NPASS Compound

Structure

NPC471554 OpenBabel07101718312D 29 29 0 0 1 0 0 0 0 0999 V2000 1.2781 -9.1364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6511 -9.0352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7370 -5.1216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6665 -8.4161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 -2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0917 -5.1727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4190 -2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8838 -4.1945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3486 -5.8418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8133 -7.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8623 -7.1801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6270 -3.5254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5565 -6.8199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1191 -7.8492 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5780 -3.8344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5075 -7.1290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3271 -8.8273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8319 -7.5402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3212 -3.1653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2507 -6.4598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0180 -9.7784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7859 -4.8126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7155 -8.1071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 27 1 0 0 0 0 4 28 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 1 0 0 0 0 8 17 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 14 29 1 0 0 0 0 15 16 2 0 0 0 0 15 29 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 1 0 0 0 20 24 2 0 0 0 0 20 27 1 0 0 0 0 21 25 2 0 0 0 0 21 28 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.21
Volume:	426.225
LogP:	2.684
LogD:	2.605
LogS:	-3.393
# Rotatable Bonds:	14
TPSA:	106.2
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	4.188
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.552
MDCK Permeability:	3.353810097905807e-05
Pgp-inhibitor:	0.843
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.176
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.648
Plasma Protein Binding (PPB):	80.51667022705078%
Volume Distribution (VD):	2.064
Pgp-substrate:	19.995824813842773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.468
CYP2C19-substrate:	0.283
CYP2C9-inhibitor:	0.762
CYP2C9-substrate:	0.144
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.34
CYP3A4-inhibitor:	0.649
CYP3A4-substrate:	0.27

ADMET: Excretion

Clearance (CL):	10.638
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.081
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.562
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.201
Carcinogencity:	0.699
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC471554

Natural Product ID:	NPC471554
*Common Name:**	Dimethyl (Z,6E)-2-[(3S)-3,4-Dihydroxy-4-Methylpentyl]-6-[3-(Furan-3-Yl)Propylidene]Hept-2-Enedioate
IUPAC Name:	dimethyl (Z,6E)-2-[(3S)-3,4-dihydroxy-4-methylpentyl]-6-[3-(furan-3-yl)propylidene]hept-2-enedioate
Synonyms:
Standard InCHIKey:	WILPRVDBMLKDJM-QRAIHLCSSA-N
Standard InCHI:	InChI=1S/C22H32O7/c1-22(2,26)19(23)12-11-18(21(25)28-4)10-6-9-17(20(24)27-3)8-5-7-16-13-14-29-15-16/h8,10,13-15,19,23,26H,5-7,9,11-12H2,1-4H3/b17-8+,18-10-/t19-/m0/s1
SMILES:	CC(C)(C(CCC(=CCCC(=CCCC1=COC=C1)C(=O)OC)C(=O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256555
PubChem CID:	24799151
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
NPO12372	Baccharis thymifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18232640]
NPO12372	Baccharis thymifolia	Species	Asteraceae	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
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Activity	=	10.0	day	PMID[572603]

☑ 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 NPC471554 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	242
0.1-0.2	1099
0.2-0.3	3714
0.3-0.4	8384
0.4-0.5	11416
0.5-0.6	8138
0.6-0.7	8639
0.7-0.8	970
0.8-0.85	61
0.85-0.9	26
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473355
1.0	High Similarity	NPC471573
1.0	High Similarity	NPC471501
0.9516	High Similarity	NPC17681
0.944	High Similarity	NPC45358
0.944	High Similarity	NPC97740
0.9344	High Similarity	NPC471559
0.9194	High Similarity	NPC137570
0.904	High Similarity	NPC474830
0.904	High Similarity	NPC476016
0.9032	High Similarity	NPC474829
0.8984	High Similarity	NPC471545
0.8984	High Similarity	NPC471544
0.8984	High Similarity	NPC473344
0.896	High Similarity	NPC474260
0.896	High Similarity	NPC329922
0.896	High Similarity	NPC81912
0.896	High Similarity	NPC329694
0.8871	High Similarity	NPC475818
0.8843	High Similarity	NPC208906
0.8843	High Similarity	NPC144745
0.8819	High Similarity	NPC474279
0.8819	High Similarity	NPC474438
0.879	High Similarity	NPC471549
0.879	High Similarity	NPC473379
0.878	High Similarity	NPC474817
0.873	High Similarity	NPC71274
0.873	High Similarity	NPC75557
0.872	High Similarity	NPC476351
0.864	High Similarity	NPC289911
0.864	High Similarity	NPC283284
0.8636	High Similarity	NPC14650
0.8583	High Similarity	NPC1811
0.8583	High Similarity	NPC26157
0.8561	High Similarity	NPC288209
0.856	High Similarity	NPC474136
0.8485	Intermediate Similarity	NPC474425
0.8485	Intermediate Similarity	NPC474407
0.8485	Intermediate Similarity	NPC474426
0.8473	Intermediate Similarity	NPC89133
0.8467	Intermediate Similarity	NPC121158
0.844	Intermediate Similarity	NPC125182
0.844	Intermediate Similarity	NPC69647
0.8433	Intermediate Similarity	NPC303217
0.8403	Intermediate Similarity	NPC471521
0.8403	Intermediate Similarity	NPC473356
0.84	Intermediate Similarity	NPC473969
0.8387	Intermediate Similarity	NPC131801
0.837	Intermediate Similarity	NPC473268
0.8347	Intermediate Similarity	NPC105249
0.8345	Intermediate Similarity	NPC137295
0.8333	Intermediate Similarity	NPC177331
0.8321	Intermediate Similarity	NPC67003
0.8298	Intermediate Similarity	NPC255414
0.8286	Intermediate Similarity	NPC5676
0.8268	Intermediate Similarity	NPC1848
0.8248	Intermediate Similarity	NPC107571
0.8248	Intermediate Similarity	NPC90953
0.8235	Intermediate Similarity	NPC186626
0.8217	Intermediate Similarity	NPC243269
0.8214	Intermediate Similarity	NPC251865
0.8203	Intermediate Similarity	NPC477967
0.8203	Intermediate Similarity	NPC263870
0.8188	Intermediate Similarity	NPC90296
0.8175	Intermediate Similarity	NPC187547
0.8175	Intermediate Similarity	NPC21831
0.8169	Intermediate Similarity	NPC471174
0.8169	Intermediate Similarity	NPC216755
0.8143	Intermediate Similarity	NPC254198
0.8143	Intermediate Similarity	NPC80635
0.8138	Intermediate Similarity	NPC121615
0.8138	Intermediate Similarity	NPC294511
0.8125	Intermediate Similarity	NPC79557
0.8099	Intermediate Similarity	NPC104924
0.8092	Intermediate Similarity	NPC138139
0.8092	Intermediate Similarity	NPC46536
0.8088	Intermediate Similarity	NPC158525
0.8088	Intermediate Similarity	NPC476947
0.8085	Intermediate Similarity	NPC307346
0.8085	Intermediate Similarity	NPC261733
0.8085	Intermediate Similarity	NPC267004
0.8085	Intermediate Similarity	NPC218712
0.808	Intermediate Similarity	NPC28054
0.8077	Intermediate Similarity	NPC118853
0.8056	Intermediate Similarity	NPC472654
0.8042	Intermediate Similarity	NPC250228
0.8041	Intermediate Similarity	NPC194499
0.8041	Intermediate Similarity	NPC45101
0.803	Intermediate Similarity	NPC83178
0.8029	Intermediate Similarity	NPC46896
0.8027	Intermediate Similarity	NPC155939
0.8027	Intermediate Similarity	NPC141538
0.8027	Intermediate Similarity	NPC264943
0.8027	Intermediate Similarity	NPC92979
0.8027	Intermediate Similarity	NPC296807
0.8015	Intermediate Similarity	NPC221798
0.8015	Intermediate Similarity	NPC179354
0.8014	Intermediate Similarity	NPC474378
0.8014	Intermediate Similarity	NPC474219
0.8014	Intermediate Similarity	NPC268905
0.8014	Intermediate Similarity	NPC243577
0.8014	Intermediate Similarity	NPC44577
0.8	Intermediate Similarity	NPC471817
0.8	Intermediate Similarity	NPC228842
0.8	Intermediate Similarity	NPC212257
0.7987	Intermediate Similarity	NPC472779
0.7986	Intermediate Similarity	NPC7388
0.7973	Intermediate Similarity	NPC469485
0.7971	Intermediate Similarity	NPC215109
0.7971	Intermediate Similarity	NPC170604
0.797	Intermediate Similarity	NPC112706
0.797	Intermediate Similarity	NPC207294
0.7969	Intermediate Similarity	NPC4898
0.7953	Intermediate Similarity	NPC217180
0.7953	Intermediate Similarity	NPC312525
0.7943	Intermediate Similarity	NPC184053
0.7941	Intermediate Similarity	NPC218838
0.7939	Intermediate Similarity	NPC188377
0.7939	Intermediate Similarity	NPC65735
0.7933	Intermediate Similarity	NPC470789
0.7933	Intermediate Similarity	NPC477402
0.7931	Intermediate Similarity	NPC195325
0.7931	Intermediate Similarity	NPC234494
0.7929	Intermediate Similarity	NPC148374
0.7929	Intermediate Similarity	NPC282973
0.7919	Intermediate Similarity	NPC197137
0.7919	Intermediate Similarity	NPC173544
0.7919	Intermediate Similarity	NPC472778
0.7919	Intermediate Similarity	NPC88007
0.7919	Intermediate Similarity	NPC7059
0.7919	Intermediate Similarity	NPC472776
0.7919	Intermediate Similarity	NPC472777
0.791	Intermediate Similarity	NPC223063
0.791	Intermediate Similarity	NPC120836
0.7905	Intermediate Similarity	NPC214541
0.7905	Intermediate Similarity	NPC44675
0.7902	Intermediate Similarity	NPC34056
0.7891	Intermediate Similarity	NPC243704
0.7891	Intermediate Similarity	NPC469503
0.7891	Intermediate Similarity	NPC75906
0.7883	Intermediate Similarity	NPC106247
0.7881	Intermediate Similarity	NPC200782
0.7881	Intermediate Similarity	NPC79571
0.7877	Intermediate Similarity	NPC470997
0.7868	Intermediate Similarity	NPC104854
0.7868	Intermediate Similarity	NPC473982
0.7867	Intermediate Similarity	NPC262872
0.7867	Intermediate Similarity	NPC475967
0.7867	Intermediate Similarity	NPC472671
0.7863	Intermediate Similarity	NPC16922
0.7863	Intermediate Similarity	NPC291189
0.7863	Intermediate Similarity	NPC69403
0.7852	Intermediate Similarity	NPC21460
0.7838	Intermediate Similarity	NPC34421
0.7838	Intermediate Similarity	NPC253201
0.7838	Intermediate Similarity	NPC237259
0.7838	Intermediate Similarity	NPC302054
0.7838	Intermediate Similarity	NPC57998
0.7838	Intermediate Similarity	NPC98206
0.7838	Intermediate Similarity	NPC282445
0.7838	Intermediate Similarity	NPC178932
0.7832	Intermediate Similarity	NPC86935
0.7832	Intermediate Similarity	NPC476944
0.7829	Intermediate Similarity	NPC472773
0.7829	Intermediate Similarity	NPC477405
0.782	Intermediate Similarity	NPC23086
0.782	Intermediate Similarity	NPC74612
0.7815	Intermediate Similarity	NPC335761
0.7815	Intermediate Similarity	NPC8389
0.7812	Intermediate Similarity	NPC227660
0.7803	Intermediate Similarity	NPC477038
0.7803	Intermediate Similarity	NPC477965
0.78	Intermediate Similarity	NPC470119
0.78	Intermediate Similarity	NPC299038
0.78	Intermediate Similarity	NPC470118
0.78	Intermediate Similarity	NPC36655
0.78	Intermediate Similarity	NPC475066
0.78	Intermediate Similarity	NPC214495
0.78	Intermediate Similarity	NPC472772
0.78	Intermediate Similarity	NPC187149
0.78	Intermediate Similarity	NPC195954
0.78	Intermediate Similarity	NPC261597
0.7795	Intermediate Similarity	NPC205523
0.7794	Intermediate Similarity	NPC61788
0.7793	Intermediate Similarity	NPC71821
0.7793	Intermediate Similarity	NPC470941
0.7786	Intermediate Similarity	NPC317217
0.7785	Intermediate Similarity	NPC35000
0.7785	Intermediate Similarity	NPC469336
0.7778	Intermediate Similarity	NPC195920
0.7778	Intermediate Similarity	NPC276551
0.777	Intermediate Similarity	NPC147168
0.777	Intermediate Similarity	NPC472672
0.777	Intermediate Similarity	NPC33938
0.777	Intermediate Similarity	NPC246164
0.7763	Intermediate Similarity	NPC211777
0.7763	Intermediate Similarity	NPC68848
0.7763	Intermediate Similarity	NPC263432
0.7763	Intermediate Similarity	NPC472771
0.7763	Intermediate Similarity	NPC207978

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 NPC471554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	962
0.2-0.3	2224
0.3-0.4	2661
0.4-0.5	1916
0.5-0.6	897
0.6-0.7	266
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7817	Intermediate Similarity	NPD4628	Phase 3
0.755	Intermediate Similarity	NPD5761	Phase 2
0.755	Intermediate Similarity	NPD5760	Phase 2
0.7379	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD9545	Approved
0.7273	Intermediate Similarity	NPD9092	Discovery
0.7241	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7033	Discontinued
0.7208	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6799	Approved
0.7169	Intermediate Similarity	NPD8434	Phase 2
0.7163	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1608	Approved
0.708	Intermediate Similarity	NPD9717	Approved
0.707	Intermediate Similarity	NPD7075	Discontinued
0.7055	Intermediate Similarity	NPD1551	Phase 2
0.7039	Intermediate Similarity	NPD920	Approved
0.7032	Intermediate Similarity	NPD6801	Discontinued
0.7021	Intermediate Similarity	NPD6832	Phase 2
0.7014	Intermediate Similarity	NPD6355	Discontinued
0.7013	Intermediate Similarity	NPD6599	Discontinued
0.7	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6764	Approved
0.697	Remote Similarity	NPD6765	Approved
0.6933	Remote Similarity	NPD2354	Approved
0.6933	Remote Similarity	NPD3887	Approved
0.6928	Remote Similarity	NPD5403	Approved
0.6923	Remote Similarity	NPD6798	Discontinued
0.6908	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5401	Approved
0.6892	Remote Similarity	NPD6004	Phase 3
0.6892	Remote Similarity	NPD6005	Phase 3
0.6892	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6002	Phase 3
0.6892	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7819	Suspended
0.6879	Remote Similarity	NPD5647	Approved
0.6867	Remote Similarity	NPD6559	Discontinued
0.6861	Remote Similarity	NPD1778	Approved
0.6861	Remote Similarity	NPD17	Approved
0.6859	Remote Similarity	NPD7411	Suspended
0.6846	Remote Similarity	NPD1549	Phase 2
0.6842	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD9494	Approved
0.6824	Remote Similarity	NPD2796	Approved
0.6813	Remote Similarity	NPD919	Approved
0.6809	Remote Similarity	NPD1203	Approved
0.6809	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3764	Approved
0.6805	Remote Similarity	NPD6785	Approved
0.6805	Remote Similarity	NPD6784	Approved
0.68	Remote Similarity	NPD1243	Approved
0.6797	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD230	Phase 1
0.6779	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2344	Approved
0.6779	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1019	Discontinued
0.6759	Remote Similarity	NPD4062	Phase 3
0.6759	Remote Similarity	NPD6233	Phase 2
0.6757	Remote Similarity	NPD4308	Phase 3
0.6757	Remote Similarity	NPD2799	Discontinued
0.6753	Remote Similarity	NPD6273	Approved
0.675	Remote Similarity	NPD3749	Approved
0.675	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6653	Approved
0.6716	Remote Similarity	NPD1241	Discontinued
0.6707	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2313	Discontinued
0.669	Remote Similarity	NPD2797	Approved
0.669	Remote Similarity	NPD6362	Approved
0.669	Remote Similarity	NPD3268	Approved
0.6688	Remote Similarity	NPD4380	Phase 2
0.6687	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD447	Suspended
0.6667	Remote Similarity	NPD2353	Approved
0.6645	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3750	Approved
0.6645	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2186	Approved
0.6643	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD7843	Approved
0.6641	Remote Similarity	NPD1358	Approved
0.6627	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD2163	Approved
0.6627	Remote Similarity	NPD3818	Discontinued
0.6625	Remote Similarity	NPD5402	Approved
0.6625	Remote Similarity	NPD3817	Phase 2
0.662	Remote Similarity	NPD3225	Approved
0.6605	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1934	Approved
0.6603	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD2309	Approved
0.6599	Remote Similarity	NPD4307	Phase 2
0.6599	Remote Similarity	NPD1240	Approved
0.6596	Remote Similarity	NPD3972	Approved
0.6594	Remote Similarity	NPD1894	Discontinued
0.6591	Remote Similarity	NPD2684	Approved
0.6587	Remote Similarity	NPD5844	Phase 1
0.6584	Remote Similarity	NPD7768	Phase 2
0.6581	Remote Similarity	NPD2533	Approved
0.6581	Remote Similarity	NPD2534	Approved
0.6581	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD2532	Approved
0.6575	Remote Similarity	NPD411	Approved
0.6569	Remote Similarity	NPD9493	Approved
0.6568	Remote Similarity	NPD7685	Pre-registration
0.6565	Remote Similarity	NPD3134	Approved
0.6558	Remote Similarity	NPD7440	Discontinued
0.6556	Remote Similarity	NPD5763	Approved
0.6556	Remote Similarity	NPD5762	Approved
0.6554	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1933	Approved
0.6544	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5049	Phase 3
0.6533	Remote Similarity	NPD1510	Phase 2
0.6533	Remote Similarity	NPD3748	Approved
0.6522	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7458	Discontinued
0.6519	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD3226	Approved
0.6515	Remote Similarity	NPD290	Approved
0.6515	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD970	Clinical (unspecified phase)
0.651	Remote Similarity	NPD1607	Approved
0.6507	Remote Similarity	NPD7095	Approved
0.6496	Remote Similarity	NPD7157	Approved
0.6494	Remote Similarity	NPD6190	Approved
0.649	Remote Similarity	NPD2935	Discontinued
0.649	Remote Similarity	NPD2239	Approved
0.649	Remote Similarity	NPD2240	Approved
0.6488	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3142	Approved
0.6486	Remote Similarity	NPD3140	Approved
0.6474	Remote Similarity	NPD4661	Approved
0.6474	Remote Similarity	NPD4662	Approved
0.6467	Remote Similarity	NPD7097	Phase 1
0.646	Remote Similarity	NPD8455	Phase 2
0.6458	Remote Similarity	NPD3267	Approved
0.6458	Remote Similarity	NPD3266	Approved
0.6454	Remote Similarity	NPD3496	Discontinued
0.6452	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7074	Phase 3
0.6447	Remote Similarity	NPD1471	Phase 3
0.6447	Remote Similarity	NPD2346	Discontinued
0.6443	Remote Similarity	NPD5124	Phase 1
0.6443	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6386	Approved
0.6438	Remote Similarity	NPD6385	Approved
0.6429	Remote Similarity	NPD4110	Phase 3
0.6429	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1247	Approved
0.6424	Remote Similarity	NPD8127	Discontinued
0.6424	Remote Similarity	NPD7199	Phase 2
0.6414	Remote Similarity	NPD2798	Approved
0.6412	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD1091	Approved
0.6407	Remote Similarity	NPD6166	Phase 2
0.6407	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD4534	Discontinued
0.6405	Remote Similarity	NPD2424	Discontinued
0.6405	Remote Similarity	NPD5958	Discontinued
0.6391	Remote Similarity	NPD7054	Approved
0.6386	Remote Similarity	NPD6808	Phase 2
0.6376	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5494	Approved
0.6364	Remote Similarity	NPD1481	Phase 2
0.6364	Remote Similarity	NPD1652	Phase 2
0.6358	Remote Similarity	NPD2801	Approved
0.6353	Remote Similarity	NPD7472	Approved
0.6351	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD2182	Approved
0.6338	Remote Similarity	NPD3847	Discontinued
0.6335	Remote Similarity	NPD958	Approved
0.6333	Remote Similarity	NPD4340	Discontinued
0.6331	Remote Similarity	NPD7177	Discontinued
0.6322	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD5353	Approved
0.6312	Remote Similarity	NPD5585	Approved
0.6306	Remote Similarity	NPD1511	Approved
0.6301	Remote Similarity	NPD8313	Approved
0.6301	Remote Similarity	NPD8312	Approved
0.6296	Remote Similarity	NPD7577	Discontinued
0.6296	Remote Similarity	NPD2067	Discontinued
0.6294	Remote Similarity	NPD7286	Phase 2
0.6294	Remote Similarity	NPD422	Phase 1
0.6294	Remote Similarity	NPD1535	Discovery
0.6289	Remote Similarity	NPD1670	Discontinued
0.6284	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD7251	Discontinued
0.6277	Remote Similarity	NPD5535	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