NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	264.072
LogP:	1.989
LogD:	1.576
LogS:	-2.535
# Rotatable Bonds:	2
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.555
Synthetic Accessibility Score:	4.759
Fsp3:	0.467
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:	-4.675
MDCK Permeability:	2.3659902581130154e-05
Pgp-inhibitor:	0.631
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.564
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.859

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.176
Plasma Protein Binding (PPB):	82.58454895019531%
Volume Distribution (VD):	0.9
Pgp-substrate:	19.073925018310547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.312
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.098
CYP2C19-substrate:	0.62
CYP2C9-inhibitor:	0.106
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.531
CYP3A4-substrate:	0.312

ADMET: Excretion

Clearance (CL):	14.734
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.875
Drug-inuced Liver Injury (DILI):	0.157
AMES Toxicity:	0.414
Rat Oral Acute Toxicity:	0.941
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.955
Carcinogencity:	0.881
Eye Corrosion:	0.814
Eye Irritation:	0.934
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC264227

Natural Product ID:	NPC264227
*Common Name:**	(3Ar,7S,8As)-7-Methyl-3-Methylidene-6-[(E)-3-Oxobut-1-Enyl]-4,7,8,8A-Tetrahydro-3Ah-Cyclohepta[B]Furan-2-One
IUPAC Name:	(3aR,7S,8aS)-7-methyl-3-methylidene-6-[(E)-3-oxobut-1-enyl]-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
Synonyms:
Standard InCHIKey:	RBRPTFMVULVGIC-ZTIIIDENSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-9-8-14-13(11(3)15(17)18-14)7-6-12(9)5-4-10(2)16/h4-6,9,13-14H,3,7-8H2,1-2H3/b5-4+/t9-,13+,14-/m0/s1
SMILES:	C[C@H]1C[C@H]2[C@H](CC=C1/C=C/C(=O)C)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL404466
PubChem CID:	5281511
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:0000502] Xanthanolides

*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
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26081757]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[27169184]
NPO2494	Xanthium strumarium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2494	Xanthium strumarium	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	470.0	nM	PMID[456426]

☑ 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 NPC264227 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	189
0.1-0.2	1091
0.2-0.3	5628
0.3-0.4	14418
0.4-0.5	11988
0.5-0.6	6241
0.6-0.7	2519
0.7-0.8	535
0.8-0.85	49
0.85-0.9	28
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC63649
1.0	High Similarity	NPC472965
0.9452	High Similarity	NPC193351
0.9452	High Similarity	NPC138408
0.9452	High Similarity	NPC226669
0.9324	High Similarity	NPC472967
0.9324	High Similarity	NPC266159
0.92	High Similarity	NPC65603
0.9091	High Similarity	NPC302426
0.8947	High Similarity	NPC476794
0.8947	High Similarity	NPC470240
0.8933	High Similarity	NPC155587
0.8919	High Similarity	NPC472956
0.8831	High Similarity	NPC472960
0.875	High Similarity	NPC39588
0.8734	High Similarity	NPC35089
0.8734	High Similarity	NPC10276
0.8734	High Similarity	NPC301477
0.8734	High Similarity	NPC281949
0.8734	High Similarity	NPC25684
0.8718	High Similarity	NPC470239
0.8718	High Similarity	NPC182550
0.8718	High Similarity	NPC470244
0.8701	High Similarity	NPC187568
0.8701	High Similarity	NPC41780
0.8642	High Similarity	NPC115786
0.8608	High Similarity	NPC69271
0.8608	High Similarity	NPC74673
0.859	High Similarity	NPC299235
0.8571	High Similarity	NPC235906
0.8553	High Similarity	NPC476355
0.8537	High Similarity	NPC33570
0.8537	High Similarity	NPC161957
0.8537	High Similarity	NPC21471
0.8533	High Similarity	NPC163003
0.8519	High Similarity	NPC318468
0.8514	High Similarity	NPC296522
0.8514	High Similarity	NPC144511
0.85	High Similarity	NPC42470
0.8462	Intermediate Similarity	NPC15975
0.8462	Intermediate Similarity	NPC195785
0.8434	Intermediate Similarity	NPC107787
0.8421	Intermediate Similarity	NPC295633
0.8421	Intermediate Similarity	NPC58956
0.8421	Intermediate Similarity	NPC269206
0.84	Intermediate Similarity	NPC472955
0.8395	Intermediate Similarity	NPC173609
0.8375	Intermediate Similarity	NPC223904
0.8375	Intermediate Similarity	NPC276356
0.8354	Intermediate Similarity	NPC128276
0.8333	Intermediate Similarity	NPC123360
0.8333	Intermediate Similarity	NPC472959
0.8313	Intermediate Similarity	NPC78089
0.8313	Intermediate Similarity	NPC165162
0.8312	Intermediate Similarity	NPC140287
0.8293	Intermediate Similarity	NPC215294
0.8272	Intermediate Similarity	NPC471325
0.825	Intermediate Similarity	NPC178277
0.825	Intermediate Similarity	NPC270126
0.825	Intermediate Similarity	NPC617
0.8228	Intermediate Similarity	NPC57744
0.814	Intermediate Similarity	NPC268298
0.8133	Intermediate Similarity	NPC470256
0.8125	Intermediate Similarity	NPC267231
0.8125	Intermediate Similarity	NPC108816
0.8125	Intermediate Similarity	NPC93763
0.8077	Intermediate Similarity	NPC469643
0.8077	Intermediate Similarity	NPC469641
0.8052	Intermediate Similarity	NPC129665
0.8052	Intermediate Similarity	NPC288667
0.8049	Intermediate Similarity	NPC255580
0.8049	Intermediate Similarity	NPC141810
0.8049	Intermediate Similarity	NPC39411
0.8046	Intermediate Similarity	NPC62815
0.8046	Intermediate Similarity	NPC129419
0.8026	Intermediate Similarity	NPC199557
0.8023	Intermediate Similarity	NPC215831
0.8	Intermediate Similarity	NPC180290
0.8	Intermediate Similarity	NPC97516
0.8	Intermediate Similarity	NPC116177
0.8	Intermediate Similarity	NPC320630
0.8	Intermediate Similarity	NPC171204
0.8	Intermediate Similarity	NPC476028
0.8	Intermediate Similarity	NPC141789
0.8	Intermediate Similarity	NPC7563
0.7976	Intermediate Similarity	NPC141193
0.7976	Intermediate Similarity	NPC96259
0.7976	Intermediate Similarity	NPC156485
0.7955	Intermediate Similarity	NPC70595
0.7955	Intermediate Similarity	NPC123177
0.7955	Intermediate Similarity	NPC150978
0.7955	Intermediate Similarity	NPC74103
0.7952	Intermediate Similarity	NPC89555
0.7952	Intermediate Similarity	NPC178676
0.7945	Intermediate Similarity	NPC474658
0.7931	Intermediate Similarity	NPC73995
0.7927	Intermediate Similarity	NPC281132
0.7901	Intermediate Similarity	NPC471465
0.7901	Intermediate Similarity	NPC196653
0.7895	Intermediate Similarity	NPC218477
0.7882	Intermediate Similarity	NPC215364
0.7882	Intermediate Similarity	NPC235792
0.7882	Intermediate Similarity	NPC177932
0.7882	Intermediate Similarity	NPC110405
0.7857	Intermediate Similarity	NPC272814
0.7857	Intermediate Similarity	NPC475947
0.7857	Intermediate Similarity	NPC250315
0.7848	Intermediate Similarity	NPC320537
0.7848	Intermediate Similarity	NPC117746
0.7848	Intermediate Similarity	NPC294434
0.7848	Intermediate Similarity	NPC472966
0.7848	Intermediate Similarity	NPC143979
0.7848	Intermediate Similarity	NPC259599
0.7848	Intermediate Similarity	NPC15499
0.7841	Intermediate Similarity	NPC253144
0.7841	Intermediate Similarity	NPC469372
0.7831	Intermediate Similarity	NPC325031
0.7805	Intermediate Similarity	NPC167881
0.7805	Intermediate Similarity	NPC98557
0.7805	Intermediate Similarity	NPC469690
0.7791	Intermediate Similarity	NPC475461
0.7791	Intermediate Similarity	NPC234038
0.7791	Intermediate Similarity	NPC38576
0.7791	Intermediate Similarity	NPC67493
0.7791	Intermediate Similarity	NPC150755
0.7791	Intermediate Similarity	NPC284902
0.7791	Intermediate Similarity	NPC305475
0.7791	Intermediate Similarity	NPC279859
0.7778	Intermediate Similarity	NPC167219
0.7778	Intermediate Similarity	NPC477130
0.7778	Intermediate Similarity	NPC208223
0.7778	Intermediate Similarity	NPC477129
0.7765	Intermediate Similarity	NPC14575
0.7765	Intermediate Similarity	NPC472958
0.7765	Intermediate Similarity	NPC191476
0.7765	Intermediate Similarity	NPC114979
0.7765	Intermediate Similarity	NPC165287
0.7765	Intermediate Similarity	NPC472957
0.7765	Intermediate Similarity	NPC196487
0.7763	Intermediate Similarity	NPC21998
0.7763	Intermediate Similarity	NPC194871
0.7753	Intermediate Similarity	NPC284185
0.7753	Intermediate Similarity	NPC261607
0.7753	Intermediate Similarity	NPC111114
0.7753	Intermediate Similarity	NPC300312
0.775	Intermediate Similarity	NPC244166
0.7738	Intermediate Similarity	NPC471326
0.7738	Intermediate Similarity	NPC221231
0.7738	Intermediate Similarity	NPC85772
0.7738	Intermediate Similarity	NPC475690
0.7733	Intermediate Similarity	NPC133904
0.7711	Intermediate Similarity	NPC6823
0.7711	Intermediate Similarity	NPC73052
0.7711	Intermediate Similarity	NPC290508
0.7711	Intermediate Similarity	NPC474510
0.7711	Intermediate Similarity	NPC293418
0.7701	Intermediate Similarity	NPC478144
0.7701	Intermediate Similarity	NPC475703
0.7701	Intermediate Similarity	NPC237540
0.7701	Intermediate Similarity	NPC72513
0.7701	Intermediate Similarity	NPC160138
0.7692	Intermediate Similarity	NPC273197
0.7692	Intermediate Similarity	NPC90121
0.7692	Intermediate Similarity	NPC193645
0.7692	Intermediate Similarity	NPC275960
0.7692	Intermediate Similarity	NPC475310
0.7692	Intermediate Similarity	NPC234339
0.7692	Intermediate Similarity	NPC48803
0.7683	Intermediate Similarity	NPC471220
0.7674	Intermediate Similarity	NPC38468
0.7674	Intermediate Similarity	NPC99395
0.7674	Intermediate Similarity	NPC319795
0.7674	Intermediate Similarity	NPC255307
0.7674	Intermediate Similarity	NPC197903
0.7674	Intermediate Similarity	NPC50362
0.7654	Intermediate Similarity	NPC40353
0.7654	Intermediate Similarity	NPC473223
0.7647	Intermediate Similarity	NPC22611
0.7647	Intermediate Similarity	NPC16488
0.7647	Intermediate Similarity	NPC474703
0.7647	Intermediate Similarity	NPC40746
0.7647	Intermediate Similarity	NPC59097
0.7647	Intermediate Similarity	NPC170377
0.7647	Intermediate Similarity	NPC169575
0.7647	Intermediate Similarity	NPC193198
0.764	Intermediate Similarity	NPC144133
0.764	Intermediate Similarity	NPC301969
0.764	Intermediate Similarity	NPC469595
0.764	Intermediate Similarity	NPC152467
0.764	Intermediate Similarity	NPC220454
0.764	Intermediate Similarity	NPC251385
0.764	Intermediate Similarity	NPC212679
0.764	Intermediate Similarity	NPC49342
0.764	Intermediate Similarity	NPC179394
0.764	Intermediate Similarity	NPC37607
0.7619	Intermediate Similarity	NPC470241
0.7619	Intermediate Similarity	NPC24417
0.7619	Intermediate Similarity	NPC38642
0.7614	Intermediate Similarity	NPC91248
0.7614	Intermediate Similarity	NPC224652

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 NPC264227 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1486
0.2-0.3	3895
0.3-0.4	2420
0.4-0.5	799
0.5-0.6	305
0.6-0.7	62
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
0.7882	Intermediate Similarity	NPD1694	Approved
0.7692	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5209	Approved
0.7528	Intermediate Similarity	NPD1695	Approved
0.7317	Intermediate Similarity	NPD8039	Approved
0.7253	Intermediate Similarity	NPD5785	Approved
0.7126	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5363	Approved
0.7051	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7154	Phase 3
0.6818	Remote Similarity	NPD5369	Approved
0.6742	Remote Similarity	NPD4270	Approved
0.6742	Remote Similarity	NPD4269	Approved
0.6702	Remote Similarity	NPD6698	Approved
0.6702	Remote Similarity	NPD5207	Approved
0.6702	Remote Similarity	NPD46	Approved
0.6702	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD5362	Discontinued
0.663	Remote Similarity	NPD6684	Approved
0.663	Remote Similarity	NPD5786	Approved
0.663	Remote Similarity	NPD7334	Approved
0.663	Remote Similarity	NPD7146	Approved
0.663	Remote Similarity	NPD6409	Approved
0.663	Remote Similarity	NPD5330	Approved
0.663	Remote Similarity	NPD7521	Approved
0.6602	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6371	Approved
0.6566	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6435	Approved
0.6552	Remote Similarity	NPD4756	Discovery
0.6517	Remote Similarity	NPD4252	Approved
0.6509	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6903	Approved
0.6477	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7983	Approved
0.6421	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6101	Approved
0.64	Remote Similarity	NPD4225	Approved
0.6392	Remote Similarity	NPD5779	Approved
0.6392	Remote Similarity	NPD5778	Approved
0.6344	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5368	Approved
0.6333	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5282	Discontinued
0.6316	Remote Similarity	NPD6672	Approved
0.6316	Remote Similarity	NPD5737	Approved
0.6296	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6411	Approved
0.6289	Remote Similarity	NPD5693	Phase 1
0.6289	Remote Similarity	NPD5694	Approved
0.6262	Remote Similarity	NPD2067	Discontinued
0.6224	Remote Similarity	NPD6399	Phase 3
0.6211	Remote Similarity	NPD3573	Approved
0.62	Remote Similarity	NPD7839	Suspended
0.6186	Remote Similarity	NPD5692	Phase 3
0.6162	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7900	Approved
0.6154	Remote Similarity	NPD4820	Approved
0.6154	Remote Similarity	NPD4819	Approved
0.6154	Remote Similarity	NPD4822	Approved
0.6154	Remote Similarity	NPD4821	Approved
0.6145	Remote Similarity	NPD7331	Phase 2
0.6129	Remote Similarity	NPD5332	Approved
0.6129	Remote Similarity	NPD5331	Approved
0.6122	Remote Similarity	NPD6050	Approved
0.6122	Remote Similarity	NPD5281	Approved
0.6122	Remote Similarity	NPD5284	Approved
0.6111	Remote Similarity	NPD4268	Approved
0.6111	Remote Similarity	NPD4271	Approved
0.6105	Remote Similarity	NPD5279	Phase 3
0.6105	Remote Similarity	NPD4249	Approved
0.61	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4790	Discontinued
0.6082	Remote Similarity	NPD5370	Suspended
0.6071	Remote Similarity	NPD7115	Discovery
0.6042	Remote Similarity	NPD4251	Approved
0.6042	Remote Similarity	NPD4250	Approved
0.6038	Remote Similarity	NPD6008	Approved
0.6023	Remote Similarity	NPD4058	Approved
0.6019	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD28	Approved
0.6	Remote Similarity	NPD6001	Approved
0.6	Remote Similarity	NPD6647	Phase 2
0.6	Remote Similarity	NPD29	Approved
0.6	Remote Similarity	NPD7748	Approved
0.598	Remote Similarity	NPD7902	Approved
0.5979	Remote Similarity	NPD5208	Approved
0.5978	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.596	Remote Similarity	NPD7637	Suspended
0.596	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5695	Phase 3
0.5938	Remote Similarity	NPD6422	Discontinued
0.5938	Remote Similarity	NPD3618	Phase 1
0.5926	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6686	Approved
0.5922	Remote Similarity	NPD7638	Approved
0.5922	Remote Similarity	NPD5696	Approved
0.5918	Remote Similarity	NPD6080	Approved
0.5918	Remote Similarity	NPD6673	Approved
0.5918	Remote Similarity	NPD6904	Approved
0.5909	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD3197	Phase 1
0.5895	Remote Similarity	NPD3666	Approved
0.5895	Remote Similarity	NPD3133	Approved
0.5895	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD3665	Phase 1
0.5882	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD2182	Approved
0.5865	Remote Similarity	NPD7640	Approved
0.5865	Remote Similarity	NPD7639	Approved
0.5859	Remote Similarity	NPD3673	Approved
0.5859	Remote Similarity	NPD3672	Approved
0.5856	Remote Similarity	NPD6053	Discontinued
0.5851	Remote Similarity	NPD3667	Approved
0.5844	Remote Similarity	NPD3172	Approved
0.5843	Remote Similarity	NPD4687	Approved
0.5833	Remote Similarity	NPD1696	Phase 3
0.5833	Remote Similarity	NPD5697	Approved
0.5833	Remote Similarity	NPD7341	Phase 2
0.5825	Remote Similarity	NPD6083	Phase 2
0.5825	Remote Similarity	NPD6084	Phase 2
0.5816	Remote Similarity	NPD4518	Approved
0.5806	Remote Similarity	NPD4695	Discontinued
0.58	Remote Similarity	NPD7515	Phase 2
0.58	Remote Similarity	NPD6079	Approved
0.5795	Remote Similarity	NPD5276	Approved
0.5794	Remote Similarity	NPD5909	Discontinued
0.5789	Remote Similarity	NPD6927	Phase 3
0.5784	Remote Similarity	NPD5654	Approved
0.5783	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.578	Remote Similarity	NPD6899	Approved
0.578	Remote Similarity	NPD6011	Approved
0.578	Remote Similarity	NPD6881	Approved
0.5773	Remote Similarity	NPD6098	Approved
0.5769	Remote Similarity	NPD3196	Approved
0.5769	Remote Similarity	NPD3195	Phase 2
0.5769	Remote Similarity	NPD9298	Approved
0.5769	Remote Similarity	NPD3194	Approved
0.5769	Remote Similarity	NPD4266	Approved
0.5766	Remote Similarity	NPD6650	Approved
0.5766	Remote Similarity	NPD6649	Approved
0.5758	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD7641	Discontinued
0.5729	Remote Similarity	NPD4786	Approved
0.5729	Remote Similarity	NPD3668	Phase 3
0.5727	Remote Similarity	NPD6014	Approved
0.5727	Remote Similarity	NPD6013	Approved
0.5727	Remote Similarity	NPD6012	Approved
0.5726	Remote Similarity	NPD8515	Approved
0.5726	Remote Similarity	NPD8516	Approved
0.5726	Remote Similarity	NPD8513	Phase 3
0.5726	Remote Similarity	NPD8517	Approved
0.5714	Remote Similarity	NPD1238	Approved
0.5714	Remote Similarity	NPD2066	Phase 3
0.5698	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD7260	Phase 2
0.5686	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD4691	Approved
0.5676	Remote Similarity	NPD6883	Approved
0.5676	Remote Similarity	NPD7102	Approved
0.5676	Remote Similarity	NPD7290	Approved
0.5673	Remote Similarity	NPD5959	Approved
0.5667	Remote Similarity	NPD5733	Approved
0.5664	Remote Similarity	NPD7094	Approved
0.5664	Remote Similarity	NPD6858	Approved
0.5663	Remote Similarity	NPD4191	Approved
0.5663	Remote Similarity	NPD4192	Approved
0.5663	Remote Similarity	NPD4193	Approved
0.5663	Remote Similarity	NPD4194	Approved
0.566	Remote Similarity	NPD5344	Discontinued
0.5652	Remote Similarity	NPD7500	Approved
0.5648	Remote Similarity	NPD164	Approved
0.5631	Remote Similarity	NPD4629	Approved
0.5631	Remote Similarity	NPD5210	Approved
0.5631	Remote Similarity	NPD1693	Approved
0.5625	Remote Similarity	NPD8130	Phase 1
0.5625	Remote Similarity	NPD6617	Approved
0.5625	Remote Similarity	NPD6847	Approved
0.5625	Remote Similarity	NPD6869	Approved
0.5612	Remote Similarity	NPD4519	Discontinued
0.5612	Remote Similarity	NPD4694	Approved
0.5612	Remote Similarity	NPD4623	Approved
0.5612	Remote Similarity	NPD5280	Approved
0.5612	Remote Similarity	NPD5690	Phase 2
0.56	Remote Similarity	NPD6051	Approved
0.56	Remote Similarity	NPD5328	Approved
0.56	Remote Similarity	NPD5343	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