NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	642.26
Volume:	658.545
LogP:	2.947
LogD:	2.893
LogS:	-3.885
# Rotatable Bonds:	16
TPSA:	177.81
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.06
Synthetic Accessibility Score:	2.954
Fsp3:	0.222
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.02
MDCK Permeability:	9.74161048361566e-06
Pgp-inhibitor:	0.937
Pgp-substrate:	0.632
Human Intestinal Absorption (HIA):	0.835
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	99.05384063720703%
Volume Distribution (VD):	0.387
Pgp-substrate:	1.0358495712280273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.512
CYP1A2-substrate:	0.878
CYP2C19-inhibitor:	0.519
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.877
CYP2C9-substrate:	0.91
CYP2D6-inhibitor:	0.596
CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.871
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	9.508
Half-life (T1/2):	0.952

ADMET: Toxicity

hERG Blockers:	0.44
Human Hepatotoxicity (H-HT):	0.402
Drug-inuced Liver Injury (DILI):	0.129
AMES Toxicity:	0.487
Rat Oral Acute Toxicity:	0.116
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.952
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC107588

Natural Product ID:	NPC107588
*Common Name:**	Methyl Cis-Ferulate
IUPAC Name:	methyl (Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	AUJXJFHANFIVKH-XQRVVYSFSA-N
Standard InCHI:	InChI=1S/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3/b6-4-
SMILES:	COC(=O)/C=Cc1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2287145
PubChem CID:	10176654
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	seed	n.a.	PMID[11540412]
NPO28230	Stemona japonica	Species	Stemonaceae	Eukaryota	stems and leaves	n.a.	n.a.	PMID[18163592]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28230	Stemona japonica	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28230	Stemona japonica	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18120	Radix rehmanniae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28230	Stemona japonica	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28230	Stemona japonica	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24778	Sesamum orientale	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5895	Hibiscus taiwanensis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28230	Stemona japonica	Species	Stemonaceae	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
ED50	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4225	Organism	Puccinia graminis f. sp. tritici	Puccinia graminis f. sp. tritici	ED50	=	180.0	pg/ml	PMID[500157]
NPT4226	Organism	Puccinia coronata	Puccinia coronata	ED50	=	5570.0	pg/ml	PMID[500157]

☑ 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 NPC107588 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	271
0.1-0.2	1706
0.2-0.3	5468
0.3-0.4	12306
0.4-0.5	5035
0.5-0.6	5776
0.6-0.7	9056
0.7-0.8	2580
0.8-0.85	330
0.85-0.9	107
0.9-0.95	52
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC70744
1.0	High Similarity	NPC137537
1.0	High Similarity	NPC272471
1.0	High Similarity	NPC164706
0.9821	High Similarity	NPC202474
0.9735	High Similarity	NPC204466
0.9649	High Similarity	NPC70752
0.9646	High Similarity	NPC2058
0.9636	High Similarity	NPC294941
0.9402	High Similarity	NPC246704
0.9402	High Similarity	NPC60517
0.9402	High Similarity	NPC20443
0.9402	High Similarity	NPC146886
0.9381	High Similarity	NPC39793
0.9364	High Similarity	NPC226250
0.9322	High Similarity	NPC300326
0.9322	High Similarity	NPC289459
0.9322	High Similarity	NPC58279
0.9298	High Similarity	NPC124916
0.9244	High Similarity	NPC120225
0.9244	High Similarity	NPC213552
0.9224	High Similarity	NPC14007
0.9224	High Similarity	NPC60962
0.9224	High Similarity	NPC189844
0.9224	High Similarity	NPC224814
0.9224	High Similarity	NPC109083
0.9224	High Similarity	NPC269843
0.9217	High Similarity	NPC37858
0.9196	High Similarity	NPC95381
0.9182	High Similarity	NPC246358
0.9182	High Similarity	NPC233731
0.9182	High Similarity	NPC7097
0.9182	High Similarity	NPC36108
0.9145	High Similarity	NPC177291
0.9145	High Similarity	NPC194416
0.9115	High Similarity	NPC328593
0.9115	High Similarity	NPC261453
0.9115	High Similarity	NPC33749
0.9115	High Similarity	NPC217472
0.9091	High Similarity	NPC478215
0.9091	High Similarity	NPC109275
0.9091	High Similarity	NPC110313
0.9068	High Similarity	NPC286573
0.906	High Similarity	NPC158949
0.9052	High Similarity	NPC57501
0.9043	High Similarity	NPC65791
0.9035	High Similarity	NPC474967
0.9035	High Similarity	NPC233669
0.9018	High Similarity	NPC139617
0.9018	High Similarity	NPC173746
0.9018	High Similarity	NPC78918
0.9018	High Similarity	NPC8547
0.9018	High Similarity	NPC156840
0.9018	High Similarity	NPC257124
0.9016	High Similarity	NPC83062
0.9016	High Similarity	NPC48315
0.8992	High Similarity	NPC238810
0.8992	High Similarity	NPC229084
0.8992	High Similarity	NPC18984
0.8992	High Similarity	NPC160900
0.8992	High Similarity	NPC106659
0.8983	High Similarity	NPC310373
0.8966	High Similarity	NPC212743
0.8957	High Similarity	NPC281277
0.8938	High Similarity	NPC131530
0.8909	High Similarity	NPC294902
0.8909	High Similarity	NPC1075
0.8909	High Similarity	NPC1786
0.8908	High Similarity	NPC114298
0.8879	High Similarity	NPC199209
0.8879	High Similarity	NPC212643
0.8879	High Similarity	NPC280001
0.8843	High Similarity	NPC280767
0.8843	High Similarity	NPC271985
0.8833	High Similarity	NPC257976
0.8833	High Similarity	NPC164778
0.8833	High Similarity	NPC242372
0.8833	High Similarity	NPC4181
0.8818	High Similarity	NPC288760
0.8803	High Similarity	NPC205502
0.8803	High Similarity	NPC203124
0.8803	High Similarity	NPC309434
0.8803	High Similarity	NPC275519
0.8803	High Similarity	NPC277460
0.88	High Similarity	NPC111888
0.877	High Similarity	NPC276014
0.8761	High Similarity	NPC179309
0.876	High Similarity	NPC312404
0.876	High Similarity	NPC273686
0.8739	High Similarity	NPC307253
0.873	High Similarity	NPC475468
0.873	High Similarity	NPC159418
0.873	High Similarity	NPC283823
0.8729	High Similarity	NPC299406
0.8729	High Similarity	NPC241634
0.8729	High Similarity	NPC69670
0.8727	High Similarity	NPC2518
0.8718	High Similarity	NPC293619
0.8699	High Similarity	NPC123228
0.8699	High Similarity	NPC123722
0.8699	High Similarity	NPC276466
0.8699	High Similarity	NPC151167
0.8699	High Similarity	NPC5018
0.8699	High Similarity	NPC281020
0.8689	High Similarity	NPC27352
0.8684	High Similarity	NPC195873
0.8684	High Similarity	NPC245552
0.8661	High Similarity	NPC92830
0.8661	High Similarity	NPC471110
0.8661	High Similarity	NPC135127
0.8661	High Similarity	NPC227894
0.8661	High Similarity	NPC111635
0.8655	High Similarity	NPC222175
0.8644	High Similarity	NPC255675
0.8644	High Similarity	NPC470626
0.8632	High Similarity	NPC221049
0.8618	High Similarity	NPC303680
0.8618	High Similarity	NPC84076
0.8618	High Similarity	NPC179777
0.8618	High Similarity	NPC90128
0.8583	High Similarity	NPC470848
0.8583	High Similarity	NPC470849
0.8583	High Similarity	NPC471877
0.8571	High Similarity	NPC311595
0.8571	High Similarity	NPC320987
0.8571	High Similarity	NPC141791
0.8571	High Similarity	NPC24474
0.8571	High Similarity	NPC263386
0.8571	High Similarity	NPC181969
0.856	High Similarity	NPC304622
0.8559	High Similarity	NPC259638
0.8559	High Similarity	NPC52087
0.8559	High Similarity	NPC79672
0.8559	High Similarity	NPC164386
0.8548	High Similarity	NPC117237
0.8548	High Similarity	NPC16651
0.8548	High Similarity	NPC32163
0.8548	High Similarity	NPC203719
0.8545	High Similarity	NPC12714
0.8545	High Similarity	NPC94343
0.8545	High Similarity	NPC310905
0.8537	High Similarity	NPC87113
0.8534	High Similarity	NPC303522
0.8527	High Similarity	NPC157554
0.8527	High Similarity	NPC120852
0.8527	High Similarity	NPC90431
0.8525	High Similarity	NPC163083
0.8512	High Similarity	NPC201777
0.8512	High Similarity	NPC114845
0.8504	High Similarity	NPC245120
0.85	High Similarity	NPC177475
0.85	High Similarity	NPC61516
0.85	High Similarity	NPC232084
0.85	High Similarity	NPC95614
0.85	High Similarity	NPC117780
0.85	High Similarity	NPC165133
0.85	High Similarity	NPC242885
0.85	High Similarity	NPC56214
0.85	High Similarity	NPC232316
0.85	High Similarity	NPC148615
0.85	High Similarity	NPC35071
0.85	High Similarity	NPC247364
0.85	High Similarity	NPC229401
0.85	High Similarity	NPC10932
0.85	High Similarity	NPC227217
0.8492	Intermediate Similarity	NPC66905
0.8492	Intermediate Similarity	NPC285776
0.8492	Intermediate Similarity	NPC172673
0.8475	Intermediate Similarity	NPC268317
0.8475	Intermediate Similarity	NPC193067
0.8462	Intermediate Similarity	NPC148835
0.8462	Intermediate Similarity	NPC52086
0.8462	Intermediate Similarity	NPC76336
0.8462	Intermediate Similarity	NPC126206
0.8462	Intermediate Similarity	NPC139548
0.8462	Intermediate Similarity	NPC95162
0.8462	Intermediate Similarity	NPC20511
0.8455	Intermediate Similarity	NPC253746
0.845	Intermediate Similarity	NPC477301
0.8443	Intermediate Similarity	NPC288238
0.8435	Intermediate Similarity	NPC137685
0.843	Intermediate Similarity	NPC207613
0.8425	Intermediate Similarity	NPC73738
0.8417	Intermediate Similarity	NPC20674
0.8417	Intermediate Similarity	NPC281298
0.8417	Intermediate Similarity	NPC310338
0.8413	Intermediate Similarity	NPC241354
0.8407	Intermediate Similarity	NPC19149
0.8403	Intermediate Similarity	NPC185738
0.8397	Intermediate Similarity	NPC132723
0.8397	Intermediate Similarity	NPC226005
0.8397	Intermediate Similarity	NPC284409
0.8397	Intermediate Similarity	NPC100389
0.8397	Intermediate Similarity	NPC13067
0.8397	Intermediate Similarity	NPC76032
0.8393	Intermediate Similarity	NPC292792
0.8387	Intermediate Similarity	NPC67951
0.8387	Intermediate Similarity	NPC257589
0.8387	Intermediate Similarity	NPC53305
0.8385	Intermediate Similarity	NPC126682

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 NPC107588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	993
0.2-0.3	1742
0.3-0.4	2789
0.4-0.5	1702
0.5-0.6	1023
0.6-0.7	577
0.7-0.8	82
0.8-0.85	5
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9018	High Similarity	NPD228	Approved
0.8992	High Similarity	NPD4379	Clinical (unspecified phase)
0.8548	High Similarity	NPD9494	Approved
0.8496	Intermediate Similarity	NPD1358	Approved
0.8403	Intermediate Similarity	NPD5536	Phase 2
0.8115	Intermediate Similarity	NPD1357	Approved
0.8087	Intermediate Similarity	NPD3134	Approved
0.8	Intermediate Similarity	NPD9296	Approved
0.7917	Intermediate Similarity	NPD5283	Phase 1
0.7903	Intermediate Similarity	NPD4626	Approved
0.7879	Intermediate Similarity	NPD447	Suspended
0.7846	Intermediate Similarity	NPD3027	Phase 3
0.7744	Intermediate Similarity	NPD230	Phase 1
0.7698	Intermediate Similarity	NPD3496	Discontinued
0.7676	Intermediate Similarity	NPD1653	Approved
0.7669	Intermediate Similarity	NPD4060	Phase 1
0.7652	Intermediate Similarity	NPD3145	Approved
0.7652	Intermediate Similarity	NPD3144	Approved
0.7594	Intermediate Similarity	NPD2674	Phase 3
0.7591	Intermediate Similarity	NPD7266	Discontinued
0.7583	Intermediate Similarity	NPD3022	Approved
0.7583	Intermediate Similarity	NPD3021	Approved
0.754	Intermediate Similarity	NPD5691	Approved
0.7518	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2684	Approved
0.75	Intermediate Similarity	NPD422	Phase 1
0.746	Intermediate Similarity	NPD9545	Approved
0.7444	Intermediate Similarity	NPD7095	Approved
0.7436	Intermediate Similarity	NPD291	Approved
0.7424	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD290	Approved
0.7407	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3620	Phase 2
0.7407	Intermediate Similarity	NPD1613	Approved
0.7407	Intermediate Similarity	NPD1558	Phase 1
0.7398	Intermediate Similarity	NPD7843	Approved
0.7395	Intermediate Similarity	NPD9697	Approved
0.7391	Intermediate Similarity	NPD2935	Discontinued
0.7385	Intermediate Similarity	NPD2982	Phase 2
0.7385	Intermediate Similarity	NPD2983	Phase 2
0.7364	Intermediate Similarity	NPD3705	Approved
0.736	Intermediate Similarity	NPD7157	Approved
0.7344	Intermediate Similarity	NPD1778	Approved
0.7328	Intermediate Similarity	NPD1283	Approved
0.7308	Intermediate Similarity	NPD9717	Approved
0.7308	Intermediate Similarity	NPD2981	Phase 2
0.7308	Intermediate Similarity	NPD9269	Phase 2
0.7305	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD8166	Discontinued
0.7305	Intermediate Similarity	NPD4110	Phase 3
0.7302	Intermediate Similarity	NPD9493	Approved
0.7287	Intermediate Similarity	NPD3847	Discontinued
0.7273	Intermediate Similarity	NPD987	Approved
0.7273	Intermediate Similarity	NPD4357	Discontinued
0.726	Intermediate Similarity	NPD824	Approved
0.7258	Intermediate Similarity	NPD5535	Approved
0.7254	Intermediate Similarity	NPD6190	Approved
0.7231	Intermediate Similarity	NPD1535	Discovery
0.7218	Intermediate Similarity	NPD258	Approved
0.7218	Intermediate Similarity	NPD257	Approved
0.7206	Intermediate Similarity	NPD259	Phase 1
0.7206	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1241	Discontinued
0.719	Intermediate Similarity	NPD968	Approved
0.7183	Intermediate Similarity	NPD4628	Phase 3
0.7182	Intermediate Similarity	NPD111	Approved
0.7176	Intermediate Similarity	NPD1481	Phase 2
0.7174	Intermediate Similarity	NPD2653	Approved
0.7174	Intermediate Similarity	NPD2492	Phase 1
0.7174	Intermediate Similarity	NPD6653	Approved
0.7164	Intermediate Similarity	NPD3018	Phase 2
0.7153	Intermediate Similarity	NPD826	Approved
0.7153	Intermediate Similarity	NPD825	Approved
0.7143	Intermediate Similarity	NPD3455	Phase 2
0.7143	Intermediate Similarity	NPD1203	Approved
0.7143	Intermediate Similarity	NPD3111	Phase 1
0.7132	Intermediate Similarity	NPD6798	Discontinued
0.7132	Intermediate Similarity	NPD411	Approved
0.7121	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD9379	Approved
0.712	Intermediate Similarity	NPD9377	Approved
0.7114	Intermediate Similarity	NPD1934	Approved
0.7101	Intermediate Similarity	NPD4340	Discontinued
0.7101	Intermediate Similarity	NPD555	Phase 2
0.7101	Intermediate Similarity	NPD1933	Approved
0.7101	Intermediate Similarity	NPD6355	Discontinued
0.7099	Intermediate Similarity	NPD1281	Approved
0.7097	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6671	Approved
0.7086	Intermediate Similarity	NPD3882	Suspended
0.7086	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4062	Phase 3
0.708	Intermediate Similarity	NPD6233	Phase 2
0.708	Intermediate Similarity	NPD9295	Approved
0.7075	Intermediate Similarity	NPD3687	Approved
0.7075	Intermediate Similarity	NPD3686	Approved
0.7067	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2801	Approved
0.7054	Intermediate Similarity	NPD1894	Discontinued
0.7045	Intermediate Similarity	NPD1608	Approved
0.7042	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD9569	Approved
0.7034	Intermediate Similarity	NPD1511	Approved
0.7016	Intermediate Similarity	NPD556	Approved
0.7008	Intermediate Similarity	NPD9299	Approved
0.7007	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9268	Approved
0.7	Intermediate Similarity	NPD5585	Approved
0.6993	Remote Similarity	NPD3060	Approved
0.6992	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD821	Approved
0.6963	Remote Similarity	NPD5647	Approved
0.6957	Remote Similarity	NPD9365	Approved
0.6954	Remote Similarity	NPD1465	Phase 2
0.694	Remote Similarity	NPD2922	Phase 1
0.694	Remote Similarity	NPD3225	Approved
0.6939	Remote Similarity	NPD1512	Approved
0.6923	Remote Similarity	NPD2933	Approved
0.6923	Remote Similarity	NPD2934	Approved
0.6923	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1242	Phase 1
0.6913	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3817	Phase 2
0.6906	Remote Similarity	NPD4140	Approved
0.6903	Remote Similarity	NPD2821	Approved
0.6897	Remote Similarity	NPD2219	Phase 1
0.6889	Remote Similarity	NPD2797	Approved
0.6884	Remote Similarity	NPD1048	Approved
0.6884	Remote Similarity	NPD5109	Approved
0.6884	Remote Similarity	NPD5111	Phase 2
0.6884	Remote Similarity	NPD5110	Phase 2
0.6883	Remote Similarity	NPD6234	Discontinued
0.6875	Remote Similarity	NPD1652	Phase 2
0.6875	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4739	Approved
0.687	Remote Similarity	NPD1651	Approved
0.6867	Remote Similarity	NPD7028	Phase 2
0.6864	Remote Similarity	NPD2860	Approved
0.6864	Remote Similarity	NPD844	Approved
0.6864	Remote Similarity	NPD2859	Approved
0.6861	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6232	Discontinued
0.6857	Remote Similarity	NPD275	Approved
0.6857	Remote Similarity	NPD274	Approved
0.6853	Remote Similarity	NPD5762	Approved
0.6853	Remote Similarity	NPD1375	Discontinued
0.6853	Remote Similarity	NPD5763	Approved
0.6842	Remote Similarity	NPD1611	Approved
0.6842	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1091	Approved
0.6838	Remote Similarity	NPD6584	Phase 3
0.6835	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD3020	Approved
0.6832	Remote Similarity	NPD7685	Pre-registration
0.6831	Remote Similarity	NPD2799	Discontinued
0.6822	Remote Similarity	NPD709	Approved
0.6821	Remote Similarity	NPD6386	Approved
0.6821	Remote Similarity	NPD6873	Phase 2
0.6821	Remote Similarity	NPD6385	Approved
0.6818	Remote Similarity	NPD17	Approved
0.6818	Remote Similarity	NPD9381	Approved
0.6818	Remote Similarity	NPD9384	Approved
0.6815	Remote Similarity	NPD196	Phase 1
0.6812	Remote Similarity	NPD9537	Phase 1
0.6812	Remote Similarity	NPD9536	Phase 1
0.6807	Remote Similarity	NPD288	Approved
0.6803	Remote Similarity	NPD5297	Approved
0.6795	Remote Similarity	NPD8127	Discontinued
0.6794	Remote Similarity	NPD1548	Phase 1
0.6786	Remote Similarity	NPD943	Approved
0.6786	Remote Similarity	NPD1240	Approved
0.6783	Remote Similarity	NPD1551	Phase 2
0.6783	Remote Similarity	NPD2161	Phase 2
0.6783	Remote Similarity	NPD6032	Approved
0.6781	Remote Similarity	NPD2354	Approved
0.6777	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD37	Approved
0.6772	Remote Similarity	NPD969	Suspended
0.6769	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3764	Approved
0.6763	Remote Similarity	NPD5718	Phase 2
0.6763	Remote Similarity	NPD3268	Approved
0.6761	Remote Similarity	NPD7097	Phase 1
0.6759	Remote Similarity	NPD4236	Phase 3
0.6759	Remote Similarity	NPD4237	Approved
0.6759	Remote Similarity	NPD4162	Approved
0.6759	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3146	Approved
0.6746	Remote Similarity	NPD5451	Approved
0.6741	Remote Similarity	NPD4359	Approved
0.6741	Remote Similarity	NPD9622	Approved
0.6739	Remote Similarity	NPD2614	Approved
0.6738	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3656	Approved
0.6732	Remote Similarity	NPD2978	Approved
0.6732	Remote Similarity	NPD5563	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