NPASS Compound

Structure

CID115188 OpenBabel06191715472D 25 25 0 0 0 0 0 0 0 0999 V2000 -12.1244 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 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 -5.1962 -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 -3.4641 -1.0000 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 -1.7321 -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 -0.8660 -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 1.7321 -0.0000 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 0.8660 0.5000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 19 1 0 0 0 0 18 20 2 0 0 0 0 19 21 2 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 21 22 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.24
Volume:	391.064
LogP:	6.699
LogD:	4.925
LogS:	-2.993
# Rotatable Bonds:	13
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	2.548
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.127
MDCK Permeability:	2.7080386644229293e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	100.66532135009766%
Volume Distribution (VD):	0.295
Pgp-substrate:	0.4844304621219635%

ADMET: Metabolism

CYP1A2-inhibitor:	0.399
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.356
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.517
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.857
CYP2D6-substrate:	0.301
CYP3A4-inhibitor:	0.172
CYP3A4-substrate:	0.024

ADMET: Excretion

Clearance (CL):	1.663
Half-life (T1/2):	0.803

ADMET: Toxicity

hERG Blockers:	0.165
Human Hepatotoxicity (H-HT):	0.748
Drug-inuced Liver Injury (DILI):	0.206
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.364
Skin Sensitization:	0.922
Carcinogencity:	0.034
Eye Corrosion:	0.021
Eye Irritation:	0.961
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC115188

Natural Product ID:	NPC115188
*Common Name:**	(8E,11E)-Anacardic Acid
IUPAC Name:	2-hydroxy-6-[(8E,11E)-pentadeca-8,11-dienyl]benzoic acid
Synonyms:	(8E,11E)-Anacardic Acid
Standard InCHIKey:	KAOMOVYHGLSFHQ-AOSYACOCSA-N
Standard InCHI:	InChI=1S/C22H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h4-5,7-8,15,17-18,23H,2-3,6,9-14,16H2,1H3,(H,24,25)/b5-4+,8-7+
SMILES:	CCC/C=C/C/C=C/CCCCCCCc1cccc(c1C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465536
PubChem CID:	9833719
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0000487] Salicylic acid and derivatives [CHEMONTID:0002514] Salicylic acids

*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
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO998	Justicia hayatai	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13016	Viscaria viscosa	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11636	Ideopsis similis	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12510	Aronia arbutifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13070	Clibadium mexiae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1744	Discaria serratifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9180	Pyrostegia venusta	Species	Bignoniaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1489	Individual Protein	Glyceraldehyde-3-phosphate dehydrogenase, glycosomal	Trypanosoma cruzi	IC50	=	69000.0	nM	PMID[456642]

☑ 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 NPC115188 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	259
0.1-0.2	1373
0.2-0.3	3401
0.3-0.4	9461
0.4-0.5	10026
0.5-0.6	6039
0.6-0.7	9315
0.7-0.8	2456
0.8-0.85	263
0.85-0.9	74
0.9-0.95	7
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC292665
1.0	High Similarity	NPC178395
1.0	High Similarity	NPC159760
1.0	High Similarity	NPC244994
1.0	High Similarity	NPC26433
1.0	High Similarity	NPC272454
1.0	High Similarity	NPC179092
1.0	High Similarity	NPC35856
1.0	High Similarity	NPC301987
1.0	High Similarity	NPC222876
0.9823	High Similarity	NPC233165
0.9823	High Similarity	NPC184579
0.9655	High Similarity	NPC244351
0.9646	High Similarity	NPC125252
0.9576	High Similarity	NPC167055
0.9576	High Similarity	NPC240744
0.9386	High Similarity	NPC477453
0.9187	High Similarity	NPC17840
0.9187	High Similarity	NPC247477
0.916	High Similarity	NPC283514
0.9076	High Similarity	NPC198336
0.9008	High Similarity	NPC91475
0.9008	High Similarity	NPC265910
0.896	High Similarity	NPC7012
0.8889	High Similarity	NPC470160
0.8862	High Similarity	NPC473691
0.8852	High Similarity	NPC470162
0.8852	High Similarity	NPC236189
0.8852	High Similarity	NPC470163
0.8833	High Similarity	NPC165197
0.8819	High Similarity	NPC37299
0.8819	High Similarity	NPC180261
0.8793	High Similarity	NPC211421
0.879	High Similarity	NPC209959
0.879	High Similarity	NPC181715
0.878	High Similarity	NPC262671
0.878	High Similarity	NPC201728
0.878	High Similarity	NPC477454
0.877	High Similarity	NPC477153
0.876	High Similarity	NPC25168
0.873	High Similarity	NPC259942
0.872	High Similarity	NPC95537
0.8692	High Similarity	NPC71256
0.8689	High Similarity	NPC297193
0.8684	High Similarity	NPC100551
0.8672	High Similarity	NPC43627
0.8655	High Similarity	NPC160199
0.8655	High Similarity	NPC121259
0.8655	High Similarity	NPC269414
0.8651	High Similarity	NPC92624
0.8644	High Similarity	NPC161304
0.8618	High Similarity	NPC275145
0.8615	High Similarity	NPC118919
0.8605	High Similarity	NPC474097
0.8595	High Similarity	NPC206778
0.8595	High Similarity	NPC285829
0.8583	High Similarity	NPC31539
0.8571	High Similarity	NPC108288
0.8571	High Similarity	NPC41263
0.8571	High Similarity	NPC312800
0.8571	High Similarity	NPC128825
0.856	High Similarity	NPC136342
0.856	High Similarity	NPC160499
0.856	High Similarity	NPC49647
0.856	High Similarity	NPC295202
0.856	High Similarity	NPC306765
0.856	High Similarity	NPC227741
0.855	High Similarity	NPC194579
0.8548	High Similarity	NPC117794
0.8538	High Similarity	NPC290803
0.8538	High Similarity	NPC142027
0.8538	High Similarity	NPC27407
0.8537	High Similarity	NPC307174
0.8522	High Similarity	NPC224584
0.8516	High Similarity	NPC214702
0.8516	High Similarity	NPC470831
0.8512	High Similarity	NPC328459
0.8512	High Similarity	NPC90522
0.8504	High Similarity	NPC474546
0.8487	Intermediate Similarity	NPC240163
0.848	Intermediate Similarity	NPC472592
0.848	Intermediate Similarity	NPC131799
0.8462	Intermediate Similarity	NPC474394
0.8443	Intermediate Similarity	NPC216297
0.8443	Intermediate Similarity	NPC72977
0.8443	Intermediate Similarity	NPC473662
0.8443	Intermediate Similarity	NPC7151
0.843	Intermediate Similarity	NPC41567
0.843	Intermediate Similarity	NPC94637
0.8425	Intermediate Similarity	NPC48248
0.8409	Intermediate Similarity	NPC70380
0.8409	Intermediate Similarity	NPC178467
0.8409	Intermediate Similarity	NPC474771
0.8409	Intermediate Similarity	NPC149372
0.8409	Intermediate Similarity	NPC474849
0.8409	Intermediate Similarity	NPC65837
0.8403	Intermediate Similarity	NPC276111
0.8403	Intermediate Similarity	NPC118288
0.84	Intermediate Similarity	NPC234890
0.84	Intermediate Similarity	NPC173978
0.84	Intermediate Similarity	NPC74507
0.8397	Intermediate Similarity	NPC229638
0.8397	Intermediate Similarity	NPC267539
0.8397	Intermediate Similarity	NPC161632
0.8397	Intermediate Similarity	NPC204257
0.8397	Intermediate Similarity	NPC254832
0.8397	Intermediate Similarity	NPC29317
0.8397	Intermediate Similarity	NPC176102
0.8397	Intermediate Similarity	NPC71108
0.8387	Intermediate Similarity	NPC46634
0.8387	Intermediate Similarity	NPC300274
0.8385	Intermediate Similarity	NPC48036
0.8385	Intermediate Similarity	NPC157478
0.8385	Intermediate Similarity	NPC295406
0.8385	Intermediate Similarity	NPC200422
0.8385	Intermediate Similarity	NPC289572
0.8372	Intermediate Similarity	NPC219892
0.8372	Intermediate Similarity	NPC189823
0.8361	Intermediate Similarity	NPC195262
0.8361	Intermediate Similarity	NPC188814
0.8346	Intermediate Similarity	NPC212693
0.8346	Intermediate Similarity	NPC33144
0.8346	Intermediate Similarity	NPC9121
0.8346	Intermediate Similarity	NPC191835
0.8346	Intermediate Similarity	NPC177307
0.8346	Intermediate Similarity	NPC471530
0.8346	Intermediate Similarity	NPC4214
0.8346	Intermediate Similarity	NPC475974
0.8346	Intermediate Similarity	NPC94248
0.8346	Intermediate Similarity	NPC478200
0.8333	Intermediate Similarity	NPC291454
0.8333	Intermediate Similarity	NPC287473
0.8321	Intermediate Similarity	NPC282780
0.8321	Intermediate Similarity	NPC166480
0.832	Intermediate Similarity	NPC375356
0.8319	Intermediate Similarity	NPC223004
0.8305	Intermediate Similarity	NPC228609
0.8296	Intermediate Similarity	NPC478217
0.8296	Intermediate Similarity	NPC313123
0.8293	Intermediate Similarity	NPC260837
0.8284	Intermediate Similarity	NPC295339
0.8279	Intermediate Similarity	NPC474890
0.8279	Intermediate Similarity	NPC161943
0.8279	Intermediate Similarity	NPC273282
0.8276	Intermediate Similarity	NPC34715
0.8271	Intermediate Similarity	NPC62272
0.8268	Intermediate Similarity	NPC473751
0.8268	Intermediate Similarity	NPC3224
0.8268	Intermediate Similarity	NPC231774
0.8258	Intermediate Similarity	NPC249272
0.8258	Intermediate Similarity	NPC278375
0.8258	Intermediate Similarity	NPC72918
0.8254	Intermediate Similarity	NPC68756
0.8254	Intermediate Similarity	NPC142956
0.8254	Intermediate Similarity	NPC152525
0.8254	Intermediate Similarity	NPC310540
0.825	Intermediate Similarity	NPC114918
0.8244	Intermediate Similarity	NPC153783
0.8244	Intermediate Similarity	NPC472591
0.824	Intermediate Similarity	NPC217756
0.8235	Intermediate Similarity	NPC250755
0.8235	Intermediate Similarity	NPC231717
0.8231	Intermediate Similarity	NPC85342
0.8226	Intermediate Similarity	NPC241001
0.8226	Intermediate Similarity	NPC149246
0.8226	Intermediate Similarity	NPC190971
0.8222	Intermediate Similarity	NPC168471
0.8222	Intermediate Similarity	NPC158472
0.8217	Intermediate Similarity	NPC34414
0.8217	Intermediate Similarity	NPC109123
0.8217	Intermediate Similarity	NPC146647
0.8211	Intermediate Similarity	NPC232178
0.8209	Intermediate Similarity	NPC472403
0.8209	Intermediate Similarity	NPC61590
0.8209	Intermediate Similarity	NPC472602
0.8203	Intermediate Similarity	NPC71525
0.8195	Intermediate Similarity	NPC158481
0.8195	Intermediate Similarity	NPC472308
0.8195	Intermediate Similarity	NPC223836
0.8195	Intermediate Similarity	NPC191976
0.819	Intermediate Similarity	NPC187913
0.8189	Intermediate Similarity	NPC103540
0.8182	Intermediate Similarity	NPC12070
0.8182	Intermediate Similarity	NPC270899
0.8182	Intermediate Similarity	NPC175943
0.8175	Intermediate Similarity	NPC174991
0.8175	Intermediate Similarity	NPC478202
0.8168	Intermediate Similarity	NPC246693
0.8168	Intermediate Similarity	NPC110609
0.8168	Intermediate Similarity	NPC242358
0.8162	Intermediate Similarity	NPC158634
0.8162	Intermediate Similarity	NPC478201
0.8162	Intermediate Similarity	NPC471444
0.8162	Intermediate Similarity	NPC67650
0.8162	Intermediate Similarity	NPC53649
0.8162	Intermediate Similarity	NPC1704
0.8162	Intermediate Similarity	NPC257003
0.8162	Intermediate Similarity	NPC475730
0.8162	Intermediate Similarity	NPC472035
0.816	Intermediate Similarity	NPC196976

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 NPC115188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	917
0.2-0.3	1425
0.3-0.4	2553
0.4-0.5	2206
0.5-0.6	1212
0.6-0.7	475
0.7-0.8	83
0.8-0.85	8
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8684	High Similarity	NPD74	Approved
0.8684	High Similarity	NPD9266	Approved
0.8596	High Similarity	NPD9264	Approved
0.8596	High Similarity	NPD9263	Approved
0.8596	High Similarity	NPD9267	Approved
0.8571	High Similarity	NPD405	Clinical (unspecified phase)
0.8571	High Similarity	NPD9493	Approved
0.8455	Intermediate Similarity	NPD1201	Approved
0.8333	Intermediate Similarity	NPD1164	Approved
0.8271	Intermediate Similarity	NPD5406	Approved
0.8271	Intermediate Similarity	NPD5405	Approved
0.8271	Intermediate Similarity	NPD5408	Approved
0.8271	Intermediate Similarity	NPD5404	Approved
0.8246	Intermediate Similarity	NPD9261	Approved
0.8189	Intermediate Similarity	NPD1470	Approved
0.8134	Intermediate Similarity	NPD2935	Discontinued
0.8099	Intermediate Similarity	NPD9281	Approved
0.7953	Intermediate Similarity	NPD9717	Approved
0.7883	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD1203	Approved
0.7744	Intermediate Similarity	NPD411	Approved
0.771	Intermediate Similarity	NPD2798	Approved
0.7704	Intermediate Similarity	NPD447	Suspended
0.7681	Intermediate Similarity	NPD2346	Discontinued
0.7667	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD2797	Approved
0.763	Intermediate Similarity	NPD943	Approved
0.7606	Intermediate Similarity	NPD7390	Discontinued
0.7603	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6832	Phase 2
0.7578	Intermediate Similarity	NPD4626	Approved
0.7578	Intermediate Similarity	NPD3019	Approved
0.7578	Intermediate Similarity	NPD2932	Approved
0.7565	Intermediate Similarity	NPD844	Approved
0.7552	Intermediate Similarity	NPD2532	Approved
0.7552	Intermediate Similarity	NPD2533	Approved
0.7552	Intermediate Similarity	NPD2534	Approved
0.7536	Intermediate Similarity	NPD2799	Discontinued
0.752	Intermediate Similarity	NPD5951	Approved
0.75	Intermediate Similarity	NPD288	Approved
0.75	Intermediate Similarity	NPD7819	Suspended
0.7481	Intermediate Similarity	NPD3764	Approved
0.7458	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6663	Approved
0.7426	Intermediate Similarity	NPD520	Approved
0.7422	Intermediate Similarity	NPD9545	Approved
0.7422	Intermediate Similarity	NPD1759	Phase 1
0.7413	Intermediate Similarity	NPD3300	Phase 2
0.7398	Intermediate Similarity	NPD4750	Phase 3
0.7394	Intermediate Similarity	NPD3750	Approved
0.7394	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD5736	Approved
0.7372	Intermediate Similarity	NPD1240	Approved
0.736	Intermediate Similarity	NPD7635	Approved
0.7353	Intermediate Similarity	NPD2313	Discontinued
0.7353	Intermediate Similarity	NPD3268	Approved
0.7347	Intermediate Similarity	NPD3226	Approved
0.7344	Intermediate Similarity	NPD1758	Phase 1
0.7319	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1283	Approved
0.7286	Intermediate Similarity	NPD4308	Phase 3
0.7286	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD9258	Approved
0.7281	Intermediate Similarity	NPD9256	Approved
0.7273	Intermediate Similarity	NPD7003	Approved
0.7273	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9269	Phase 2
0.7273	Intermediate Similarity	NPD6232	Discontinued
0.7266	Intermediate Similarity	NPD1607	Approved
0.725	Intermediate Similarity	NPD846	Approved
0.725	Intermediate Similarity	NPD940	Approved
0.7244	Intermediate Similarity	NPD7473	Discontinued
0.7241	Intermediate Similarity	NPD845	Approved
0.7234	Intermediate Similarity	NPD1551	Phase 2
0.7231	Intermediate Similarity	NPD9268	Approved
0.7231	Intermediate Similarity	NPD5691	Approved
0.723	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD3020	Approved
0.72	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1930	Approved
0.719	Intermediate Similarity	NPD1929	Approved
0.7188	Intermediate Similarity	NPD256	Approved
0.7188	Intermediate Similarity	NPD255	Approved
0.7185	Intermediate Similarity	NPD1019	Discontinued
0.7183	Intermediate Similarity	NPD2344	Approved
0.7179	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7768	Phase 2
0.7163	Intermediate Similarity	NPD1510	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7119	Intermediate Similarity	NPD2859	Approved
0.7119	Intermediate Similarity	NPD2860	Approved
0.7097	Intermediate Similarity	NPD2342	Discontinued
0.709	Intermediate Similarity	NPD1755	Approved
0.7083	Intermediate Similarity	NPD2066	Phase 3
0.7075	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD230	Phase 1
0.7068	Intermediate Similarity	NPD1281	Approved
0.7042	Intermediate Similarity	NPD3748	Approved
0.704	Intermediate Similarity	NPD2182	Approved
0.7034	Intermediate Similarity	NPD2934	Approved
0.7034	Intermediate Similarity	NPD2933	Approved
0.7034	Intermediate Similarity	NPD8166	Discontinued
0.7013	Intermediate Similarity	NPD7075	Discontinued
0.7013	Intermediate Similarity	NPD3749	Approved
0.7	Intermediate Similarity	NPD4307	Phase 2
0.6993	Remote Similarity	NPD6100	Approved
0.6993	Remote Similarity	NPD6099	Approved
0.6993	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3496	Discontinued
0.6992	Remote Similarity	NPD3023	Approved
0.6992	Remote Similarity	NPD164	Approved
0.6992	Remote Similarity	NPD3026	Approved
0.6986	Remote Similarity	NPD2309	Approved
0.6985	Remote Similarity	NPD3266	Approved
0.6985	Remote Similarity	NPD3267	Approved
0.6984	Remote Similarity	NPD3022	Approved
0.6984	Remote Similarity	NPD3021	Approved
0.6983	Remote Similarity	NPD1089	Approved
0.6983	Remote Similarity	NPD1090	Approved
0.6983	Remote Similarity	NPD1086	Approved
0.6975	Remote Similarity	NPD1809	Phase 2
0.6972	Remote Similarity	NPD9279	Approved
0.697	Remote Similarity	NPD3025	Approved
0.697	Remote Similarity	NPD3024	Approved
0.695	Remote Similarity	NPD1933	Approved
0.6949	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD258	Approved
0.6934	Remote Similarity	NPD257	Approved
0.693	Remote Similarity	NPD9257	Approved
0.693	Remote Similarity	NPD9259	Approved
0.6928	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6671	Approved
0.6918	Remote Similarity	NPD1196	Approved
0.6917	Remote Similarity	NPD1778	Approved
0.6917	Remote Similarity	NPD17	Approved
0.6913	Remote Similarity	NPD6273	Approved
0.6912	Remote Similarity	NPD1876	Approved
0.6908	Remote Similarity	NPD7411	Suspended
0.6897	Remote Similarity	NPD800	Approved
0.6897	Remote Similarity	NPD1549	Phase 2
0.6892	Remote Similarity	NPD1543	Discontinued
0.6892	Remote Similarity	NPD6799	Approved
0.6892	Remote Similarity	NPD1511	Approved
0.6891	Remote Similarity	NPD1693	Approved
0.6891	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1445	Approved
0.688	Remote Similarity	NPD1444	Approved
0.6879	Remote Similarity	NPD4060	Phase 1
0.6875	Remote Similarity	NPD2796	Approved
0.6875	Remote Similarity	NPD4476	Approved
0.6875	Remote Similarity	NPD4477	Approved
0.687	Remote Similarity	NPD9568	Approved
0.6864	Remote Similarity	NPD1088	Approved
0.6863	Remote Similarity	NPD1934	Approved
0.686	Remote Similarity	NPD9495	Approved
0.6857	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1237	Approved
0.6855	Remote Similarity	NPD5909	Discontinued
0.685	Remote Similarity	NPD1792	Phase 2
0.6849	Remote Similarity	NPD1195	Approved
0.6849	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2629	Approved
0.6842	Remote Similarity	NPD1651	Approved
0.6842	Remote Similarity	NPD6599	Discontinued
0.6835	Remote Similarity	NPD5710	Approved
0.6835	Remote Similarity	NPD5711	Approved
0.6831	Remote Similarity	NPD6355	Discontinued
0.6829	Remote Similarity	NPD1932	Approved
0.6828	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5277	Phase 2
0.6818	Remote Similarity	NPD2801	Approved
0.6815	Remote Similarity	NPD422	Phase 1
0.6814	Remote Similarity	NPD9491	Approved
0.6809	Remote Similarity	NPD8032	Phase 2
0.6807	Remote Similarity	NPD8150	Discontinued
0.6807	Remote Similarity	NPD1202	Approved
0.6803	Remote Similarity	NPD4628	Phase 3
0.6803	Remote Similarity	NPD3400	Discontinued
0.68	Remote Similarity	NPD1512	Approved
0.6788	Remote Similarity	NPD3225	Approved
0.6786	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7008	Discontinued
0.6783	Remote Similarity	NPD6651	Approved
0.6781	Remote Similarity	NPD9277	Approved
0.6781	Remote Similarity	NPD75	Approved
0.6776	Remote Similarity	NPD7458	Discontinued
0.6774	Remote Similarity	NPD3817	Phase 2
0.6774	Remote Similarity	NPD5402	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