NPASS Compound

Structure

CID193203 OpenBabel06191715582D 30 32 0 0 1 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 15 1 0 0 0 0 6 16 1 0 0 0 0 7 10 1 0 0 0 0 7 18 2 0 0 0 0 8 12 1 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 21 2 0 0 0 0 12 22 1 0 0 0 0 13 23 2 0 0 0 0 14 24 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 19 22 2 0 0 0 0 20 23 1 0 0 0 0 21 25 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 26 1 0 0 0 0 24 27 1 6 0 0 0 25 29 1 0 0 0 0 25 30 2 0 0 0 0 27 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.28
Volume:	460.431
LogP:	7.011
LogD:	5.022
LogS:	-3.539
# Rotatable Bonds:	6
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.484
Synthetic Accessibility Score:	3.707
Fsp3:	0.593
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.118
MDCK Permeability:	2.097297510772478e-05
Pgp-inhibitor:	0.368
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.346
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	97.27246856689453%
Volume Distribution (VD):	0.515
Pgp-substrate:	0.5966699719429016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.489
CYP2C19-inhibitor:	0.125
CYP2C19-substrate:	0.132
CYP2C9-inhibitor:	0.285
CYP2C9-substrate:	0.61
CYP2D6-inhibitor:	0.635
CYP2D6-substrate:	0.147
CYP3A4-inhibitor:	0.123
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	3.874
Half-life (T1/2):	0.295

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.41
Drug-inuced Liver Injury (DILI):	0.1
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.389
Skin Sensitization:	0.306
Carcinogencity:	0.045
Eye Corrosion:	0.008
Eye Irritation:	0.248
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC193203

Natural Product ID:	NPC193203
*Common Name:**	(+)-Subersic Acid
IUPAC Name:	3-[(E)-5-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpent-2-enyl]-4-hydroxybenzoic acid
Synonyms:	(+)-Subersic Acid
Standard InCHIKey:	RIYHRKNIDKXDII-UEKCLBEQSA-N
Standard InCHI:	InChI=1S/C27H38O3/c1-18(7-10-20-17-21(25(29)30)11-13-23(20)28)8-12-22-19(2)9-14-24-26(3,4)15-6-16-27(22,24)5/h7,11,13,17,24,28H,6,8-10,12,14-16H2,1-5H3,(H,29,30)/b18-7+/t24-,27+/m0/s1
SMILES:	C/C(=CCc1cc(ccc1O)C(=O)O)/CCC1=C(C)CC[C@@H]2[C@]1(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455101
PubChem CID:	11361892
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO30491	Acanthodendrilla	Genus	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620270]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1441	Individual Protein	MAP kinase-activated protein kinase 2	Homo sapiens	IC50	=	9600.0	nM	PMID[509037]

☑ 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 NPC193203 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	287
0.1-0.2	1361
0.2-0.3	2553
0.3-0.4	6720
0.4-0.5	11558
0.5-0.6	7132
0.6-0.7	9841
0.7-0.8	3031
0.8-0.85	175
0.85-0.9	27
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9918	High Similarity	NPC117899
0.9758	High Similarity	NPC18798
0.9675	High Similarity	NPC229894
0.9587	High Similarity	NPC174991
0.9375	High Similarity	NPC477594
0.9302	High Similarity	NPC477596
0.916	High Similarity	NPC477592
0.9091	High Similarity	NPC477593
0.9091	High Similarity	NPC474890
0.9091	High Similarity	NPC161943
0.9091	High Similarity	NPC273282
0.8976	High Similarity	NPC72667
0.8926	High Similarity	NPC83718
0.8898	High Similarity	NPC254492
0.8889	High Similarity	NPC477595
0.8837	High Similarity	NPC171460
0.8828	High Similarity	NPC84672
0.8828	High Similarity	NPC69424
0.8828	High Similarity	NPC78364
0.8828	High Similarity	NPC176130
0.876	High Similarity	NPC96024
0.874	High Similarity	NPC199273
0.8692	High Similarity	NPC276238
0.8633	High Similarity	NPC258856
0.8626	High Similarity	NPC108129
0.8615	High Similarity	NPC3009
0.8583	High Similarity	NPC282577
0.8583	High Similarity	NPC67300
0.8571	High Similarity	NPC241001
0.8561	High Similarity	NPC471851
0.855	High Similarity	NPC303910
0.8525	High Similarity	NPC242136
0.8516	High Similarity	NPC275145
0.8507	High Similarity	NPC475088
0.8504	High Similarity	NPC162935
0.8504	High Similarity	NPC249340
0.8504	High Similarity	NPC154696
0.85	High Similarity	NPC75295
0.8496	Intermediate Similarity	NPC175738
0.8489	Intermediate Similarity	NPC271451
0.8462	Intermediate Similarity	NPC473751
0.8456	Intermediate Similarity	NPC53001
0.845	Intermediate Similarity	NPC184219
0.8444	Intermediate Similarity	NPC290803
0.8438	Intermediate Similarity	NPC475192
0.8438	Intermediate Similarity	NPC121168
0.8433	Intermediate Similarity	NPC138472
0.8433	Intermediate Similarity	NPC477139
0.8433	Intermediate Similarity	NPC78307
0.8433	Intermediate Similarity	NPC49742
0.8425	Intermediate Similarity	NPC164852
0.8425	Intermediate Similarity	NPC259703
0.8425	Intermediate Similarity	NPC32322
0.8413	Intermediate Similarity	NPC42657
0.8406	Intermediate Similarity	NPC172311
0.84	Intermediate Similarity	NPC174087
0.8394	Intermediate Similarity	NPC87723
0.8394	Intermediate Similarity	NPC230811
0.8387	Intermediate Similarity	NPC322197
0.8385	Intermediate Similarity	NPC137416
0.8385	Intermediate Similarity	NPC123506
0.8382	Intermediate Similarity	NPC118919
0.838	Intermediate Similarity	NPC325032
0.838	Intermediate Similarity	NPC477483
0.837	Intermediate Similarity	NPC202225
0.837	Intermediate Similarity	NPC194970
0.8369	Intermediate Similarity	NPC208293
0.8333	Intermediate Similarity	NPC140133
0.8333	Intermediate Similarity	NPC473017
0.8321	Intermediate Similarity	NPC204579
0.8321	Intermediate Similarity	NPC71610
0.8321	Intermediate Similarity	NPC62952
0.8309	Intermediate Similarity	NPC249272
0.8296	Intermediate Similarity	NPC475457
0.8296	Intermediate Similarity	NPC111845
0.8296	Intermediate Similarity	NPC180261
0.8296	Intermediate Similarity	NPC475627
0.8296	Intermediate Similarity	NPC475346
0.8296	Intermediate Similarity	NPC18982
0.8296	Intermediate Similarity	NPC37299
0.8286	Intermediate Similarity	NPC477209
0.8286	Intermediate Similarity	NPC184935
0.8284	Intermediate Similarity	NPC476847
0.8281	Intermediate Similarity	NPC216216
0.8271	Intermediate Similarity	NPC25736
0.8264	Intermediate Similarity	NPC162569
0.8264	Intermediate Similarity	NPC470039
0.8264	Intermediate Similarity	NPC327962
0.8264	Intermediate Similarity	NPC179128
0.8264	Intermediate Similarity	NPC35160
0.8264	Intermediate Similarity	NPC267469
0.8264	Intermediate Similarity	NPC87630
0.8264	Intermediate Similarity	NPC116292
0.8261	Intermediate Similarity	NPC473622
0.8258	Intermediate Similarity	NPC100067
0.8258	Intermediate Similarity	NPC116513
0.8258	Intermediate Similarity	NPC103356
0.8258	Intermediate Similarity	NPC72158
0.8258	Intermediate Similarity	NPC266689
0.8258	Intermediate Similarity	NPC23126
0.8258	Intermediate Similarity	NPC169250
0.8258	Intermediate Similarity	NPC30501
0.8258	Intermediate Similarity	NPC98254
0.8258	Intermediate Similarity	NPC105157
0.8258	Intermediate Similarity	NPC190043
0.8258	Intermediate Similarity	NPC162612
0.8252	Intermediate Similarity	NPC5568
0.8248	Intermediate Similarity	NPC7464
0.8244	Intermediate Similarity	NPC137750
0.8235	Intermediate Similarity	NPC293454
0.8235	Intermediate Similarity	NPC12070
0.8235	Intermediate Similarity	NPC270899
0.8227	Intermediate Similarity	NPC100242
0.8222	Intermediate Similarity	NPC302844
0.8217	Intermediate Similarity	NPC295034
0.8209	Intermediate Similarity	NPC17840
0.8209	Intermediate Similarity	NPC247477
0.8207	Intermediate Similarity	NPC37642
0.8203	Intermediate Similarity	NPC478121
0.8197	Intermediate Similarity	NPC95172
0.8195	Intermediate Similarity	NPC221777
0.8195	Intermediate Similarity	NPC473744
0.8195	Intermediate Similarity	NPC21305
0.8194	Intermediate Similarity	NPC279442
0.8194	Intermediate Similarity	NPC17600
0.8188	Intermediate Similarity	NPC475957
0.8188	Intermediate Similarity	NPC36868
0.8188	Intermediate Similarity	NPC277559
0.8182	Intermediate Similarity	NPC29883
0.8182	Intermediate Similarity	NPC3224
0.8182	Intermediate Similarity	NPC110211
0.8182	Intermediate Similarity	NPC267846
0.8182	Intermediate Similarity	NPC15837
0.8175	Intermediate Similarity	NPC173569
0.8175	Intermediate Similarity	NPC477874
0.8175	Intermediate Similarity	NPC153088
0.8175	Intermediate Similarity	NPC283088
0.8169	Intermediate Similarity	NPC260152
0.8162	Intermediate Similarity	NPC114183
0.8162	Intermediate Similarity	NPC4170
0.8154	Intermediate Similarity	NPC309765
0.8154	Intermediate Similarity	NPC176208
0.8151	Intermediate Similarity	NPC124842
0.8148	Intermediate Similarity	NPC41847
0.8143	Intermediate Similarity	NPC471853
0.8143	Intermediate Similarity	NPC470986
0.8143	Intermediate Similarity	NPC169452
0.8143	Intermediate Similarity	NPC315578
0.8143	Intermediate Similarity	NPC181560
0.8143	Intermediate Similarity	NPC168471
0.8138	Intermediate Similarity	NPC142654
0.8138	Intermediate Similarity	NPC247219
0.8138	Intermediate Similarity	NPC52931
0.8134	Intermediate Similarity	NPC99731
0.8134	Intermediate Similarity	NPC131684
0.8134	Intermediate Similarity	NPC474998
0.8134	Intermediate Similarity	NPC194979
0.813	Intermediate Similarity	NPC116842
0.8129	Intermediate Similarity	NPC149773
0.8129	Intermediate Similarity	NPC245760
0.8129	Intermediate Similarity	NPC46242
0.8129	Intermediate Similarity	NPC91887
0.8129	Intermediate Similarity	NPC28592
0.8129	Intermediate Similarity	NPC297797
0.8129	Intermediate Similarity	NPC114333
0.8129	Intermediate Similarity	NPC51531
0.8129	Intermediate Similarity	NPC4214
0.8129	Intermediate Similarity	NPC157284
0.8129	Intermediate Similarity	NPC165191
0.8129	Intermediate Similarity	NPC473779
0.8129	Intermediate Similarity	NPC5014
0.8129	Intermediate Similarity	NPC289358
0.8129	Intermediate Similarity	NPC50615
0.8129	Intermediate Similarity	NPC469857
0.8129	Intermediate Similarity	NPC477849
0.8129	Intermediate Similarity	NPC23667
0.8129	Intermediate Similarity	NPC473479
0.8129	Intermediate Similarity	NPC42384
0.8125	Intermediate Similarity	NPC473767
0.812	Intermediate Similarity	NPC121104
0.812	Intermediate Similarity	NPC209959
0.8116	Intermediate Similarity	NPC471670
0.8116	Intermediate Similarity	NPC472308
0.8116	Intermediate Similarity	NPC191976
0.8116	Intermediate Similarity	NPC249817
0.8112	Intermediate Similarity	NPC97188
0.811	Intermediate Similarity	NPC160199
0.8106	Intermediate Similarity	NPC49938
0.8106	Intermediate Similarity	NPC87985
0.8102	Intermediate Similarity	NPC282780
0.8102	Intermediate Similarity	NPC50924
0.8102	Intermediate Similarity	NPC213122
0.8102	Intermediate Similarity	NPC166480
0.8099	Intermediate Similarity	NPC184658
0.8092	Intermediate Similarity	NPC472029
0.8092	Intermediate Similarity	NPC273683
0.8092	Intermediate Similarity	NPC65761
0.8088	Intermediate Similarity	NPC165612
0.8088	Intermediate Similarity	NPC58685
0.8077	Intermediate Similarity	NPC120545

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 NPC193203 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	894
0.2-0.3	1216
0.3-0.4	2433
0.4-0.5	2487
0.5-0.6	1250
0.6-0.7	499
0.7-0.8	84
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8413	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD7003	Approved
0.8062	Intermediate Similarity	NPD2932	Approved
0.8058	Intermediate Similarity	NPD5406	Approved
0.8058	Intermediate Similarity	NPD5405	Approved
0.8058	Intermediate Similarity	NPD5404	Approved
0.8058	Intermediate Similarity	NPD5408	Approved
0.8016	Intermediate Similarity	NPD5951	Approved
0.797	Intermediate Similarity	NPD1164	Approved
0.7939	Intermediate Similarity	NPD1201	Approved
0.7923	Intermediate Similarity	NPD3019	Approved
0.7907	Intermediate Similarity	NPD9545	Approved
0.7891	Intermediate Similarity	NPD7458	Discontinued
0.7887	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1470	Approved
0.781	Intermediate Similarity	NPD3764	Approved
0.7786	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD6663	Approved
0.7721	Intermediate Similarity	NPD5736	Approved
0.7708	Intermediate Similarity	NPD4628	Phase 3
0.7708	Intermediate Similarity	NPD8166	Discontinued
0.7612	Intermediate Similarity	NPD3972	Approved
0.7606	Intermediate Similarity	NPD2799	Discontinued
0.7586	Intermediate Similarity	NPD3750	Approved
0.7586	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD2935	Discontinued
0.7551	Intermediate Similarity	NPD7390	Discontinued
0.754	Intermediate Similarity	NPD9266	Approved
0.754	Intermediate Similarity	NPD74	Approved
0.7481	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD9493	Approved
0.7465	Intermediate Similarity	NPD1607	Approved
0.746	Intermediate Similarity	NPD9263	Approved
0.746	Intermediate Similarity	NPD9267	Approved
0.746	Intermediate Similarity	NPD9264	Approved
0.7451	Intermediate Similarity	NPD7819	Suspended
0.7447	Intermediate Similarity	NPD1240	Approved
0.7445	Intermediate Similarity	NPD2797	Approved
0.7419	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1930	Approved
0.7419	Intermediate Similarity	NPD1929	Approved
0.7403	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2798	Approved
0.7372	Intermediate Similarity	NPD1283	Approved
0.7355	Intermediate Similarity	NPD1809	Phase 2
0.7343	Intermediate Similarity	NPD6651	Approved
0.7333	Intermediate Similarity	NPD3023	Approved
0.7333	Intermediate Similarity	NPD6273	Approved
0.7333	Intermediate Similarity	NPD3026	Approved
0.7329	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD943	Approved
0.732	Intermediate Similarity	NPD7411	Suspended
0.7317	Intermediate Similarity	NPD3020	Approved
0.7317	Intermediate Similarity	NPD2066	Phase 3
0.7313	Intermediate Similarity	NPD3025	Approved
0.7313	Intermediate Similarity	NPD3024	Approved
0.7312	Intermediate Similarity	NPD7473	Discontinued
0.731	Intermediate Similarity	NPD6099	Approved
0.731	Intermediate Similarity	NPD6100	Approved
0.7308	Intermediate Similarity	NPD7075	Discontinued
0.7305	Intermediate Similarity	NPD3268	Approved
0.7303	Intermediate Similarity	NPD3226	Approved
0.7267	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2346	Discontinued
0.7259	Intermediate Similarity	NPD4626	Approved
0.7255	Intermediate Similarity	NPD6599	Discontinued
0.7248	Intermediate Similarity	NPD3300	Phase 2
0.7244	Intermediate Similarity	NPD7768	Phase 2
0.7241	Intermediate Similarity	NPD1510	Phase 2
0.7241	Intermediate Similarity	NPD3748	Approved
0.7234	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7008	Discontinued
0.7233	Intermediate Similarity	NPD6232	Discontinued
0.7226	Intermediate Similarity	NPD1608	Approved
0.7226	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD2859	Approved
0.7213	Intermediate Similarity	NPD2860	Approved
0.719	Intermediate Similarity	NPD845	Approved
0.7183	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD2313	Discontinued
0.7179	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7635	Approved
0.7153	Intermediate Similarity	NPD1281	Approved
0.7152	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD2532	Approved
0.7152	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD9261	Approved
0.7143	Intermediate Similarity	NPD2344	Approved
0.7143	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD8032	Phase 2
0.7133	Intermediate Similarity	NPD7236	Approved
0.7132	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD2933	Approved
0.7131	Intermediate Similarity	NPD2934	Approved
0.7131	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4308	Phase 3
0.7123	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3091	Approved
0.7101	Intermediate Similarity	NPD9269	Phase 2
0.7101	Intermediate Similarity	NPD4878	Approved
0.7095	Intermediate Similarity	NPD1549	Phase 2
0.7078	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4750	Phase 3
0.7071	Intermediate Similarity	NPD1203	Approved
0.7068	Intermediate Similarity	NPD9281	Approved
0.7063	Intermediate Similarity	NPD846	Approved
0.7063	Intermediate Similarity	NPD940	Approved
0.7059	Intermediate Similarity	NPD9268	Approved
0.7051	Intermediate Similarity	NPD6801	Discontinued
0.7047	Intermediate Similarity	NPD2800	Approved
0.7039	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4380	Phase 2
0.7029	Intermediate Similarity	NPD3092	Approved
0.7027	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD3495	Discontinued
0.7015	Intermediate Similarity	NPD256	Approved
0.7015	Intermediate Similarity	NPD255	Approved
0.7012	Intermediate Similarity	NPD5844	Phase 1
0.7007	Intermediate Similarity	NPD17	Approved
0.7007	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4059	Approved
0.7	Intermediate Similarity	NPD1876	Approved
0.6981	Remote Similarity	NPD3749	Approved
0.6978	Remote Similarity	NPD9717	Approved
0.6974	Remote Similarity	NPD6799	Approved
0.6972	Remote Similarity	NPD4208	Discontinued
0.697	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1088	Approved
0.6959	Remote Similarity	NPD2796	Approved
0.6959	Remote Similarity	NPD4477	Approved
0.6959	Remote Similarity	NPD4476	Approved
0.6954	Remote Similarity	NPD2309	Approved
0.6953	Remote Similarity	NPD5909	Discontinued
0.695	Remote Similarity	NPD3266	Approved
0.695	Remote Similarity	NPD3267	Approved
0.6942	Remote Similarity	NPD9256	Approved
0.6942	Remote Similarity	NPD9258	Approved
0.694	Remote Similarity	NPD2629	Approved
0.6934	Remote Similarity	NPD5691	Approved
0.6929	Remote Similarity	NPD1755	Approved
0.6923	Remote Similarity	NPD2342	Discontinued
0.6923	Remote Similarity	NPD6832	Phase 2
0.6918	Remote Similarity	NPD230	Phase 1
0.6918	Remote Similarity	NPD6355	Discontinued
0.6912	Remote Similarity	NPD7610	Discontinued
0.6911	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6020	Phase 2
0.6903	Remote Similarity	NPD7239	Suspended
0.6899	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3400	Discontinued
0.6882	Remote Similarity	NPD8150	Discontinued
0.688	Remote Similarity	NPD288	Approved
0.6866	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD8127	Discontinued
0.685	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4060	Phase 1
0.6849	Remote Similarity	NPD4307	Phase 2
0.6849	Remote Similarity	NPD2979	Phase 3
0.6848	Remote Similarity	NPD7177	Discontinued
0.6846	Remote Similarity	NPD1551	Phase 2
0.6842	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3094	Phase 2
0.6828	Remote Similarity	NPD6798	Discontinued
0.6822	Remote Similarity	NPD1237	Approved
0.6821	Remote Similarity	NPD1243	Approved
0.6818	Remote Similarity	NPD3022	Approved
0.6818	Remote Similarity	NPD3021	Approved
0.6813	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1651	Approved
0.6806	Remote Similarity	NPD4207	Discontinued
0.6803	Remote Similarity	NPD1090	Approved
0.6803	Remote Similarity	NPD1089	Approved
0.6803	Remote Similarity	NPD1086	Approved
0.6802	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.68	Remote Similarity	NPD844	Approved
0.6797	Remote Similarity	NPD1932	Approved
0.6786	Remote Similarity	NPD422	Phase 1
0.6784	Remote Similarity	NPD8434	Phase 2
0.6779	Remote Similarity	NPD7033	Discontinued
0.6776	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5049	Phase 3
0.6774	Remote Similarity	NPD1202	Approved
0.6767	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4589	Approved
0.6763	Remote Similarity	NPD1778	Approved
0.6763	Remote Similarity	NPD3095	Discontinued
0.6761	Remote Similarity	NPD3225	Approved
0.6759	Remote Similarity	NPD7095	Approved
0.675	Remote Similarity	NPD4288	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