NPASS Compound

Structure

CID182119 OpenBabel06191715562D 34 36 0 0 1 0 0 0 0 0999 V2000 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 2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -6.0000 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 -0.0000 -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 -5.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 0.8660 -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 -1.7321 -2.0000 0.0000 C 0 0 2 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 32 1 0 0 0 0 2 33 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 17 2 0 0 0 0 13 21 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 29 1 0 0 0 0 23 26 1 0 0 0 0 24 25 2 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 26 20 1 1 0 0 0 26 34 1 0 0 0 0 27 29 2 3 0 0 0 27 30 1 0 0 0 0 28 31 2 0 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	457.19
Volume:	487.849
LogP:	4.161
LogD:	3.794
LogS:	-5.607
# Rotatable Bonds:	12
TPSA:	73.86
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.349
Synthetic Accessibility Score:	2.762
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.946
MDCK Permeability:	1.2542659533210099e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.084
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.921

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.393
Plasma Protein Binding (PPB):	98.25372314453125%
Volume Distribution (VD):	0.517
Pgp-substrate:	1.533537745475769%

ADMET: Metabolism

CYP1A2-inhibitor:	0.375
CYP1A2-substrate:	0.178
CYP2C19-inhibitor:	0.968
CYP2C19-substrate:	0.246
CYP2C9-inhibitor:	0.959
CYP2C9-substrate:	0.975
CYP2D6-inhibitor:	0.445
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.926
CYP3A4-substrate:	0.409

ADMET: Excretion

Clearance (CL):	6.557
Half-life (T1/2):	0.275

ADMET: Toxicity

hERG Blockers:	0.532
Human Hepatotoxicity (H-HT):	0.674
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.876
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.085
Skin Sensitization:	0.951
Carcinogencity:	0.451
Eye Corrosion:	0.004
Eye Irritation:	0.088
Respiratory Toxicity:	0.566

Download Data

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

Natural Product: NPC182119

Natural Product ID:	NPC182119
*Common Name:**	Syncarpamide
IUPAC Name:	[(1S)-1-(3,4-dimethoxyphenyl)-2-[[(E)-3-phenylprop-2-enoyl]amino]ethyl] (E)-3-phenylprop-2-enoate
Synonyms:	Syncarpamide
Standard InCHIKey:	CUXXAUBWEIJETF-AMVLLGRPSA-N
Standard InCHI:	InChI=1S/C28H27NO5/c1-32-24-16-15-23(19-25(24)33-2)26(34-28(31)18-14-22-11-7-4-8-12-22)20-29-27(30)17-13-21-9-5-3-6-10-21/h3-19,26H,20H2,1-2H3,(H,29,30)/b17-13+,18-14+/t26-/m1/s1
SMILES:	COc1cc(ccc1OC)[C@H](OC(=O)/C=C/c1ccccc1)CN=C(/C=C/c1ccccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458478
PubChem CID:	11753871
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0003480] Cinnamic acid esters

*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
NPO27680	Zanthoxylum syncarpum	Species	Rutaceae	Eukaryota	n.a.	stem	n.a.	PMID[14738394]
NPO27680	Zanthoxylum syncarpum	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16124784]
NPO27680	Zanthoxylum syncarpum	Species	Rutaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2040.0	nM	PMID[484699]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3060.0	nM	PMID[484699]

☑ 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 NPC182119 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	194
0.1-0.2	1109
0.2-0.3	4362
0.3-0.4	11991
0.4-0.5	5423
0.5-0.6	8270
0.6-0.7	9837
0.7-0.8	1467
0.8-0.85	38
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC299583
0.8658	High Similarity	NPC277857
0.8658	High Similarity	NPC115144
0.86	High Similarity	NPC471032
0.86	High Similarity	NPC470935
0.8552	High Similarity	NPC312770
0.8552	High Similarity	NPC41473
0.8552	High Similarity	NPC14600
0.8552	High Similarity	NPC160607
0.8552	High Similarity	NPC204848
0.85	High Similarity	NPC301713
0.8366	Intermediate Similarity	NPC478189
0.8333	Intermediate Similarity	NPC214869
0.8286	Intermediate Similarity	NPC211218
0.8194	Intermediate Similarity	NPC35961
0.8194	Intermediate Similarity	NPC52029
0.8194	Intermediate Similarity	NPC195749
0.8163	Intermediate Similarity	NPC135127
0.8158	Intermediate Similarity	NPC5462
0.8146	Intermediate Similarity	NPC178466
0.8146	Intermediate Similarity	NPC67467
0.8146	Intermediate Similarity	NPC63628
0.8138	Intermediate Similarity	NPC114102
0.8125	Intermediate Similarity	NPC155838
0.8121	Intermediate Similarity	NPC126206
0.8121	Intermediate Similarity	NPC296898
0.8099	Intermediate Similarity	NPC95733
0.8099	Intermediate Similarity	NPC62101
0.8095	Intermediate Similarity	NPC282477
0.8095	Intermediate Similarity	NPC284855
0.8056	Intermediate Similarity	NPC251571
0.8056	Intermediate Similarity	NPC153990
0.8054	Intermediate Similarity	NPC471664
0.8054	Intermediate Similarity	NPC254610
0.8054	Intermediate Similarity	NPC471665
0.8039	Intermediate Similarity	NPC313414
0.8028	Intermediate Similarity	NPC279379
0.8012	Intermediate Similarity	NPC50380
0.8012	Intermediate Similarity	NPC179250
0.7987	Intermediate Similarity	NPC143120
0.7987	Intermediate Similarity	NPC473909
0.7987	Intermediate Similarity	NPC274960
0.7986	Intermediate Similarity	NPC120225
0.7986	Intermediate Similarity	NPC213552
0.7962	Intermediate Similarity	NPC127402
0.7961	Intermediate Similarity	NPC222039
0.7961	Intermediate Similarity	NPC100478
0.7939	Intermediate Similarity	NPC474953
0.7933	Intermediate Similarity	NPC120852
0.7931	Intermediate Similarity	NPC186898
0.7917	Intermediate Similarity	NPC29477
0.7917	Intermediate Similarity	NPC289459
0.7908	Intermediate Similarity	NPC140502
0.7888	Intermediate Similarity	NPC329640
0.7885	Intermediate Similarity	NPC153644
0.7866	Intermediate Similarity	NPC329717
0.7866	Intermediate Similarity	NPC90984
0.7857	Intermediate Similarity	NPC277460
0.7847	Intermediate Similarity	NPC246704
0.7834	Intermediate Similarity	NPC102934
0.7834	Intermediate Similarity	NPC252402
0.7823	Intermediate Similarity	NPC83062
0.7812	Intermediate Similarity	NPC107602
0.7806	Intermediate Similarity	NPC160378
0.78	Intermediate Similarity	NPC119060
0.78	Intermediate Similarity	NPC249791
0.78	Intermediate Similarity	NPC476387
0.78	Intermediate Similarity	NPC237594
0.78	Intermediate Similarity	NPC67247
0.78	Intermediate Similarity	NPC309744
0.7785	Intermediate Similarity	NPC475250
0.7785	Intermediate Similarity	NPC5423
0.7778	Intermediate Similarity	NPC288452
0.7778	Intermediate Similarity	NPC289690
0.7778	Intermediate Similarity	NPC110699
0.7778	Intermediate Similarity	NPC106055
0.7765	Intermediate Similarity	NPC475794
0.7758	Intermediate Similarity	NPC474858
0.7756	Intermediate Similarity	NPC252292
0.7756	Intermediate Similarity	NPC100998
0.7756	Intermediate Similarity	NPC476382
0.7756	Intermediate Similarity	NPC34587
0.7756	Intermediate Similarity	NPC132771
0.7756	Intermediate Similarity	NPC34927
0.7755	Intermediate Similarity	NPC210674
0.775	Intermediate Similarity	NPC18249
0.775	Intermediate Similarity	NPC305700
0.775	Intermediate Similarity	NPC197741
0.775	Intermediate Similarity	NPC140915
0.775	Intermediate Similarity	NPC187028
0.775	Intermediate Similarity	NPC10221
0.775	Intermediate Similarity	NPC56635
0.7748	Intermediate Similarity	NPC214729
0.7746	Intermediate Similarity	NPC263835
0.7742	Intermediate Similarity	NPC478239
0.7724	Intermediate Similarity	NPC109822
0.7724	Intermediate Similarity	NPC20443
0.7724	Intermediate Similarity	NPC146886
0.7724	Intermediate Similarity	NPC60517
0.7724	Intermediate Similarity	NPC94276
0.7718	Intermediate Similarity	NPC93882
0.7718	Intermediate Similarity	NPC130595
0.7707	Intermediate Similarity	NPC40222
0.7707	Intermediate Similarity	NPC268515
0.7706	Intermediate Similarity	NPC329816
0.7703	Intermediate Similarity	NPC470706
0.7697	Intermediate Similarity	NPC471988
0.7697	Intermediate Similarity	NPC471719
0.7692	Intermediate Similarity	NPC473090
0.7692	Intermediate Similarity	NPC267064
0.7688	Intermediate Similarity	NPC243891
0.7688	Intermediate Similarity	NPC300329
0.7688	Intermediate Similarity	NPC275027
0.7687	Intermediate Similarity	NPC99798
0.7687	Intermediate Similarity	NPC157740
0.7677	Intermediate Similarity	NPC157816
0.7676	Intermediate Similarity	NPC37858
0.7674	Intermediate Similarity	NPC474650
0.7667	Intermediate Similarity	NPC313737
0.7667	Intermediate Similarity	NPC285078
0.7667	Intermediate Similarity	NPC245120
0.7667	Intermediate Similarity	NPC6854
0.766	Intermediate Similarity	NPC280001
0.7658	Intermediate Similarity	NPC476347
0.7658	Intermediate Similarity	NPC232992
0.7651	Intermediate Similarity	NPC329595
0.7651	Intermediate Similarity	NPC476399
0.7651	Intermediate Similarity	NPC79184
0.7651	Intermediate Similarity	NPC307042
0.7651	Intermediate Similarity	NPC326599
0.7647	Intermediate Similarity	NPC281780
0.7647	Intermediate Similarity	NPC241704
0.7643	Intermediate Similarity	NPC163898
0.764	Intermediate Similarity	NPC120774
0.764	Intermediate Similarity	NPC163598
0.764	Intermediate Similarity	NPC264875
0.764	Intermediate Similarity	NPC267091
0.764	Intermediate Similarity	NPC478268
0.764	Intermediate Similarity	NPC476434
0.764	Intermediate Similarity	NPC212699
0.764	Intermediate Similarity	NPC207675
0.7639	Intermediate Similarity	NPC147654
0.7635	Intermediate Similarity	NPC246974
0.7635	Intermediate Similarity	NPC110313
0.7635	Intermediate Similarity	NPC474178
0.7635	Intermediate Similarity	NPC245826
0.7635	Intermediate Similarity	NPC147247
0.7635	Intermediate Similarity	NPC252307
0.7625	Intermediate Similarity	NPC474560
0.7625	Intermediate Similarity	NPC221091
0.7625	Intermediate Similarity	NPC259576
0.7619	Intermediate Similarity	NPC191037
0.7619	Intermediate Similarity	NPC178284
0.7619	Intermediate Similarity	NPC156944
0.7619	Intermediate Similarity	NPC251466
0.7619	Intermediate Similarity	NPC58607
0.7616	Intermediate Similarity	NPC218530
0.7616	Intermediate Similarity	NPC473463
0.7616	Intermediate Similarity	NPC474607
0.7613	Intermediate Similarity	NPC186406
0.7613	Intermediate Similarity	NPC224876
0.7613	Intermediate Similarity	NPC83375
0.761	Intermediate Similarity	NPC476348
0.761	Intermediate Similarity	NPC192763
0.761	Intermediate Similarity	NPC201148
0.761	Intermediate Similarity	NPC215095
0.761	Intermediate Similarity	NPC199311
0.761	Intermediate Similarity	NPC261122
0.761	Intermediate Similarity	NPC210611
0.761	Intermediate Similarity	NPC28651
0.761	Intermediate Similarity	NPC80732
0.761	Intermediate Similarity	NPC3460
0.761	Intermediate Similarity	NPC187398
0.761	Intermediate Similarity	NPC300262
0.7597	Intermediate Similarity	NPC77572
0.7597	Intermediate Similarity	NPC477837
0.7597	Intermediate Similarity	NPC477838
0.7595	Intermediate Similarity	NPC199928
0.7593	Intermediate Similarity	NPC115203
0.7593	Intermediate Similarity	NPC475141
0.7586	Intermediate Similarity	NPC71090
0.7586	Intermediate Similarity	NPC288238
0.7584	Intermediate Similarity	NPC5851
0.7584	Intermediate Similarity	NPC86030
0.7582	Intermediate Similarity	NPC157554
0.7582	Intermediate Similarity	NPC37468
0.758	Intermediate Similarity	NPC232228
0.758	Intermediate Similarity	NPC110063
0.7578	Intermediate Similarity	NPC58661
0.7578	Intermediate Similarity	NPC270811
0.7578	Intermediate Similarity	NPC471073
0.7571	Intermediate Similarity	NPC294941
0.7569	Intermediate Similarity	NPC204466
0.7569	Intermediate Similarity	NPC471877
0.7569	Intermediate Similarity	NPC470848
0.7569	Intermediate Similarity	NPC470849
0.7568	Intermediate Similarity	NPC194841
0.7568	Intermediate Similarity	NPC319625
0.7568	Intermediate Similarity	NPC163332
0.7568	Intermediate Similarity	NPC147821

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 NPC182119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	605
0.2-0.3	1071
0.3-0.4	2209
0.4-0.5	2395
0.5-0.6	1691
0.6-0.7	906
0.7-0.8	129
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8289	Intermediate Similarity	NPD4123	Phase 3
0.8067	Intermediate Similarity	NPD1375	Discontinued
0.8038	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD4678	Approved
0.8025	Intermediate Similarity	NPD4675	Approved
0.8024	Intermediate Similarity	NPD7038	Approved
0.8024	Intermediate Similarity	NPD7039	Approved
0.8013	Intermediate Similarity	NPD3687	Approved
0.8013	Intermediate Similarity	NPD3686	Approved
0.7908	Intermediate Similarity	NPD6331	Phase 2
0.7908	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6385	Approved
0.7862	Intermediate Similarity	NPD6386	Approved
0.7843	Intermediate Similarity	NPD3060	Approved
0.784	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD5773	Approved
0.7764	Intermediate Similarity	NPD5772	Approved
0.7736	Intermediate Similarity	NPD4005	Discontinued
0.7727	Intermediate Similarity	NPD4237	Approved
0.7727	Intermediate Similarity	NPD4236	Phase 3
0.7718	Intermediate Similarity	NPD2674	Phase 3
0.7662	Intermediate Similarity	NPD7153	Discontinued
0.7654	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2161	Phase 2
0.7643	Intermediate Similarity	NPD4357	Discontinued
0.7635	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD5241	Discontinued
0.7625	Intermediate Similarity	NPD3455	Phase 2
0.7613	Intermediate Similarity	NPD4162	Approved
0.7595	Intermediate Similarity	NPD4739	Approved
0.758	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7549	Discontinued
0.7548	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3145	Approved
0.7533	Intermediate Similarity	NPD3144	Approved
0.7532	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6746	Phase 2
0.7516	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5242	Approved
0.75	Intermediate Similarity	NPD6584	Phase 3
0.7484	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4210	Discontinued
0.7451	Intermediate Similarity	NPD2653	Approved
0.7439	Intermediate Similarity	NPD2977	Approved
0.7439	Intermediate Similarity	NPD2978	Approved
0.7438	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7526	Approved
0.7438	Intermediate Similarity	NPD52	Approved
0.7423	Intermediate Similarity	NPD5090	Approved
0.7423	Intermediate Similarity	NPD5089	Approved
0.7419	Intermediate Similarity	NPD6032	Approved
0.7417	Intermediate Similarity	NPD5718	Phase 2
0.7415	Intermediate Similarity	NPD1669	Approved
0.7391	Intermediate Similarity	NPD2122	Discontinued
0.7381	Intermediate Similarity	NPD2821	Approved
0.7375	Intermediate Similarity	NPD3536	Discontinued
0.7372	Intermediate Similarity	NPD7266	Discontinued
0.7372	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2922	Phase 1
0.7351	Intermediate Similarity	NPD3027	Phase 3
0.7345	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5677	Discontinued
0.732	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1048	Approved
0.7297	Intermediate Similarity	NPD6583	Phase 3
0.7297	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6582	Phase 2
0.7297	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2219	Phase 1
0.7292	Intermediate Similarity	NPD5536	Phase 2
0.7289	Intermediate Similarity	NPD5353	Approved
0.7278	Intermediate Similarity	NPD5177	Phase 3
0.7267	Intermediate Similarity	NPD3146	Approved
0.7267	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3656	Approved
0.7256	Intermediate Similarity	NPD6502	Phase 2
0.7255	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7477	Discontinued
0.7255	Intermediate Similarity	NPD840	Approved
0.7255	Intermediate Similarity	NPD839	Approved
0.7244	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4108	Discontinued
0.7244	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6873	Phase 2
0.7208	Intermediate Similarity	NPD1558	Phase 1
0.7202	Intermediate Similarity	NPD6971	Discontinued
0.7202	Intermediate Similarity	NPD4055	Discovery
0.7202	Intermediate Similarity	NPD5604	Discontinued
0.7179	Intermediate Similarity	NPD6895	Approved
0.7179	Intermediate Similarity	NPD6896	Approved
0.717	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5709	Phase 3
0.7151	Intermediate Similarity	NPD4481	Phase 3
0.7143	Intermediate Similarity	NPD3531	Approved
0.7143	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7124	Phase 2
0.7143	Intermediate Similarity	NPD6667	Approved
0.7143	Intermediate Similarity	NPD3532	Approved
0.7143	Intermediate Similarity	NPD6666	Approved
0.7143	Intermediate Similarity	NPD3530	Approved
0.7133	Intermediate Similarity	NPD5283	Phase 1
0.7125	Intermediate Similarity	NPD4110	Phase 3
0.7125	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6580	Approved
0.7123	Intermediate Similarity	NPD6581	Approved
0.7118	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD4666	Phase 3
0.7117	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3052	Approved
0.7115	Intermediate Similarity	NPD3054	Approved
0.7108	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3274	Phase 2
0.7107	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4993	Discontinued
0.7099	Intermediate Similarity	NPD7212	Phase 2
0.7099	Intermediate Similarity	NPD7213	Phase 3
0.7097	Intermediate Similarity	NPD3061	Approved
0.7097	Intermediate Similarity	NPD3062	Approved
0.7097	Intermediate Similarity	NPD3059	Approved
0.7097	Intermediate Similarity	NPD2238	Phase 2
0.7091	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6190	Approved
0.7078	Intermediate Similarity	NPD5109	Approved
0.7078	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5111	Phase 2
0.7078	Intermediate Similarity	NPD5110	Phase 2
0.7075	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1358	Approved
0.7067	Intermediate Similarity	NPD3685	Discontinued
0.7062	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6843	Phase 3
0.7056	Intermediate Similarity	NPD6842	Approved
0.7056	Intermediate Similarity	NPD6841	Approved
0.7055	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7447	Phase 1
0.7051	Intermediate Similarity	NPD4340	Discontinued
0.7047	Intermediate Similarity	NPD3705	Approved
0.7045	Intermediate Similarity	NPD7007	Discovery
0.7041	Intermediate Similarity	NPD7773	Phase 2
0.7035	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6233	Phase 2
0.7032	Intermediate Similarity	NPD5745	Approved
0.703	Intermediate Similarity	NPD1653	Approved
0.7029	Intermediate Similarity	NPD5844	Phase 1
0.702	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4628	Phase 3
0.7006	Intermediate Similarity	NPD5314	Approved
0.7006	Intermediate Similarity	NPD2492	Phase 1
0.7006	Intermediate Similarity	NPD6072	Discontinued
0.7	Intermediate Similarity	NPD2231	Phase 2
0.7	Intermediate Similarity	NPD2235	Phase 2
0.6994	Remote Similarity	NPD4083	Discontinued
0.6989	Remote Similarity	NPD5557	Phase 1
0.6988	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1613	Approved
0.6987	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD3817	Phase 2
0.6982	Remote Similarity	NPD2563	Approved
0.6982	Remote Similarity	NPD2560	Approved
0.698	Remote Similarity	NPD3496	Discontinued
0.6977	Remote Similarity	NPD8127	Discontinued
0.6977	Remote Similarity	NPD6107	Approved
0.6975	Remote Similarity	NPD3692	Discontinued
0.6975	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2677	Approved
0.6971	Remote Similarity	NPD7177	Discontinued
0.6971	Remote Similarity	NPD3909	Discontinued
0.697	Remote Similarity	NPD6031	Approved
0.697	Remote Similarity	NPD5976	Discontinued
0.697	Remote Similarity	NPD6030	Approved
0.6968	Remote Similarity	NPD6798	Discontinued
0.6964	Remote Similarity	NPD4433	Discontinued
0.6964	Remote Similarity	NPD37	Approved
0.6957	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3823	Discontinued
0.6944	Remote Similarity	NPD5535	Approved
0.6943	Remote Similarity	NPD555	Phase 2
0.6941	Remote Similarity	NPD4966	Approved
0.6941	Remote Similarity	NPD4967	Phase 2
0.6941	Remote Similarity	NPD4965	Approved
0.6936	Remote Similarity	NPD7315	Approved
0.6936	Remote Similarity	NPD3051	Approved
0.6935	Remote Similarity	NPD4420	Approved
0.6932	Remote Similarity	NPD5095	Phase 3
0.6932	Remote Similarity	NPD5096	Phase 3
0.6923	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD9384	Approved
0.6913	Remote Similarity	NPD2667	Approved
0.6913	Remote Similarity	NPD2668	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