity	NPD7331	Phase 2
0.6211	Remote Similarity	NPD5208	Approved
0.6186	Remote Similarity	NPD7983	Approved
0.6162	Remote Similarity	NPD5695	Phase 3
0.6162	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6904	Approved
0.6146	Remote Similarity	NPD6673	Approved
0.6146	Remote Similarity	NPD6080	Approved
0.6139	Remote Similarity	NPD4225	Approved
0.6132	Remote Similarity	NPD6686	Approved
0.6129	Remote Similarity	NPD3133	Approved
0.6129	Remote Similarity	NPD3666	Approved
0.6129	Remote Similarity	NPD3665	Phase 1
0.6122	Remote Similarity	NPD5778	Approved
0.6122	Remote Similarity	NPD5779	Approved
0.6095	Remote Similarity	NPD6008	Approved
0.6087	Remote Similarity	NPD3667	Approved
0.6082	Remote Similarity	NPD5692	Phase 3
0.6081	Remote Similarity	NPD6927	Phase 3
0.6061	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6001	Approved
0.6061	Remote Similarity	NPD7748	Approved
0.6061	Remote Similarity	NPD7900	Approved
0.604	Remote Similarity	NPD6084	Phase 2
0.604	Remote Similarity	NPD6083	Phase 2
0.6024	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.602	Remote Similarity	NPD5694	Approved
0.602	Remote Similarity	NPD6050	Approved
0.6019	Remote Similarity	NPD2067	Discontinued
0.6	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD6098	Approved
0.6	Remote Similarity	NPD6422	Discontinued
0.5982	Remote Similarity	NPD7115	Discovery
0.598	Remote Similarity	NPD5696	Approved
0.598	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD6051	Approved
0.5979	Remote Similarity	NPD6101	Approved
0.5979	Remote Similarity	NPD5370	Suspended
0.5979	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD3668	Phase 3
0.5957	Remote Similarity	NPD4786	Approved
0.5941	Remote Similarity	NPD7839	Suspended
0.5938	Remote Similarity	NPD3573	Approved
0.5904	Remote Similarity	NPD7341	Phase 2
0.5882	Remote Similarity	NPD7902	Approved
0.5867	Remote Similarity	NPD28	Approved
0.5867	Remote Similarity	NPD29	Approved
0.5859	Remote Similarity	NPD7637	Suspended
0.5859	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD7515	Phase 2
0.5859	Remote Similarity	NPD6411	Approved
0.5833	Remote Similarity	NPD4519	Discontinued
0.5833	Remote Similarity	NPD4623	Approved
0.5833	Remote Similarity	NPD7320	Approved
0.5818	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5328	Approved
0.5814	Remote Similarity	NPD4137	Phase 3
0.5794	Remote Similarity	NPD6675	Approved
0.5794	Remote Similarity	NPD7128	Approved
0.5794	Remote Similarity	NPD5739	Approved
0.5794	Remote Similarity	NPD6402	Approved
0.5783	Remote Similarity	NPD3197	Phase 1
0.5755	Remote Similarity	NPD6647	Phase 2
0.5747	Remote Similarity	NPD4747	Approved
0.5747	Remote Similarity	NPD4691	Approved
0.5745	Remote Similarity	NPD4223	Phase 3
0.5745	Remote Similarity	NPD4221	Approved
0.5741	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5697	Approved
0.5741	Remote Similarity	NPD5701	Approved
0.5729	Remote Similarity	NPD1696	Phase 3
0.5714	Remote Similarity	NPD3172	Approved
0.57	Remote Similarity	NPD5281	Approved
0.57	Remote Similarity	NPD5284	Approved
0.57	Remote Similarity	NPD6079	Approved
0.5699	Remote Similarity	NPD4695	Discontinued
0.5688	Remote Similarity	NPD6881	Approved
0.5688	Remote Similarity	NPD6899	Approved
0.5688	Remote Similarity	NPD6011	Approved
0.5686	Remote Similarity	NPD5654	Approved
0.5682	Remote Similarity	NPD5276	Approved
0.5676	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.566	Remote Similarity	NPD7632	Discontinued
0.5657	Remote Similarity	NPD4753	Phase 2
0.5647	Remote Similarity	NPD3704	Approved
0.5644	Remote Similarity	NPD4202	Approved
0.5641	Remote Similarity	NPD3194	Approved
0.5641	Remote Similarity	NPD3196	Approved
0.5641	Remote Similarity	NPD3195	Phase 2
0.5641	Remote Similarity	NPD4266	Approved
0.5638	Remote Similarity	NPD857	Phase 3
0.5636	Remote Similarity	NPD6372	Approved
0.5636	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6012	Approved
0.5636	Remote Similarity	NPD6013	Approved
0.5636	Remote Similarity	NPD6373	Approved
0.5636	Remote Similarity	NPD6014	Approved
0.5625	Remote Similarity	NPD4197	Approved
0.5619	Remote Similarity	NPD6648	Approved
0.561	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6052	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