NPASS Compound

Structure

NPC474890 OpenBabel07101719512D 25 25 0 0 0 0 0 0 0 0999 V2000 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -1.7321 -0.0000 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 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 -5.1962 -3.0000 0.0000 C 0 0 0 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 -2.5981 -1.5000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 17 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 18 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 20 2 0 0 0 0 14 21 2 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 22 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.22
Volume:	388.427
LogP:	5.423
LogD:	4.459
LogS:	-3.829
# Rotatable Bonds:	9
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.537
Synthetic Accessibility Score:	2.689
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.836
MDCK Permeability:	1.4434933291340712e-05
Pgp-inhibitor:	0.086
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.162
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	100.06658172607422%
Volume Distribution (VD):	0.621
Pgp-substrate:	0.43641602993011475%

ADMET: Metabolism

CYP1A2-inhibitor:	0.332
CYP1A2-substrate:	0.562
CYP2C19-inhibitor:	0.106
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.582
CYP2C9-substrate:	0.729
CYP2D6-inhibitor:	0.661
CYP2D6-substrate:	0.276
CYP3A4-inhibitor:	0.075
CYP3A4-substrate:	0.101

ADMET: Excretion

Clearance (CL):	5.268
Half-life (T1/2):	0.957

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.84
Drug-inuced Liver Injury (DILI):	0.176
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.532
Carcinogencity:	0.079
Eye Corrosion:	0.004
Eye Irritation:	0.542
Respiratory Toxicity:	0.018

Download Data

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

Natural Product: NPC474890

Natural Product ID:	NPC474890
*Common Name:**	3-Farnesyl-4-Hydroxybenzoic Acid
IUPAC Name:	4-hydroxy-3-[(2Z,6Z)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzoic acid
Synonyms:
Standard InCHIKey:	QUYGEGSOVYMIEU-YYIZJUOFSA-N
Standard InCHI:	InChI=1S/C22H30O3/c1-16(2)7-5-8-17(3)9-6-10-18(4)11-12-19-15-20(22(24)25)13-14-21(19)23/h7,9,11,13-15,23H,5-6,8,10,12H2,1-4H3,(H,24,25)/b17-9-,18-11-
SMILES:	C/C(=C/Cc1cc(ccc1O)C(=O)O)/CC/C=C(CCC=C(C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486272
PubChem CID:	44559229
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
NPO9458	Limnophila geoffrayi	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038568]

☑ 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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT935	Individual Protein	Quinone reductase 1)	Homo sapiens	CD	>	20.0	ug ml-1	PMID[491672]

☑ 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 NPC474890 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	253
0.1-0.2	1367
0.2-0.3	3406
0.3-0.4	9518
0.4-0.5	10082
0.5-0.6	5893
0.6-0.7	8845
0.7-0.8	3026
0.8-0.85	225
0.85-0.9	69
0.9-0.95	6
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC273282
1.0	High Similarity	NPC161943
0.9818	High Similarity	NPC83718
0.9483	High Similarity	NPC174991
0.9397	High Similarity	NPC67300
0.9369	High Similarity	NPC242136
0.9244	High Similarity	NPC473751
0.9237	High Similarity	NPC184219
0.9231	High Similarity	NPC475192
0.9091	High Similarity	NPC229894
0.9091	High Similarity	NPC193203
0.9016	High Similarity	NPC117899
0.9009	High Similarity	NPC95172
0.9	High Similarity	NPC29883
0.8934	High Similarity	NPC473744
0.8909	High Similarity	NPC184658
0.8908	High Similarity	NPC309765
0.8889	High Similarity	NPC473767
0.8871	High Similarity	NPC18798
0.8852	High Similarity	NPC121104
0.8829	High Similarity	NPC226699
0.8824	High Similarity	NPC303737
0.8818	High Similarity	NPC303141
0.8818	High Similarity	NPC243677
0.88	High Similarity	NPC302844
0.8793	High Similarity	NPC131192
0.877	High Similarity	NPC62952
0.875	High Similarity	NPC91105
0.8739	High Similarity	NPC6984
0.872	High Similarity	NPC473777
0.8718	High Similarity	NPC174087
0.8699	High Similarity	NPC98254
0.8699	High Similarity	NPC23126
0.8699	High Similarity	NPC72158
0.8699	High Similarity	NPC30501
0.8699	High Similarity	NPC190043
0.8699	High Similarity	NPC162612
0.8699	High Similarity	NPC105157
0.8699	High Similarity	NPC100067
0.8699	High Similarity	NPC266689
0.8699	High Similarity	NPC169250
0.8699	High Similarity	NPC103356
0.8696	High Similarity	NPC211421
0.8678	High Similarity	NPC65761
0.8678	High Similarity	NPC472029
0.8667	High Similarity	NPC215392
0.8661	High Similarity	NPC477594
0.8644	High Similarity	NPC27633
0.8644	High Similarity	NPC94298
0.864	High Similarity	NPC327457
0.864	High Similarity	NPC86774
0.8636	High Similarity	NPC470202
0.8629	High Similarity	NPC473017
0.8629	High Similarity	NPC21305
0.8629	High Similarity	NPC221777
0.8618	High Similarity	NPC204579
0.8618	High Similarity	NPC110211
0.8618	High Similarity	NPC267846
0.8596	High Similarity	NPC116842
0.8594	High Similarity	NPC477596
0.8584	High Similarity	NPC470039
0.8583	High Similarity	NPC216216
0.8583	High Similarity	NPC149246
0.8571	High Similarity	NPC161617
0.856	High Similarity	NPC474998
0.8559	High Similarity	NPC160199
0.8548	High Similarity	NPC116513
0.8547	High Similarity	NPC322197
0.8537	High Similarity	NPC49938
0.8537	High Similarity	NPC475733
0.8516	High Similarity	NPC204582
0.8512	High Similarity	NPC295034
0.8509	High Similarity	NPC75272
0.8509	High Similarity	NPC471954
0.85	High Similarity	NPC159525
0.8496	Intermediate Similarity	NPC228737
0.8492	Intermediate Similarity	NPC247477
0.8492	Intermediate Similarity	NPC17840
0.8492	Intermediate Similarity	NPC109778
0.8487	Intermediate Similarity	NPC241089
0.848	Intermediate Similarity	NPC2401
0.8462	Intermediate Similarity	NPC477592
0.8455	Intermediate Similarity	NPC52472
0.8443	Intermediate Similarity	NPC282577
0.8443	Intermediate Similarity	NPC297193
0.8438	Intermediate Similarity	NPC239855
0.8438	Intermediate Similarity	NPC37299
0.8438	Intermediate Similarity	NPC180261
0.843	Intermediate Similarity	NPC190971
0.8425	Intermediate Similarity	NPC475042
0.8421	Intermediate Similarity	NPC17525
0.8421	Intermediate Similarity	NPC224584
0.8417	Intermediate Similarity	NPC158222
0.8417	Intermediate Similarity	NPC61779
0.8413	Intermediate Similarity	NPC194979
0.8407	Intermediate Similarity	NPC317592
0.8403	Intermediate Similarity	NPC121259
0.84	Intermediate Similarity	NPC209959
0.8397	Intermediate Similarity	NPC477593
0.8385	Intermediate Similarity	NPC118919
0.8376	Intermediate Similarity	NPC11824
0.8374	Intermediate Similarity	NPC275145
0.8364	Intermediate Similarity	NPC245561
0.8362	Intermediate Similarity	NPC114682
0.8362	Intermediate Similarity	NPC212718
0.8361	Intermediate Similarity	NPC226275
0.8361	Intermediate Similarity	NPC156139
0.8347	Intermediate Similarity	NPC294037
0.8333	Intermediate Similarity	NPC19622
0.8333	Intermediate Similarity	NPC141523
0.8333	Intermediate Similarity	NPC40649
0.8333	Intermediate Similarity	NPC112789
0.8333	Intermediate Similarity	NPC249435
0.8333	Intermediate Similarity	NPC96024
0.8333	Intermediate Similarity	NPC209486
0.8333	Intermediate Similarity	NPC2596
0.8333	Intermediate Similarity	NPC184527
0.832	Intermediate Similarity	NPC95309
0.832	Intermediate Similarity	NPC254492
0.8308	Intermediate Similarity	NPC470210
0.8308	Intermediate Similarity	NPC290803
0.8306	Intermediate Similarity	NPC199273
0.8306	Intermediate Similarity	NPC221798
0.8305	Intermediate Similarity	NPC114918
0.8304	Intermediate Similarity	NPC13426
0.8295	Intermediate Similarity	NPC139074
0.8295	Intermediate Similarity	NPC213485
0.8295	Intermediate Similarity	NPC40524
0.8293	Intermediate Similarity	NPC68167
0.8293	Intermediate Similarity	NPC133909
0.8293	Intermediate Similarity	NPC32032
0.8291	Intermediate Similarity	NPC231717
0.8279	Intermediate Similarity	NPC146642
0.8279	Intermediate Similarity	NPC35856
0.8279	Intermediate Similarity	NPC301987
0.8279	Intermediate Similarity	NPC292665
0.8279	Intermediate Similarity	NPC178395
0.8279	Intermediate Similarity	NPC115188
0.8279	Intermediate Similarity	NPC26433
0.8279	Intermediate Similarity	NPC297186
0.8279	Intermediate Similarity	NPC159760
0.8279	Intermediate Similarity	NPC165197
0.8279	Intermediate Similarity	NPC179092
0.8279	Intermediate Similarity	NPC244994
0.8279	Intermediate Similarity	NPC222876
0.8279	Intermediate Similarity	NPC272454
0.8271	Intermediate Similarity	NPC275903
0.8271	Intermediate Similarity	NPC469911
0.8268	Intermediate Similarity	NPC476119
0.8264	Intermediate Similarity	NPC233165
0.8264	Intermediate Similarity	NPC184579
0.8261	Intermediate Similarity	NPC100551
0.8261	Intermediate Similarity	NPC31274
0.8254	Intermediate Similarity	NPC37512
0.8254	Intermediate Similarity	NPC72667
0.8254	Intermediate Similarity	NPC176130
0.8254	Intermediate Similarity	NPC78364
0.8254	Intermediate Similarity	NPC84672
0.8254	Intermediate Similarity	NPC69424
0.8246	Intermediate Similarity	NPC95178
0.8246	Intermediate Similarity	NPC29989
0.8246	Intermediate Similarity	NPC69332
0.8244	Intermediate Similarity	NPC474726
0.8244	Intermediate Similarity	NPC475955
0.8244	Intermediate Similarity	NPC475111
0.824	Intermediate Similarity	NPC201728
0.824	Intermediate Similarity	NPC123506
0.824	Intermediate Similarity	NPC477454
0.824	Intermediate Similarity	NPC262671
0.8231	Intermediate Similarity	NPC282780
0.8231	Intermediate Similarity	NPC27643
0.8231	Intermediate Similarity	NPC166480
0.8226	Intermediate Similarity	NPC477153
0.8211	Intermediate Similarity	NPC242895
0.8211	Intermediate Similarity	NPC115159
0.8211	Intermediate Similarity	NPC143427
0.8211	Intermediate Similarity	NPC45438
0.8211	Intermediate Similarity	NPC25168
0.8211	Intermediate Similarity	NPC224273
0.8211	Intermediate Similarity	NPC19174
0.8211	Intermediate Similarity	NPC196976
0.8211	Intermediate Similarity	NPC73532
0.8211	Intermediate Similarity	NPC267552
0.8209	Intermediate Similarity	NPC477595
0.8205	Intermediate Similarity	NPC268388
0.8205	Intermediate Similarity	NPC228609
0.8203	Intermediate Similarity	NPC163169
0.8203	Intermediate Similarity	NPC470987
0.8203	Intermediate Similarity	NPC245395
0.8203	Intermediate Similarity	NPC21378
0.8203	Intermediate Similarity	NPC123
0.8198	Intermediate Similarity	NPC280869
0.8195	Intermediate Similarity	NPC473988
0.819	Intermediate Similarity	NPC88141
0.8189	Intermediate Similarity	NPC3009
0.8182	Intermediate Similarity	NPC194579
0.8175	Intermediate Similarity	NPC473691
0.8174	Intermediate Similarity	NPC34715
0.8168	Intermediate Similarity	NPC70859
0.8168	Intermediate Similarity	NPC283590

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 NPC474890 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	909
0.2-0.3	1437
0.3-0.4	2586
0.4-0.5	2184
0.5-0.6	1211
0.6-0.7	463
0.7-0.8	91
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD9265	Clinical (unspecified phase)
0.8729	High Similarity	NPD4196	Clinical (unspecified phase)
0.8644	High Similarity	NPD9545	Approved
0.8261	Intermediate Similarity	NPD9266	Approved
0.8261	Intermediate Similarity	NPD74	Approved
0.824	Intermediate Similarity	NPD1164	Approved
0.8174	Intermediate Similarity	NPD9267	Approved
0.8174	Intermediate Similarity	NPD9264	Approved
0.8174	Intermediate Similarity	NPD9263	Approved
0.8167	Intermediate Similarity	NPD9493	Approved
0.8134	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD5404	Approved
0.791	Intermediate Similarity	NPD2935	Discontinued
0.791	Intermediate Similarity	NPD5405	Approved
0.791	Intermediate Similarity	NPD5406	Approved
0.791	Intermediate Similarity	NPD5408	Approved
0.7826	Intermediate Similarity	NPD9261	Approved
0.7803	Intermediate Similarity	NPD1240	Approved
0.7786	Intermediate Similarity	NPD3764	Approved
0.7778	Intermediate Similarity	NPD1201	Approved
0.7739	Intermediate Similarity	NPD846	Approved
0.7739	Intermediate Similarity	NPD940	Approved
0.7717	Intermediate Similarity	NPD9269	Phase 2
0.7705	Intermediate Similarity	NPD9281	Approved
0.7704	Intermediate Similarity	NPD2799	Discontinued
0.7704	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1607	Approved
0.768	Intermediate Similarity	NPD9268	Approved
0.7674	Intermediate Similarity	NPD1470	Approved
0.7669	Intermediate Similarity	NPD943	Approved
0.7642	Intermediate Similarity	NPD255	Approved
0.7642	Intermediate Similarity	NPD256	Approved
0.7636	Intermediate Similarity	NPD9258	Approved
0.7636	Intermediate Similarity	NPD9256	Approved
0.7611	Intermediate Similarity	NPD2859	Approved
0.7611	Intermediate Similarity	NPD2860	Approved
0.7611	Intermediate Similarity	NPD1809	Phase 2
0.7589	Intermediate Similarity	NPD845	Approved
0.7581	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD9717	Approved
0.7561	Intermediate Similarity	NPD5951	Approved
0.7554	Intermediate Similarity	NPD4628	Phase 3
0.7554	Intermediate Similarity	NPD7003	Approved
0.7522	Intermediate Similarity	NPD2933	Approved
0.7522	Intermediate Similarity	NPD2934	Approved
0.7521	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD1930	Approved
0.7521	Intermediate Similarity	NPD1929	Approved
0.7517	Intermediate Similarity	NPD7411	Suspended
0.7481	Intermediate Similarity	NPD230	Phase 1
0.748	Intermediate Similarity	NPD4626	Approved
0.7465	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD1510	Phase 2
0.7442	Intermediate Similarity	NPD3972	Approved
0.7429	Intermediate Similarity	NPD3750	Approved
0.7414	Intermediate Similarity	NPD3020	Approved
0.741	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2797	Approved
0.7405	Intermediate Similarity	NPD1203	Approved
0.7394	Intermediate Similarity	NPD7390	Discontinued
0.7388	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD2313	Discontinued
0.7383	Intermediate Similarity	NPD7075	Discontinued
0.7379	Intermediate Similarity	NPD7458	Discontinued
0.7368	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD2798	Approved
0.7344	Intermediate Similarity	NPD3019	Approved
0.7344	Intermediate Similarity	NPD2932	Approved
0.7343	Intermediate Similarity	NPD2534	Approved
0.7343	Intermediate Similarity	NPD2532	Approved
0.7343	Intermediate Similarity	NPD2533	Approved
0.7338	Intermediate Similarity	NPD2344	Approved
0.7323	Intermediate Similarity	NPD1759	Phase 1
0.7319	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1608	Approved
0.7304	Intermediate Similarity	NPD844	Approved
0.7302	Intermediate Similarity	NPD9568	Approved
0.7297	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7819	Suspended
0.7286	Intermediate Similarity	NPD1549	Phase 2
0.7273	Intermediate Similarity	NPD9259	Approved
0.7273	Intermediate Similarity	NPD6799	Approved
0.7273	Intermediate Similarity	NPD9257	Approved
0.7265	Intermediate Similarity	NPD2066	Phase 3
0.7259	Intermediate Similarity	NPD3268	Approved
0.7244	Intermediate Similarity	NPD1758	Phase 1
0.7234	Intermediate Similarity	NPD1243	Approved
0.7231	Intermediate Similarity	NPD422	Phase 1
0.723	Intermediate Similarity	NPD6801	Discontinued
0.7218	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4380	Phase 2
0.7209	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7768	Phase 2
0.7197	Intermediate Similarity	NPD1283	Approved
0.7194	Intermediate Similarity	NPD4308	Phase 3
0.7183	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD111	Approved
0.7174	Intermediate Similarity	NPD6651	Approved
0.7167	Intermediate Similarity	NPD1237	Approved
0.7164	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD2796	Approved
0.7143	Intermediate Similarity	NPD3226	Approved
0.7133	Intermediate Similarity	NPD2309	Approved
0.7132	Intermediate Similarity	NPD5691	Approved
0.713	Intermediate Similarity	NPD1202	Approved
0.712	Intermediate Similarity	NPD5277	Phase 2
0.7111	Intermediate Similarity	NPD6832	Phase 2
0.7097	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6599	Discontinued
0.7094	Intermediate Similarity	NPD288	Approved
0.7092	Intermediate Similarity	NPD2346	Discontinued
0.7092	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6663	Approved
0.708	Intermediate Similarity	NPD520	Approved
0.708	Intermediate Similarity	NPD800	Approved
0.7078	Intermediate Similarity	NPD6232	Discontinued
0.7077	Intermediate Similarity	NPD17	Approved
0.7071	Intermediate Similarity	NPD3748	Approved
0.7067	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1241	Discontinued
0.7063	Intermediate Similarity	NPD3400	Discontinued
0.7063	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5049	Phase 3
0.7049	Intermediate Similarity	NPD3134	Approved
0.7045	Intermediate Similarity	NPD1481	Phase 2
0.704	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4208	Discontinued
0.7037	Intermediate Similarity	NPD5736	Approved
0.7034	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD9495	Approved
0.7023	Intermediate Similarity	NPD3847	Discontinued
0.7021	Intermediate Similarity	NPD4476	Approved
0.7021	Intermediate Similarity	NPD4477	Approved
0.7021	Intermediate Similarity	NPD1551	Phase 2
0.702	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1090	Approved
0.7018	Intermediate Similarity	NPD1086	Approved
0.7018	Intermediate Similarity	NPD1089	Approved
0.7016	Intermediate Similarity	NPD4750	Phase 3
0.7014	Intermediate Similarity	NPD2354	Approved
0.7007	Intermediate Similarity	NPD6798	Discontinued
0.7007	Intermediate Similarity	NPD411	Approved
0.7	Intermediate Similarity	NPD9491	Approved
0.6993	Remote Similarity	NPD2800	Approved
0.6992	Remote Similarity	NPD1755	Approved
0.6986	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4207	Discontinued
0.6983	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD447	Suspended
0.6974	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1535	Discovery
0.697	Remote Similarity	NPD1281	Approved
0.6966	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD258	Approved
0.6963	Remote Similarity	NPD257	Approved
0.695	Remote Similarity	NPD7033	Discontinued
0.6947	Remote Similarity	NPD1778	Approved
0.6944	Remote Similarity	NPD8166	Discontinued
0.6943	Remote Similarity	NPD7473	Discontinued
0.694	Remote Similarity	NPD1876	Approved
0.694	Remote Similarity	NPD3225	Approved
0.6939	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2182	Approved
0.6929	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3749	Approved
0.6923	Remote Similarity	NPD1693	Approved
0.6923	Remote Similarity	NPD1894	Discontinued
0.6906	Remote Similarity	NPD4307	Phase 2
0.6897	Remote Similarity	NPD6190	Approved
0.6897	Remote Similarity	NPD1088	Approved
0.6892	Remote Similarity	NPD920	Approved
0.6889	Remote Similarity	NPD3267	Approved
0.6889	Remote Similarity	NPD3266	Approved
0.6885	Remote Similarity	NPD5909	Discontinued
0.6885	Remote Similarity	NPD164	Approved
0.688	Remote Similarity	NPD3022	Approved
0.688	Remote Similarity	NPD3021	Approved
0.6875	Remote Similarity	NPD2629	Approved
0.6875	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5953	Discontinued
0.6871	Remote Similarity	NPD642	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1932	Approved
0.6857	Remote Similarity	NPD6355	Discontinued
0.6855	Remote Similarity	NPD7286	Phase 2
0.6855	Remote Similarity	NPD5844	Phase 1
0.6855	Remote Similarity	NPD1358	Approved
0.6853	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6005	Phase 3
0.6853	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2353	Approved
0.6853	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6004	Phase 3
0.6853	Remote Similarity	NPD6002	Phase 3
0.685	Remote Similarity	NPD7635	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