NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	360.19
Volume:	388.712
LogP:	5.345
LogD:	3.664
LogS:	-3.351
# Rotatable Bonds:	10
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	3.2
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.929
MDCK Permeability:	6.873980055388529e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.076
20% Bioavailability (F20%):	0.922
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	97.41109466552734%
Volume Distribution (VD):	0.415
Pgp-substrate:	2.122286081314087%

ADMET: Metabolism

CYP1A2-inhibitor:	0.157
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.511
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.153
CYP2D6-substrate:	0.247
CYP3A4-inhibitor:	0.074
CYP3A4-substrate:	0.057

ADMET: Excretion

Clearance (CL):	13.451
Half-life (T1/2):	0.864

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.722
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.675
Carcinogencity:	0.615
Eye Corrosion:	0.014
Eye Irritation:	0.475
Respiratory Toxicity:	0.265

Download Data

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

Natural Product: NPC477153

Natural Product ID:	NPC477153
*Common Name:**	Fornicin C
IUPAC Name:	(5E)-2-[2-(2,5-dihydroxyphenyl)-2-oxoethyl]-6,10-dimethylundeca-5,9-dienoic acid
Synonyms:	fornicin C
Standard InCHIKey:	PNXHXPQJFNVWQM-OVCLIPMQSA-N
Standard InCHI:	InChI=1S/C21H28O5/c1-14(2)6-4-7-15(3)8-5-9-16(21(25)26)12-20(24)18-13-17(22)10-11-19(18)23/h6,8,10-11,13,16,22-23H,4-5,7,9,12H2,1-3H3,(H,25,26)/b15-8+
SMILES:	CC(=CCC/C(=C/CCC(CC(=O)C1=C(C=CC(=C1)O)O)C(=O)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	16086602
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO21422	Ganoderma fornicatum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[16989537]
NPO21422	Ganoderma fornicatum	Species	Ganodermataceae	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
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	=	23	ug/ml	PMID[16989537]

☑ 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 NPC477153 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	270
0.1-0.2	1404
0.2-0.3	3702
0.3-0.4	9411
0.4-0.5	10081
0.5-0.6	6063
0.6-0.7	9306
0.7-0.8	2197
0.8-0.85	175
0.85-0.9	80
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9397	High Similarity	NPC269414
0.9224	High Similarity	NPC240163
0.9106	High Similarity	NPC306765
0.9068	High Similarity	NPC160199
0.8983	High Similarity	NPC312800
0.8898	High Similarity	NPC161304
0.8879	High Similarity	NPC228609
0.8852	High Similarity	NPC25168
0.8824	High Similarity	NPC477453
0.877	High Similarity	NPC159760
0.877	High Similarity	NPC178395
0.877	High Similarity	NPC301987
0.877	High Similarity	NPC222876
0.877	High Similarity	NPC179092
0.877	High Similarity	NPC35856
0.877	High Similarity	NPC244994
0.877	High Similarity	NPC272454
0.877	High Similarity	NPC165197
0.877	High Similarity	NPC115188
0.877	High Similarity	NPC26433
0.877	High Similarity	NPC292665
0.876	High Similarity	NPC233165
0.876	High Similarity	NPC232178
0.876	High Similarity	NPC184579
0.8722	High Similarity	NPC42262
0.8722	High Similarity	NPC32749
0.8722	High Similarity	NPC220496
0.8722	High Similarity	NPC147542
0.8722	High Similarity	NPC37992
0.8722	High Similarity	NPC327916
0.8722	High Similarity	NPC241349
0.872	High Similarity	NPC287473
0.8682	High Similarity	NPC110609
0.8682	High Similarity	NPC242358
0.8682	High Similarity	NPC246693
0.8678	High Similarity	NPC41567
0.8655	High Similarity	NPC197513
0.8655	High Similarity	NPC114918
0.8651	High Similarity	NPC96915
0.8647	High Similarity	NPC471602
0.8647	High Similarity	NPC256463
0.8647	High Similarity	NPC29771
0.8647	High Similarity	NPC111422
0.8647	High Similarity	NPC306835
0.8647	High Similarity	NPC216312
0.8647	High Similarity	NPC476477
0.8647	High Similarity	NPC299405
0.864	High Similarity	NPC117794
0.8629	High Similarity	NPC68167
0.8629	High Similarity	NPC297193
0.8621	High Similarity	NPC224584
0.8595	High Similarity	NPC125252
0.8583	High Similarity	NPC471530
0.8583	High Similarity	NPC71525
0.8571	High Similarity	NPC472592
0.8571	High Similarity	NPC167055
0.8571	High Similarity	NPC240744
0.8561	High Similarity	NPC472308
0.8561	High Similarity	NPC272268
0.856	High Similarity	NPC275145
0.8537	High Similarity	NPC206778
0.8537	High Similarity	NPC285829
0.8534	High Similarity	NPC34715
0.8527	High Similarity	NPC31539
0.8519	High Similarity	NPC257003
0.8519	High Similarity	NPC471444
0.8512	High Similarity	NPC108288
0.8504	High Similarity	NPC136342
0.8504	High Similarity	NPC295202
0.8504	High Similarity	NPC3224
0.8504	High Similarity	NPC227741
0.8504	High Similarity	NPC49647
0.8504	High Similarity	NPC473751
0.85	High Similarity	NPC163154
0.8492	Intermediate Similarity	NPC310540
0.8485	Intermediate Similarity	NPC29317
0.8485	Intermediate Similarity	NPC176102
0.8485	Intermediate Similarity	NPC204257
0.8485	Intermediate Similarity	NPC229638
0.8485	Intermediate Similarity	NPC22222
0.8485	Intermediate Similarity	NPC281513
0.8485	Intermediate Similarity	NPC71108
0.8485	Intermediate Similarity	NPC267539
0.8485	Intermediate Similarity	NPC254832
0.848	Intermediate Similarity	NPC307174
0.848	Intermediate Similarity	NPC244351
0.8462	Intermediate Similarity	NPC205992
0.8456	Intermediate Similarity	NPC474300
0.8448	Intermediate Similarity	NPC187913
0.8425	Intermediate Similarity	NPC131799
0.8417	Intermediate Similarity	NPC211421
0.8413	Intermediate Similarity	NPC375356
0.8394	Intermediate Similarity	NPC476473
0.8387	Intermediate Similarity	NPC260837
0.8372	Intermediate Similarity	NPC48248
0.8359	Intermediate Similarity	NPC1991
0.8359	Intermediate Similarity	NPC51037
0.8359	Intermediate Similarity	NPC231774
0.8358	Intermediate Similarity	NPC245923
0.8347	Intermediate Similarity	NPC81808
0.8346	Intermediate Similarity	NPC234890
0.8346	Intermediate Similarity	NPC74507
0.8346	Intermediate Similarity	NPC161632
0.8333	Intermediate Similarity	NPC300274
0.8333	Intermediate Similarity	NPC157478
0.8333	Intermediate Similarity	NPC274085
0.8333	Intermediate Similarity	NPC295406
0.8333	Intermediate Similarity	NPC89664
0.8333	Intermediate Similarity	NPC289572
0.8333	Intermediate Similarity	NPC283514
0.8333	Intermediate Similarity	NPC115458
0.8333	Intermediate Similarity	NPC200422
0.8321	Intermediate Similarity	NPC7012
0.8319	Intermediate Similarity	NPC208229
0.8308	Intermediate Similarity	NPC34414
0.8308	Intermediate Similarity	NPC278928
0.8308	Intermediate Similarity	NPC146647
0.8308	Intermediate Similarity	NPC109123
0.8305	Intermediate Similarity	NPC279887
0.8305	Intermediate Similarity	NPC100551
0.8305	Intermediate Similarity	NPC68260
0.8295	Intermediate Similarity	NPC209959
0.8293	Intermediate Similarity	NPC121259
0.8284	Intermediate Similarity	NPC155211
0.8284	Intermediate Similarity	NPC474813
0.8281	Intermediate Similarity	NPC103540
0.8276	Intermediate Similarity	NPC93831
0.8271	Intermediate Similarity	NPC288089
0.8258	Intermediate Similarity	NPC118253
0.8258	Intermediate Similarity	NPC58685
0.8254	Intermediate Similarity	NPC198336
0.8244	Intermediate Similarity	NPC123
0.8244	Intermediate Similarity	NPC55949
0.8244	Intermediate Similarity	NPC163169
0.8244	Intermediate Similarity	NPC17840
0.8244	Intermediate Similarity	NPC247477
0.824	Intermediate Similarity	NPC216297
0.824	Intermediate Similarity	NPC473662
0.824	Intermediate Similarity	NPC72977
0.824	Intermediate Similarity	NPC7151
0.8235	Intermediate Similarity	NPC295339
0.8235	Intermediate Similarity	NPC282855
0.8235	Intermediate Similarity	NPC26013
0.8231	Intermediate Similarity	NPC237225
0.8231	Intermediate Similarity	NPC95537
0.8231	Intermediate Similarity	NPC282923
0.8226	Intermediate Similarity	NPC474890
0.8226	Intermediate Similarity	NPC161943
0.8226	Intermediate Similarity	NPC273282
0.8217	Intermediate Similarity	NPC474944
0.8211	Intermediate Similarity	NPC128825
0.8203	Intermediate Similarity	NPC4012
0.8203	Intermediate Similarity	NPC142956
0.8195	Intermediate Similarity	NPC472591
0.8195	Intermediate Similarity	NPC43627
0.819	Intermediate Similarity	NPC13426
0.8189	Intermediate Similarity	NPC46634
0.8182	Intermediate Similarity	NPC141549
0.8182	Intermediate Similarity	NPC85342
0.8182	Intermediate Similarity	NPC244699
0.8175	Intermediate Similarity	NPC225243
0.8175	Intermediate Similarity	NPC315578
0.8168	Intermediate Similarity	NPC99731
0.8162	Intermediate Similarity	NPC4214
0.8162	Intermediate Similarity	NPC61590
0.816	Intermediate Similarity	NPC328459
0.816	Intermediate Similarity	NPC90522
0.8156	Intermediate Similarity	NPC61284
0.8156	Intermediate Similarity	NPC113428
0.8148	Intermediate Similarity	NPC474726
0.8148	Intermediate Similarity	NPC475955
0.8134	Intermediate Similarity	NPC474097
0.8115	Intermediate Similarity	NPC296144
0.8115	Intermediate Similarity	NPC28784
0.8115	Intermediate Similarity	NPC242136
0.8112	Intermediate Similarity	NPC315520
0.8106	Intermediate Similarity	NPC198305
0.8106	Intermediate Similarity	NPC199253
0.8106	Intermediate Similarity	NPC7569
0.8106	Intermediate Similarity	NPC136588
0.8106	Intermediate Similarity	NPC278787
0.8102	Intermediate Similarity	NPC26924
0.8092	Intermediate Similarity	NPC476024
0.8092	Intermediate Similarity	NPC165257
0.8088	Intermediate Similarity	NPC305060
0.8085	Intermediate Similarity	NPC308799
0.8083	Intermediate Similarity	NPC98392
0.8083	Intermediate Similarity	NPC95172
0.808	Intermediate Similarity	NPC94637
0.8077	Intermediate Similarity	NPC8745
0.8074	Intermediate Similarity	NPC283088
0.8071	Intermediate Similarity	NPC103910
0.8067	Intermediate Similarity	NPC141523
0.8065	Intermediate Similarity	NPC83718
0.8062	Intermediate Similarity	NPC265910
0.8062	Intermediate Similarity	NPC68756
0.8062	Intermediate Similarity	NPC236189
0.8062	Intermediate Similarity	NPC91475
0.8062	Intermediate Similarity	NPC152525
0.806	Intermediate Similarity	NPC53896

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 NPC477153 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	905
0.2-0.3	1527
0.3-0.4	2620
0.4-0.5	2185
0.5-0.6	1127
0.6-0.7	439
0.7-0.8	70
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8512	High Similarity	NPD405	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD2935	Discontinued
0.8305	Intermediate Similarity	NPD9266	Approved
0.8305	Intermediate Similarity	NPD74	Approved
0.8281	Intermediate Similarity	NPD1470	Approved
0.822	Intermediate Similarity	NPD9264	Approved
0.822	Intermediate Similarity	NPD9267	Approved
0.822	Intermediate Similarity	NPD9263	Approved
0.8211	Intermediate Similarity	NPD9493	Approved
0.7969	Intermediate Similarity	NPD1201	Approved
0.7903	Intermediate Similarity	NPD9281	Approved
0.7883	Intermediate Similarity	NPD2799	Discontinued
0.7881	Intermediate Similarity	NPD9261	Approved
0.7863	Intermediate Similarity	NPD1164	Approved
0.7836	Intermediate Similarity	NPD2313	Discontinued
0.7803	Intermediate Similarity	NPD2798	Approved
0.7794	Intermediate Similarity	NPD447	Suspended
0.777	Intermediate Similarity	NPD2346	Discontinued
0.7769	Intermediate Similarity	NPD9717	Approved
0.7721	Intermediate Similarity	NPD943	Approved
0.7698	Intermediate Similarity	NPD5408	Approved
0.7698	Intermediate Similarity	NPD5405	Approved
0.7698	Intermediate Similarity	NPD5406	Approved
0.7698	Intermediate Similarity	NPD5404	Approved
0.7626	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1203	Approved
0.7574	Intermediate Similarity	NPD411	Approved
0.7563	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3300	Phase 2
0.7419	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2344	Approved
0.7385	Intermediate Similarity	NPD9545	Approved
0.7373	Intermediate Similarity	NPD844	Approved
0.7368	Intermediate Similarity	NPD9269	Phase 2
0.7348	Intermediate Similarity	NPD3496	Discontinued
0.7343	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD9268	Approved
0.7319	Intermediate Similarity	NPD3764	Approved
0.7311	Intermediate Similarity	NPD288	Approved
0.7299	Intermediate Similarity	NPD6832	Phase 2
0.7295	Intermediate Similarity	NPD1929	Approved
0.7295	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1930	Approved
0.7286	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3019	Approved
0.7273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2932	Approved
0.7266	Intermediate Similarity	NPD520	Approved
0.7241	Intermediate Similarity	NPD9258	Approved
0.7241	Intermediate Similarity	NPD9256	Approved
0.7214	Intermediate Similarity	NPD1240	Approved
0.7211	Intermediate Similarity	NPD7390	Discontinued
0.7206	Intermediate Similarity	NPD2797	Approved
0.7194	Intermediate Similarity	NPD3268	Approved
0.7192	Intermediate Similarity	NPD2309	Approved
0.719	Intermediate Similarity	NPD5402	Approved
0.719	Intermediate Similarity	NPD2066	Phase 3
0.7188	Intermediate Similarity	NPD7635	Approved
0.7163	Intermediate Similarity	NPD230	Phase 1
0.7162	Intermediate Similarity	NPD2532	Approved
0.7162	Intermediate Similarity	NPD2534	Approved
0.7162	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2533	Approved
0.7153	Intermediate Similarity	NPD1019	Discontinued
0.7143	Intermediate Similarity	NPD2182	Approved
0.7133	Intermediate Similarity	NPD4308	Phase 3
0.7133	Intermediate Similarity	NPD1510	Phase 2
0.7124	Intermediate Similarity	NPD2801	Approved
0.7121	Intermediate Similarity	NPD1759	Phase 1
0.7113	Intermediate Similarity	NPD1607	Approved
0.7107	Intermediate Similarity	NPD7473	Discontinued
0.7097	Intermediate Similarity	NPD164	Approved
0.7087	Intermediate Similarity	NPD1317	Discontinued
0.7083	Intermediate Similarity	NPD1551	Phase 2
0.7077	Intermediate Similarity	NPD5951	Approved
0.7073	Intermediate Similarity	NPD1932	Approved
0.7059	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6844	Discontinued
0.7059	Intermediate Similarity	NPD845	Approved
0.7055	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3020	Approved
0.7047	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1758	Phase 1
0.7037	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6232	Discontinued
0.7023	Intermediate Similarity	NPD255	Approved
0.7023	Intermediate Similarity	NPD6671	Approved
0.7023	Intermediate Similarity	NPD256	Approved
0.7015	Intermediate Similarity	NPD4626	Approved
0.7014	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7819	Suspended
0.7008	Intermediate Similarity	NPD2329	Discontinued
0.7007	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7003	Approved
0.7007	Intermediate Similarity	NPD8166	Discontinued
0.7007	Intermediate Similarity	NPD3750	Approved
0.6985	Remote Similarity	NPD1481	Phase 2
0.6985	Remote Similarity	NPD1608	Approved
0.696	Remote Similarity	NPD1237	Approved
0.6953	Remote Similarity	NPD4750	Phase 3
0.6953	Remote Similarity	NPD3022	Approved
0.6953	Remote Similarity	NPD3021	Approved
0.6942	Remote Similarity	NPD2859	Approved
0.6942	Remote Similarity	NPD2860	Approved
0.6934	Remote Similarity	NPD1755	Approved
0.6917	Remote Similarity	NPD1202	Approved
0.6912	Remote Similarity	NPD1535	Discovery
0.6908	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD257	Approved
0.6906	Remote Similarity	NPD258	Approved
0.6903	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6663	Approved
0.6899	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD9259	Approved
0.6897	Remote Similarity	NPD9257	Approved
0.6884	Remote Similarity	NPD1283	Approved
0.6884	Remote Similarity	NPD1876	Approved
0.6883	Remote Similarity	NPD7411	Suspended
0.6883	Remote Similarity	NPD2672	Discontinued
0.6879	Remote Similarity	NPD7075	Discontinued
0.6871	Remote Similarity	NPD1549	Phase 2
0.6867	Remote Similarity	NPD6799	Approved
0.6867	Remote Similarity	NPD1511	Approved
0.6864	Remote Similarity	NPD800	Approved
0.6863	Remote Similarity	NPD7458	Discontinued
0.6863	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2933	Approved
0.686	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1693	Approved
0.686	Remote Similarity	NPD2934	Approved
0.6857	Remote Similarity	NPD5736	Approved
0.6857	Remote Similarity	NPD9494	Approved
0.6853	Remote Similarity	NPD4307	Phase 2
0.6839	Remote Similarity	NPD1934	Approved
0.6838	Remote Similarity	NPD3023	Approved
0.6838	Remote Similarity	NPD3026	Approved
0.6835	Remote Similarity	NPD3266	Approved
0.6835	Remote Similarity	NPD3267	Approved
0.6821	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2629	Approved
0.6818	Remote Similarity	NPD4380	Phase 2
0.6818	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3882	Suspended
0.6815	Remote Similarity	NPD7768	Phase 2
0.6815	Remote Similarity	NPD3024	Approved
0.6815	Remote Similarity	NPD3025	Approved
0.6807	Remote Similarity	NPD1090	Approved
0.6807	Remote Similarity	NPD1089	Approved
0.6807	Remote Similarity	NPD1086	Approved
0.6806	Remote Similarity	NPD1933	Approved
0.6803	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.68	Remote Similarity	NPD846	Approved
0.68	Remote Similarity	NPD940	Approved
0.6795	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5277	Phase 2
0.6786	Remote Similarity	NPD8150	Discontinued
0.6786	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5647	Approved
0.6779	Remote Similarity	NPD1196	Approved
0.6779	Remote Similarity	NPD4628	Phase 3
0.6776	Remote Similarity	NPD1512	Approved
0.6772	Remote Similarity	NPD3749	Approved
0.6765	Remote Similarity	NPD1778	Approved
0.6765	Remote Similarity	NPD17	Approved
0.6765	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1543	Discontinued
0.6752	Remote Similarity	NPD3817	Phase 2
0.6746	Remote Similarity	NPD6647	Phase 2
0.6739	Remote Similarity	NPD3972	Approved
0.6736	Remote Similarity	NPD825	Approved
0.6736	Remote Similarity	NPD826	Approved
0.6735	Remote Similarity	NPD2796	Approved
0.6733	Remote Similarity	NPD6190	Approved
0.6732	Remote Similarity	NPD5403	Approved
0.6725	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1444	Approved
0.6719	Remote Similarity	NPD1445	Approved
0.6716	Remote Similarity	NPD9568	Approved
0.6712	Remote Similarity	NPD9279	Approved
0.6711	Remote Similarity	NPD2800	Approved
0.6711	Remote Similarity	NPD1195	Approved
0.671	Remote Similarity	NPD6599	Discontinued
0.6709	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD8313	Approved
0.6707	Remote Similarity	NPD8312	Approved
0.6706	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD9495	Approved
0.6694	Remote Similarity	NPD1088	Approved
0.6693	Remote Similarity	NPD5909	Discontinued
0.6691	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD5691	Approved
0.669	Remote Similarity	NPD6355	Discontinued
0.6689	Remote Similarity	NPD1471	Phase 3
0.6687	Remote Similarity	NPD5494	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