NPASS Compound

Structure

CID107240 OpenBabel06191715452D 26 27 0 0 0 0 0 0 0 0999 V2000 0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 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 3.4641 1.0000 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 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 2.5981 -1.5000 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 1.7321 0.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 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 3.4641 -2.0000 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 0.0000 -2.0000 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 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 -1.7321 -2.0000 0.0000 O 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 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 19 2 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 14 1 0 0 0 0 11 18 2 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 20 1 0 0 0 0 16 23 2 0 0 0 0 16 24 1 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 2 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.35
Volume:	543.911
LogP:	4.715
LogD:	4.035
LogS:	-4.998
# Rotatable Bonds:	6
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	5.099
Fsp3:	0.806
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.979
MDCK Permeability:	2.8258213205845095e-05
Pgp-inhibitor:	0.921
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.284

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983
Plasma Protein Binding (PPB):	81.50625610351562%
Volume Distribution (VD):	0.922
Pgp-substrate:	12.81889533996582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.639
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.897
CYP2C9-inhibitor:	0.204
CYP2C9-substrate:	0.397
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.941
CYP3A4-substrate:	0.659

ADMET: Excretion

Clearance (CL):	6.734
Half-life (T1/2):	0.3

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.273
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.637
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.04
Carcinogencity:	0.328
Eye Corrosion:	0.004
Eye Irritation:	0.022
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC107240

Natural Product ID:	NPC107240
*Common Name:**	Longistyline D
IUPAC Name:	4,6-bis(3-methylbut-2-enyl)-5-[(E)-2-phenylethenyl]benzene-1,3-diol
Synonyms:	Longistyline D
Standard InCHIKey:	OKMVXSASFNVYOK-NTCAYCPXSA-N
Standard InCHI:	InChI=1S/C24H28O2/c1-17(2)10-13-21-20(15-12-19-8-6-5-7-9-19)22(14-11-18(3)4)24(26)16-23(21)25/h5-12,15-16,25-26H,13-14H2,1-4H3/b15-12+
SMILES:	CC(=CCc1c(/C=C/c2ccccc2)c(CC=C(C)C)c(cc1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471086
PubChem CID:	18546463
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO27986	Lonchocarpus chiricanus	Species	Fabaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[11421729]
NPO27806	Gossypium hirsutum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27806	Gossypium hirsutum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27684	Stoebe plumosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28024	Rheum palmatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27932	Schistocarpha bicolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4643	Cladophora prolifera	Species	Cladophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27619	Dianella laevis	Species	Hydrobiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27986	Lonchocarpus chiricanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27806	Gossypium hirsutum	Species	Malvaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1381	Organism	Aedes aegypti	Aedes aegypti	Activity	=	6.0	ppm	PMID[490723]

☑ 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 NPC107240 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	332
0.1-0.2	1774
0.2-0.3	4628
0.3-0.4	13301
0.4-0.5	5628
0.5-0.6	6209
0.6-0.7	7779
0.7-0.8	2543
0.8-0.85	330
0.85-0.9	133
0.9-0.95	31
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9717	High Similarity	NPC165770
0.9717	High Similarity	NPC225679
0.9717	High Similarity	NPC476632
0.9717	High Similarity	NPC4493
0.9626	High Similarity	NPC43525
0.9537	High Similarity	NPC117846
0.9434	High Similarity	NPC63698
0.9434	High Similarity	NPC61885
0.9358	High Similarity	NPC263753
0.9346	High Similarity	NPC202647
0.9298	High Similarity	NPC237667
0.9266	High Similarity	NPC166995
0.9259	High Similarity	NPC224870
0.9196	High Similarity	NPC470760
0.9189	High Similarity	NPC246760
0.9189	High Similarity	NPC84999
0.9174	High Similarity	NPC224527
0.9167	High Similarity	NPC19808
0.9167	High Similarity	NPC33728
0.9151	High Similarity	NPC474839
0.9138	High Similarity	NPC53567
0.9107	High Similarity	NPC115808
0.9074	High Similarity	NPC174981
0.9065	High Similarity	NPC248904
0.9057	High Similarity	NPC102216
0.9057	High Similarity	NPC119860
0.9057	High Similarity	NPC241891
0.9057	High Similarity	NPC30506
0.9035	High Similarity	NPC217174
0.9027	High Similarity	NPC277588
0.9	High Similarity	NPC95716
0.9	High Similarity	NPC151537
0.8983	High Similarity	NPC105031
0.8972	High Similarity	NPC134829
0.8972	High Similarity	NPC292452
0.8957	High Similarity	NPC223451
0.8929	High Similarity	NPC249270
0.8919	High Similarity	NPC46940
0.8919	High Similarity	NPC473521
0.8898	High Similarity	NPC224342
0.8889	High Similarity	NPC302681
0.8889	High Similarity	NPC118286
0.8889	High Similarity	NPC39097
0.8889	High Similarity	NPC39664
0.8889	High Similarity	NPC470700
0.8889	High Similarity	NPC109691
0.8879	High Similarity	NPC102639
0.8879	High Similarity	NPC24125
0.887	High Similarity	NPC191866
0.8868	High Similarity	NPC143659
0.8868	High Similarity	NPC100340
0.8839	High Similarity	NPC23804
0.8818	High Similarity	NPC58865
0.8818	High Similarity	NPC186385
0.8818	High Similarity	NPC299568
0.8807	High Similarity	NPC151477
0.8807	High Similarity	NPC232523
0.8807	High Similarity	NPC204901
0.8807	High Similarity	NPC54844
0.8807	High Similarity	NPC158253
0.8803	High Similarity	NPC39029
0.8803	High Similarity	NPC476633
0.8796	High Similarity	NPC246056
0.8796	High Similarity	NPC37802
0.8796	High Similarity	NPC138942
0.8793	High Similarity	NPC282255
0.8785	High Similarity	NPC24404
0.8785	High Similarity	NPC242342
0.8785	High Similarity	NPC146798
0.8785	High Similarity	NPC168829
0.8785	High Similarity	NPC222522
0.8785	High Similarity	NPC106396
0.8785	High Similarity	NPC168303
0.8785	High Similarity	NPC85479
0.8785	High Similarity	NPC168393
0.8785	High Similarity	NPC94351
0.8785	High Similarity	NPC302219
0.8785	High Similarity	NPC71002
0.8785	High Similarity	NPC53051
0.8785	High Similarity	NPC249828
0.8785	High Similarity	NPC313030
0.8783	High Similarity	NPC144343
0.8783	High Similarity	NPC206
0.8774	High Similarity	NPC275053
0.8774	High Similarity	NPC10588
0.8774	High Similarity	NPC248573
0.8774	High Similarity	NPC166761
0.8774	High Similarity	NPC161571
0.8772	High Similarity	NPC261973
0.875	High Similarity	NPC170485
0.8739	High Similarity	NPC13482
0.8739	High Similarity	NPC475018
0.8729	High Similarity	NPC120172
0.8727	High Similarity	NPC95344
0.8727	High Similarity	NPC11554
0.8716	High Similarity	NPC12640
0.8716	High Similarity	NPC201662
0.8716	High Similarity	NPC99836
0.8707	High Similarity	NPC151197
0.8704	High Similarity	NPC218879
0.8704	High Similarity	NPC288411
0.8704	High Similarity	NPC244513
0.8704	High Similarity	NPC227458
0.8692	High Similarity	NPC11280
0.8692	High Similarity	NPC147310
0.8692	High Similarity	NPC294186
0.8692	High Similarity	NPC137415
0.8692	High Similarity	NPC166313
0.8692	High Similarity	NPC72947
0.8692	High Similarity	NPC192032
0.8692	High Similarity	NPC24407
0.8692	High Similarity	NPC284011
0.8684	High Similarity	NPC472893
0.8679	High Similarity	NPC80027
0.8673	High Similarity	NPC261343
0.8673	High Similarity	NPC715
0.8667	High Similarity	NPC113495
0.8632	High Similarity	NPC472071
0.8632	High Similarity	NPC3239
0.8632	High Similarity	NPC69006
0.8624	High Similarity	NPC219286
0.8624	High Similarity	NPC99557
0.8624	High Similarity	NPC117115
0.8621	High Similarity	NPC131118
0.8618	High Similarity	NPC254000
0.8607	High Similarity	NPC215300
0.8596	High Similarity	NPC195922
0.8595	High Similarity	NPC9292
0.8595	High Similarity	NPC145659
0.8585	High Similarity	NPC291789
0.8584	High Similarity	NPC250323
0.8583	High Similarity	NPC97578
0.8583	High Similarity	NPC228503
0.8583	High Similarity	NPC138248
0.8571	High Similarity	NPC141782
0.8548	High Similarity	NPC282508
0.8548	High Similarity	NPC15543
0.8545	High Similarity	NPC21594
0.8545	High Similarity	NPC54765
0.8545	High Similarity	NPC271274
0.8545	High Similarity	NPC67250
0.8534	High Similarity	NPC33270
0.8534	High Similarity	NPC172219
0.8534	High Similarity	NPC304510
0.8534	High Similarity	NPC474933
0.8534	High Similarity	NPC69261
0.8532	High Similarity	NPC238696
0.8525	High Similarity	NPC473221
0.8525	High Similarity	NPC53781
0.8522	High Similarity	NPC474486
0.8522	High Similarity	NPC808
0.8512	High Similarity	NPC105718
0.8512	High Similarity	NPC278955
0.8509	High Similarity	NPC319803
0.8496	Intermediate Similarity	NPC176279
0.8496	Intermediate Similarity	NPC268032
0.8496	Intermediate Similarity	NPC260323
0.8482	Intermediate Similarity	NPC314187
0.8468	Intermediate Similarity	NPC305603
0.8468	Intermediate Similarity	NPC61033
0.8462	Intermediate Similarity	NPC48781
0.8462	Intermediate Similarity	NPC9592
0.8462	Intermediate Similarity	NPC469609
0.8462	Intermediate Similarity	NPC190514
0.8462	Intermediate Similarity	NPC471671
0.8455	Intermediate Similarity	NPC471350
0.8455	Intermediate Similarity	NPC38017
0.8448	Intermediate Similarity	NPC85292
0.8448	Intermediate Similarity	NPC54507
0.8448	Intermediate Similarity	NPC229147
0.8448	Intermediate Similarity	NPC150624
0.8448	Intermediate Similarity	NPC141090
0.8443	Intermediate Similarity	NPC82299
0.8435	Intermediate Similarity	NPC12656
0.8435	Intermediate Similarity	NPC268160
0.8435	Intermediate Similarity	NPC473137
0.8426	Intermediate Similarity	NPC225506
0.8426	Intermediate Similarity	NPC211885
0.8421	Intermediate Similarity	NPC228425
0.8421	Intermediate Similarity	NPC302371
0.8417	Intermediate Similarity	NPC57199
0.8417	Intermediate Similarity	NPC74137
0.8413	Intermediate Similarity	NPC185777
0.8413	Intermediate Similarity	NPC474453
0.8411	Intermediate Similarity	NPC156313
0.8411	Intermediate Similarity	NPC77492
0.8411	Intermediate Similarity	NPC32674
0.8407	Intermediate Similarity	NPC296683
0.8407	Intermediate Similarity	NPC132720
0.84	Intermediate Similarity	NPC160623
0.8396	Intermediate Similarity	NPC26244
0.8396	Intermediate Similarity	NPC274678
0.8393	Intermediate Similarity	NPC262365
0.839	Intermediate Similarity	NPC184302
0.839	Intermediate Similarity	NPC176893
0.839	Intermediate Similarity	NPC469644
0.8387	Intermediate Similarity	NPC471519
0.8387	Intermediate Similarity	NPC471518
0.8387	Intermediate Similarity	NPC92624
0.8387	Intermediate Similarity	NPC16577

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 NPC107240 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	1043
0.2-0.3	1287
0.3-0.4	2982
0.4-0.5	1811
0.5-0.6	1136
0.6-0.7	456
0.7-0.8	85
0.8-0.85	13
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8868	High Similarity	NPD846	Approved
0.8868	High Similarity	NPD940	Approved
0.8818	High Similarity	NPD4750	Phase 3
0.8774	High Similarity	NPD1242	Phase 1
0.8505	High Similarity	NPD3020	Approved
0.8421	Intermediate Similarity	NPD7635	Approved
0.8396	Intermediate Similarity	NPD2859	Approved
0.8396	Intermediate Similarity	NPD2860	Approved
0.8387	Intermediate Similarity	NPD4625	Phase 3
0.8304	Intermediate Similarity	NPD2342	Discontinued
0.8302	Intermediate Similarity	NPD2934	Approved
0.8302	Intermediate Similarity	NPD2933	Approved
0.8158	Intermediate Similarity	NPD3021	Approved
0.8158	Intermediate Similarity	NPD3022	Approved
0.8056	Intermediate Similarity	NPD1809	Phase 2
0.8056	Intermediate Similarity	NPD844	Approved
0.8049	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD845	Approved
0.8031	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD288	Approved
0.7963	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD1610	Phase 2
0.7874	Intermediate Similarity	NPD4908	Phase 1
0.7851	Intermediate Similarity	NPD3091	Approved
0.7803	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD4093	Discontinued
0.776	Intermediate Similarity	NPD4749	Approved
0.7742	Intermediate Similarity	NPD3092	Approved
0.7724	Intermediate Similarity	NPD2286	Discontinued
0.7724	Intermediate Similarity	NPD3019	Approved
0.7724	Intermediate Similarity	NPD2932	Approved
0.7724	Intermediate Similarity	NPD4059	Approved
0.7717	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD1548	Phase 1
0.7674	Intermediate Similarity	NPD3027	Phase 3
0.7638	Intermediate Similarity	NPD3094	Phase 2
0.7638	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7390	Discontinued
0.76	Intermediate Similarity	NPD1201	Approved
0.7597	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD4626	Approved
0.7581	Intermediate Similarity	NPD4589	Approved
0.7561	Intermediate Similarity	NPD5303	Approved
0.7561	Intermediate Similarity	NPD5304	Approved
0.7542	Intermediate Similarity	NPD1792	Phase 2
0.7541	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD497	Approved
0.7519	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4060	Phase 1
0.7481	Intermediate Similarity	NPD5404	Approved
0.7481	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD5408	Approved
0.7481	Intermediate Similarity	NPD5406	Approved
0.7481	Intermediate Similarity	NPD5405	Approved
0.7453	Intermediate Similarity	NPD111	Approved
0.744	Intermediate Similarity	NPD3095	Discontinued
0.744	Intermediate Similarity	NPD1751	Approved
0.7438	Intermediate Similarity	NPD2228	Approved
0.7438	Intermediate Similarity	NPD498	Approved
0.7438	Intermediate Similarity	NPD2229	Approved
0.7438	Intermediate Similarity	NPD495	Approved
0.7438	Intermediate Similarity	NPD2234	Approved
0.7438	Intermediate Similarity	NPD496	Approved
0.7419	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD4097	Suspended
0.7385	Intermediate Similarity	NPD2861	Phase 2
0.7368	Intermediate Similarity	NPD943	Approved
0.7368	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1613	Approved
0.7364	Intermediate Similarity	NPD1470	Approved
0.7323	Intermediate Similarity	NPD422	Phase 1
0.7317	Intermediate Similarity	NPD6671	Approved
0.7304	Intermediate Similarity	NPD3028	Approved
0.7295	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6407	Approved
0.7293	Intermediate Similarity	NPD6405	Approved
0.7288	Intermediate Similarity	NPD1444	Approved
0.7288	Intermediate Similarity	NPD1445	Approved
0.7287	Intermediate Similarity	NPD6696	Suspended
0.7259	Intermediate Similarity	NPD2568	Approved
0.7252	Intermediate Similarity	NPD3018	Phase 2
0.7252	Intermediate Similarity	NPD5736	Approved
0.7239	Intermediate Similarity	NPD1555	Discontinued
0.7236	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD1164	Approved
0.7226	Intermediate Similarity	NPD6100	Approved
0.7226	Intermediate Similarity	NPD6099	Approved
0.7222	Intermediate Similarity	NPD1651	Approved
0.7222	Intermediate Similarity	NPD5691	Approved
0.7209	Intermediate Similarity	NPD1669	Approved
0.7194	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD709	Approved
0.7176	Intermediate Similarity	NPD2195	Approved
0.7176	Intermediate Similarity	NPD2194	Approved
0.717	Intermediate Similarity	NPD9089	Approved
0.7165	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1283	Approved
0.7154	Intermediate Similarity	NPD5283	Phase 1
0.7143	Intermediate Similarity	NPD5155	Approved
0.7143	Intermediate Similarity	NPD5156	Approved
0.7143	Intermediate Similarity	NPD7330	Discontinued
0.7143	Intermediate Similarity	NPD3750	Approved
0.7121	Intermediate Similarity	NPD3637	Approved
0.7121	Intermediate Similarity	NPD3635	Approved
0.7121	Intermediate Similarity	NPD3636	Approved
0.7111	Intermediate Similarity	NPD1240	Approved
0.7111	Intermediate Similarity	NPD2238	Phase 2
0.7109	Intermediate Similarity	NPD3026	Approved
0.7109	Intermediate Similarity	NPD3023	Approved
0.7101	Intermediate Similarity	NPD2935	Discontinued
0.7099	Intermediate Similarity	NPD1133	Approved
0.7099	Intermediate Similarity	NPD1135	Approved
0.7099	Intermediate Similarity	NPD1134	Approved
0.7099	Intermediate Similarity	NPD1129	Approved
0.7099	Intermediate Similarity	NPD1131	Approved
0.709	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3024	Approved
0.7087	Intermediate Similarity	NPD3025	Approved
0.708	Intermediate Similarity	NPD3555	Approved
0.708	Intermediate Similarity	NPD3552	Approved
0.708	Intermediate Similarity	NPD3554	Approved
0.708	Intermediate Similarity	NPD3553	Approved
0.7077	Intermediate Similarity	NPD2982	Phase 2
0.7077	Intermediate Similarity	NPD2983	Phase 2
0.7075	Intermediate Similarity	NPD9093	Approved
0.7068	Intermediate Similarity	NPD2606	Approved
0.7068	Intermediate Similarity	NPD2605	Approved
0.7063	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4624	Approved
0.7037	Intermediate Similarity	NPD6663	Approved
0.7034	Intermediate Similarity	NPD9500	Approved
0.7029	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7819	Suspended
0.7021	Intermediate Similarity	NPD3892	Phase 2
0.7016	Intermediate Similarity	NPD1398	Phase 1
0.7016	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1607	Approved
0.7	Intermediate Similarity	NPD2230	Approved
0.7	Intermediate Similarity	NPD2981	Phase 2
0.7	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2233	Approved
0.7	Intermediate Similarity	NPD2232	Approved
0.6993	Remote Similarity	NPD7041	Phase 2
0.6993	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD228	Approved
0.6984	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7340	Approved
0.6983	Remote Similarity	NPD9273	Approved
0.697	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4103	Phase 2
0.6963	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4659	Approved
0.694	Remote Similarity	NPD3595	Approved
0.694	Remote Similarity	NPD3594	Approved
0.6929	Remote Similarity	NPD4721	Approved
0.6929	Remote Similarity	NPD4726	Approved
0.6929	Remote Similarity	NPD4725	Approved
0.6928	Remote Similarity	NPD6232	Discontinued
0.6923	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1281	Approved
0.6923	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1611	Approved
0.6917	Remote Similarity	NPD6584	Phase 3
0.6913	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1510	Phase 2
0.6901	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2420	Approved
0.6875	Remote Similarity	NPD2421	Approved
0.687	Remote Similarity	NPD2562	Approved
0.687	Remote Similarity	NPD2561	Approved
0.6861	Remote Similarity	NPD3620	Phase 2
0.6861	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3143	Discontinued
0.6846	Remote Similarity	NPD37	Approved
0.6842	Remote Similarity	NPD3055	Approved
0.6842	Remote Similarity	NPD2797	Approved
0.6842	Remote Similarity	NPD3053	Approved
0.6838	Remote Similarity	NPD3764	Approved
0.6833	Remote Similarity	NPD9608	Approved
0.6833	Remote Similarity	NPD9610	Approved
0.6829	Remote Similarity	NPD5451	Approved
0.6829	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7447	Phase 1
0.6828	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD2533	Approved
0.6828	Remote Similarity	NPD2534	Approved
0.6828	Remote Similarity	NPD2532	Approved
0.6828	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD1793	Approved
0.6825	Remote Similarity	NPD1791	Approved
0.6818	Remote Similarity	NPD5327	Phase 3
0.6812	Remote Similarity	NPD5735	Approved
0.6812	Remote Similarity	NPD5123	Clinical (unspecified phase)

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