NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	272.215
LogP:	2.405
LogD:	1.829
LogS:	-2.779
# Rotatable Bonds:	0
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.67
Synthetic Accessibility Score:	4.713
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.914
MDCK Permeability:	1.1534805707924534e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.771
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.905
Plasma Protein Binding (PPB):	93.88895416259766%
Volume Distribution (VD):	1.042
Pgp-substrate:	9.58757495880127%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.304
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.709
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.761
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.538
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	9.16
Half-life (T1/2):	0.574

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.613
Drug-inuced Liver Injury (DILI):	0.693
AMES Toxicity:	0.113
Rat Oral Acute Toxicity:	0.82
Maximum Recommended Daily Dose:	0.597
Skin Sensitization:	0.521
Carcinogencity:	0.398
Eye Corrosion:	0.004
Eye Irritation:	0.034
Respiratory Toxicity:	0.86

Download Data

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

Natural Product: NPC110022

Natural Product ID:	NPC110022
*Common Name:**	Mairetolide F
IUPAC Name:	(4aR,5S,8R,8aR,9aR)-8,8a-dihydroxy-3,4a,5-trimethyl-5,6,7,8,9,9a-hexahydro-4H-benzo[f][1]benzofuran-2-one
Synonyms:	mairetolide F
Standard InCHIKey:	WWVGDHWKSRNIDY-FAAANYFZSA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-8-4-5-12(16)15(18)7-11-10(6-14(8,15)3)9(2)13(17)19-11/h8,11-12,16,18H,4-7H2,1-3H3/t8-,11+,12+,14+,15-/m0/s1
SMILES:	C[C@H]1CC[C@H]([C@]2(C[C@@H]3C(=C(C)C(=O)O3)C[C@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1099251
PubChem CID:	16091621
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO33420	xylaria sp. bcc 21097	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20155932]

☑ 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
MIC	1

Activity Type	# Activity
Cell Line	4
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	188000.0	nM	PMID[460176]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	188000.0	nM	PMID[460176]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	>	188000.0	nM	PMID[460176]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	188000.0	nM	PMID[460176]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	38000.0	nM	PMID[460176]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	188000.0	nM	PMID[460176]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	188000.0	nM	PMID[460176]

☑ 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 NPC110022 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	211
0.1-0.2	1484
0.2-0.3	4613
0.3-0.4	7966
0.4-0.5	13845
0.5-0.6	7224
0.6-0.7	5834
0.7-0.8	1386
0.8-0.85	97
0.85-0.9	28
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9121	High Similarity	NPC471915
0.9121	High Similarity	NPC111273
0.9111	High Similarity	NPC472640
0.9111	High Similarity	NPC472641
0.9101	High Similarity	NPC472642
0.907	High Similarity	NPC32223
0.9053	High Similarity	NPC474822
0.9	High Similarity	NPC78594
0.875	High Similarity	NPC472552
0.8737	High Similarity	NPC38855
0.8723	High Similarity	NPC199099
0.871	High Similarity	NPC276110
0.8646	High Similarity	NPC11974
0.8646	High Similarity	NPC472554
0.8617	High Similarity	NPC165632
0.8602	High Similarity	NPC105490
0.86	High Similarity	NPC299590
0.8557	High Similarity	NPC471914
0.8556	High Similarity	NPC473891
0.8542	High Similarity	NPC16601
0.8539	High Similarity	NPC253604
0.8511	High Similarity	NPC329435
0.85	High Similarity	NPC181994
0.8495	Intermediate Similarity	NPC7349
0.8469	Intermediate Similarity	NPC471938
0.8469	Intermediate Similarity	NPC23584
0.8444	Intermediate Similarity	NPC131813
0.8438	Intermediate Similarity	NPC278673
0.84	Intermediate Similarity	NPC471205
0.84	Intermediate Similarity	NPC122816
0.84	Intermediate Similarity	NPC187435
0.84	Intermediate Similarity	NPC67321
0.8384	Intermediate Similarity	NPC471937
0.8367	Intermediate Similarity	NPC476081
0.8367	Intermediate Similarity	NPC109195
0.8367	Intermediate Similarity	NPC11956
0.8367	Intermediate Similarity	NPC475038
0.8367	Intermediate Similarity	NPC295791
0.8367	Intermediate Similarity	NPC121423
0.8351	Intermediate Similarity	NPC188968
0.835	Intermediate Similarity	NPC42658
0.8333	Intermediate Similarity	NPC51499
0.8333	Intermediate Similarity	NPC177047
0.8333	Intermediate Similarity	NPC205143
0.8317	Intermediate Similarity	NPC50124
0.8317	Intermediate Similarity	NPC38948
0.83	Intermediate Similarity	NPC471206
0.83	Intermediate Similarity	NPC51719
0.8298	Intermediate Similarity	NPC53555
0.8283	Intermediate Similarity	NPC281378
0.8283	Intermediate Similarity	NPC159533
0.8283	Intermediate Similarity	NPC472821
0.8261	Intermediate Similarity	NPC242448
0.8247	Intermediate Similarity	NPC275086
0.8247	Intermediate Similarity	NPC325229
0.8235	Intermediate Similarity	NPC206618
0.8229	Intermediate Similarity	NPC134072
0.8229	Intermediate Similarity	NPC129569
0.8229	Intermediate Similarity	NPC473153
0.8229	Intermediate Similarity	NPC234993
0.8182	Intermediate Similarity	NPC165250
0.8182	Intermediate Similarity	NPC472815
0.8163	Intermediate Similarity	NPC79303
0.8163	Intermediate Similarity	NPC324841
0.8144	Intermediate Similarity	NPC120446
0.8144	Intermediate Similarity	NPC254121
0.8137	Intermediate Similarity	NPC306265
0.8119	Intermediate Similarity	NPC34768
0.8119	Intermediate Similarity	NPC186668
0.8113	Intermediate Similarity	NPC471816
0.8105	Intermediate Similarity	NPC152778
0.8105	Intermediate Similarity	NPC139692
0.8105	Intermediate Similarity	NPC162615
0.8105	Intermediate Similarity	NPC205034
0.81	Intermediate Similarity	NPC97487
0.81	Intermediate Similarity	NPC165608
0.81	Intermediate Similarity	NPC189588
0.81	Intermediate Similarity	NPC10232
0.81	Intermediate Similarity	NPC45897
0.81	Intermediate Similarity	NPC187302
0.81	Intermediate Similarity	NPC120321
0.81	Intermediate Similarity	NPC120009
0.81	Intermediate Similarity	NPC196471
0.8085	Intermediate Similarity	NPC78973
0.8081	Intermediate Similarity	NPC198992
0.8081	Intermediate Similarity	NPC471412
0.8081	Intermediate Similarity	NPC475617
0.8077	Intermediate Similarity	NPC474846
0.8077	Intermediate Similarity	NPC469656
0.8077	Intermediate Similarity	NPC469655
0.8068	Intermediate Similarity	NPC110373
0.8068	Intermediate Similarity	NPC80471
0.8068	Intermediate Similarity	NPC5908
0.8041	Intermediate Similarity	NPC475380
0.8041	Intermediate Similarity	NPC209297
0.8041	Intermediate Similarity	NPC475304
0.8039	Intermediate Similarity	NPC473586
0.8039	Intermediate Similarity	NPC475074
0.8021	Intermediate Similarity	NPC57117
0.8021	Intermediate Similarity	NPC182826
0.8021	Intermediate Similarity	NPC161998
0.8021	Intermediate Similarity	NPC105375
0.8021	Intermediate Similarity	NPC140277
0.802	Intermediate Similarity	NPC161775
0.8	Intermediate Similarity	NPC162973
0.8	Intermediate Similarity	NPC165578
0.8	Intermediate Similarity	NPC72845
0.8	Intermediate Similarity	NPC473675
0.798	Intermediate Similarity	NPC471413
0.798	Intermediate Similarity	NPC271295
0.798	Intermediate Similarity	NPC47024
0.798	Intermediate Similarity	NPC272223
0.7979	Intermediate Similarity	NPC82876
0.7961	Intermediate Similarity	NPC475263
0.7961	Intermediate Similarity	NPC88701
0.7961	Intermediate Similarity	NPC472439
0.7961	Intermediate Similarity	NPC469916
0.7959	Intermediate Similarity	NPC473244
0.7959	Intermediate Similarity	NPC100912
0.7959	Intermediate Similarity	NPC311241
0.7959	Intermediate Similarity	NPC210337
0.7959	Intermediate Similarity	NPC475446
0.7959	Intermediate Similarity	NPC287668
0.7957	Intermediate Similarity	NPC471779
0.7941	Intermediate Similarity	NPC220217
0.7941	Intermediate Similarity	NPC88349
0.7941	Intermediate Similarity	NPC119855
0.7941	Intermediate Similarity	NPC477090
0.7941	Intermediate Similarity	NPC239961
0.7938	Intermediate Similarity	NPC86893
0.7938	Intermediate Similarity	NPC292178
0.7925	Intermediate Similarity	NPC478212
0.7921	Intermediate Similarity	NPC61442
0.7921	Intermediate Similarity	NPC474124
0.7921	Intermediate Similarity	NPC160583
0.7921	Intermediate Similarity	NPC72842
0.7921	Intermediate Similarity	NPC473523
0.7917	Intermediate Similarity	NPC472812
0.7912	Intermediate Similarity	NPC311070
0.7905	Intermediate Similarity	NPC470076
0.79	Intermediate Similarity	NPC295110
0.79	Intermediate Similarity	NPC247701
0.79	Intermediate Similarity	NPC222875
0.79	Intermediate Similarity	NPC25177
0.79	Intermediate Similarity	NPC268829
0.7895	Intermediate Similarity	NPC310479
0.7895	Intermediate Similarity	NPC221111
0.7895	Intermediate Similarity	NPC209816
0.7895	Intermediate Similarity	NPC280149
0.7885	Intermediate Similarity	NPC478210
0.7885	Intermediate Similarity	NPC475586
0.7885	Intermediate Similarity	NPC322912
0.7885	Intermediate Similarity	NPC257853
0.7879	Intermediate Similarity	NPC72647
0.7879	Intermediate Similarity	NPC159763
0.7879	Intermediate Similarity	NPC278386
0.7879	Intermediate Similarity	NPC222303
0.7879	Intermediate Similarity	NPC124512
0.7879	Intermediate Similarity	NPC107806
0.7879	Intermediate Similarity	NPC216478
0.7872	Intermediate Similarity	NPC93411
0.787	Intermediate Similarity	NPC13713
0.787	Intermediate Similarity	NPC58662
0.7864	Intermediate Similarity	NPC319438
0.7864	Intermediate Similarity	NPC302788
0.7864	Intermediate Similarity	NPC179380
0.7864	Intermediate Similarity	NPC216636
0.7857	Intermediate Similarity	NPC211810
0.7857	Intermediate Similarity	NPC471765
0.7857	Intermediate Similarity	NPC472995
0.7857	Intermediate Similarity	NPC202833
0.7857	Intermediate Similarity	NPC242848
0.7857	Intermediate Similarity	NPC194132
0.7857	Intermediate Similarity	NPC221801
0.7857	Intermediate Similarity	NPC88009
0.7857	Intermediate Similarity	NPC93245
0.7857	Intermediate Similarity	NPC16967
0.7857	Intermediate Similarity	NPC284194
0.7849	Intermediate Similarity	NPC475069
0.7849	Intermediate Similarity	NPC175145
0.7849	Intermediate Similarity	NPC471219
0.7843	Intermediate Similarity	NPC296950
0.7843	Intermediate Similarity	NPC473543
0.7841	Intermediate Similarity	NPC189206
0.7835	Intermediate Similarity	NPC225474
0.7835	Intermediate Similarity	NPC148000
0.7835	Intermediate Similarity	NPC469596
0.7835	Intermediate Similarity	NPC191521
0.783	Intermediate Similarity	NPC472002
0.783	Intermediate Similarity	NPC470063
0.7826	Intermediate Similarity	NPC102048
0.7822	Intermediate Similarity	NPC470972
0.7822	Intermediate Similarity	NPC475344
0.7822	Intermediate Similarity	NPC258547
0.7822	Intermediate Similarity	NPC476471
0.7822	Intermediate Similarity	NPC58329
0.7822	Intermediate Similarity	NPC273668
0.7822	Intermediate Similarity	NPC283343
0.7812	Intermediate Similarity	NPC249034
0.7812	Intermediate Similarity	NPC472811

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 NPC110022 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1820
0.2-0.3	3810
0.3-0.4	2182
0.4-0.5	756
0.5-0.6	246
0.6-0.7	134
0.7-0.8	21
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
0.86	High Similarity	NPD4061	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7638	Approved
0.7879	Intermediate Similarity	NPD4225	Approved
0.7864	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD7640	Approved
0.78	Intermediate Similarity	NPD7639	Approved
0.7727	Intermediate Similarity	NPD7516	Approved
0.7723	Intermediate Similarity	NPD5344	Discontinued
0.7647	Intermediate Similarity	NPD7632	Discontinued
0.7636	Intermediate Similarity	NPD7328	Approved
0.7636	Intermediate Similarity	NPD7327	Approved
0.7619	Intermediate Similarity	NPD6686	Approved
0.7434	Intermediate Similarity	NPD8379	Approved
0.7434	Intermediate Similarity	NPD8335	Approved
0.7434	Intermediate Similarity	NPD8378	Approved
0.7434	Intermediate Similarity	NPD8296	Approved
0.7434	Intermediate Similarity	NPD8380	Approved
0.7345	Intermediate Similarity	NPD8377	Approved
0.7345	Intermediate Similarity	NPD8294	Approved
0.7282	Intermediate Similarity	NPD6648	Approved
0.7281	Intermediate Similarity	NPD8033	Approved
0.7179	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD7319	Approved
0.713	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7503	Approved
0.693	Remote Similarity	NPD7115	Discovery
0.6909	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7524	Approved
0.6832	Remote Similarity	NPD46	Approved
0.6832	Remote Similarity	NPD7838	Discovery
0.6832	Remote Similarity	NPD6698	Approved
0.6814	Remote Similarity	NPD4632	Approved
0.6789	Remote Similarity	NPD5739	Approved
0.6789	Remote Similarity	NPD6675	Approved
0.6789	Remote Similarity	NPD7128	Approved
0.6789	Remote Similarity	NPD6402	Approved
0.6765	Remote Similarity	NPD7637	Suspended
0.6752	Remote Similarity	NPD6319	Approved
0.6735	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD4159	Approved
0.6727	Remote Similarity	NPD5697	Approved
0.6727	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6635	Remote Similarity	NPD7748	Approved
0.6633	Remote Similarity	NPD6695	Phase 3
0.6607	Remote Similarity	NPD6014	Approved
0.6607	Remote Similarity	NPD6013	Approved
0.6607	Remote Similarity	NPD6372	Approved
0.6607	Remote Similarity	NPD6373	Approved
0.6607	Remote Similarity	NPD6012	Approved
0.6604	Remote Similarity	NPD7902	Approved
0.6602	Remote Similarity	NPD7515	Phase 2
0.6579	Remote Similarity	NPD8297	Approved
0.6577	Remote Similarity	NPD6412	Phase 2
0.6566	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6883	Approved
0.6549	Remote Similarity	NPD7102	Approved
0.6549	Remote Similarity	NPD7290	Approved
0.6549	Remote Similarity	NPD6371	Approved
0.6518	Remote Similarity	NPD6011	Approved
0.6496	Remote Similarity	NPD6009	Approved
0.6495	Remote Similarity	NPD7525	Registered
0.6491	Remote Similarity	NPD8130	Phase 1
0.6491	Remote Similarity	NPD6617	Approved
0.6491	Remote Similarity	NPD6869	Approved
0.6491	Remote Similarity	NPD6649	Approved
0.6491	Remote Similarity	NPD6847	Approved
0.6491	Remote Similarity	NPD6650	Approved
0.6486	Remote Similarity	NPD6008	Approved
0.6449	Remote Similarity	NPD6084	Phase 2
0.6449	Remote Similarity	NPD4755	Approved
0.6449	Remote Similarity	NPD6083	Phase 2
0.6436	Remote Similarity	NPD3618	Phase 1
0.6435	Remote Similarity	NPD6882	Approved
0.6435	Remote Similarity	NPD6053	Discontinued
0.6417	Remote Similarity	NPD5983	Phase 2
0.6417	Remote Similarity	NPD6921	Approved
0.6408	Remote Similarity	NPD6051	Approved
0.6404	Remote Similarity	NPD4634	Approved
0.6393	Remote Similarity	NPD7492	Approved
0.6389	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4202	Approved
0.6381	Remote Similarity	NPD6399	Phase 3
0.6373	Remote Similarity	NPD7750	Discontinued
0.6364	Remote Similarity	NPD5211	Phase 2
0.6356	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6616	Approved
0.6333	Remote Similarity	NPD6059	Approved
0.6333	Remote Similarity	NPD6054	Approved
0.633	Remote Similarity	NPD5286	Approved
0.633	Remote Similarity	NPD5285	Approved
0.633	Remote Similarity	NPD4696	Approved
0.633	Remote Similarity	NPD4700	Approved
0.6327	Remote Similarity	NPD6930	Phase 2
0.6327	Remote Similarity	NPD6931	Approved
0.6321	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7900	Approved
0.6311	Remote Similarity	NPD7604	Phase 2
0.6311	Remote Similarity	NPD8328	Phase 3
0.6292	Remote Similarity	NPD371	Approved
0.629	Remote Similarity	NPD7078	Approved
0.629	Remote Similarity	NPD8293	Discontinued
0.6286	Remote Similarity	NPD8035	Phase 2
0.6286	Remote Similarity	NPD8034	Phase 2
0.6283	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6015	Approved
0.6281	Remote Similarity	NPD6016	Approved
0.6271	Remote Similarity	NPD6274	Approved
0.6262	Remote Similarity	NPD5695	Phase 3
0.6262	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD5328	Approved
0.624	Remote Similarity	NPD7736	Approved
0.6239	Remote Similarity	NPD5696	Approved
0.623	Remote Similarity	NPD5988	Approved
0.623	Remote Similarity	NPD6370	Approved
0.6226	Remote Similarity	NPD5779	Approved
0.6226	Remote Similarity	NPD5778	Approved
0.6224	Remote Similarity	NPD6929	Approved
0.6224	Remote Similarity	NPD7645	Phase 2
0.6216	Remote Similarity	NPD5224	Approved
0.6216	Remote Similarity	NPD5225	Approved
0.6216	Remote Similarity	NPD5226	Approved
0.6216	Remote Similarity	NPD4633	Approved
0.621	Remote Similarity	NPD6336	Discontinued
0.619	Remote Similarity	NPD3168	Discontinued
0.6176	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7514	Phase 3
0.6162	Remote Similarity	NPD7332	Phase 2
0.6161	Remote Similarity	NPD5175	Approved
0.6161	Remote Similarity	NPD5174	Approved
0.6132	Remote Similarity	NPD7087	Discontinued
0.6132	Remote Similarity	NPD5693	Phase 1
0.6132	Remote Similarity	NPD6079	Approved
0.6126	Remote Similarity	NPD5223	Approved
0.6122	Remote Similarity	NPD6697	Approved
0.6122	Remote Similarity	NPD6118	Approved
0.6122	Remote Similarity	NPD6115	Approved
0.6122	Remote Similarity	NPD6114	Approved
0.6117	Remote Similarity	NPD6409	Approved
0.6117	Remote Similarity	NPD7334	Approved
0.6117	Remote Similarity	NPD5330	Approved
0.6117	Remote Similarity	NPD7146	Approved
0.6117	Remote Similarity	NPD6684	Approved
0.6117	Remote Similarity	NPD7521	Approved
0.6116	Remote Similarity	NPD7100	Approved
0.6116	Remote Similarity	NPD7101	Approved
0.6095	Remote Similarity	NPD4753	Phase 2
0.6083	Remote Similarity	NPD6317	Approved
0.6082	Remote Similarity	NPD6933	Approved
0.6078	Remote Similarity	NPD3133	Approved
0.6078	Remote Similarity	NPD3665	Phase 1
0.6078	Remote Similarity	NPD3666	Approved
0.6068	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD3573	Approved
0.6058	Remote Similarity	NPD7625	Phase 1
0.6058	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD4697	Phase 3
0.6055	Remote Similarity	NPD5222	Approved
0.6055	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5221	Approved
0.6053	Remote Similarity	NPD4768	Approved
0.6053	Remote Similarity	NPD4767	Approved
0.604	Remote Similarity	NPD3667	Approved
0.6033	Remote Similarity	NPD6313	Approved
0.6033	Remote Similarity	NPD6314	Approved
0.6033	Remote Similarity	NPD6335	Approved
0.602	Remote Similarity	NPD6925	Approved
0.602	Remote Similarity	NPD5776	Phase 2
0.602	Remote Similarity	NPD6932	Approved
0.602	Remote Similarity	NPD6116	Phase 1
0.6019	Remote Similarity	NPD5282	Discontinued
0.6019	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6893	Approved
0.6018	Remote Similarity	NPD4754	Approved
0.6016	Remote Similarity	NPD8517	Approved
0.6016	Remote Similarity	NPD6909	Approved
0.6016	Remote Similarity	NPD8513	Phase 3
0.6016	Remote Similarity	NPD8515	Approved
0.6016	Remote Similarity	NPD6908	Approved
0.6016	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6903	Approved
0.5981	Remote Similarity	NPD7983	Approved
0.5981	Remote Similarity	NPD6411	Approved
0.5963	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD4249	Approved
0.596	Remote Similarity	NPD7145	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