NPASS Compound

Structure

NPC264976 OpenBabel07101719242D 22 23 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -3.4641 0.0000 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 0.8660 1.5000 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 -2.5981 -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 1.0000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 0.0000 -0.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 14 2 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 15 2 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 16 2 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.1
Volume:	314.204
LogP:	3.33
LogD:	3.241
LogS:	-4.658
# Rotatable Bonds:	7
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.504
Synthetic Accessibility Score:	1.804
Fsp3:	0.111
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.779
MDCK Permeability:	1.5055436961119995e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.085
30% Bioavailability (F30%):	0.57

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.181
Plasma Protein Binding (PPB):	96.47653198242188%
Volume Distribution (VD):	0.533
Pgp-substrate:	0.5259764790534973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.33
CYP1A2-substrate:	0.039
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.594
CYP2C9-substrate:	0.907
CYP2D6-inhibitor:	0.096
CYP2D6-substrate:	0.239
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.122

ADMET: Excretion

Clearance (CL):	1.747
Half-life (T1/2):	0.85

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.844
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.09
Skin Sensitization:	0.965
Carcinogencity:	0.543
Eye Corrosion:	0.034
Eye Irritation:	0.909
Respiratory Toxicity:	0.153

Download Data

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

Natural Product: NPC264976

Natural Product ID:	NPC264976
*Common Name:**	(E)-4-(2,3-Dihydrocinnamoyloxy)Cinnamic Acid
IUPAC Name:	(E)-3-[4-(3-phenylpropanoyloxy)phenyl]prop-2-enoic acid
Synonyms:
Standard InCHIKey:	BPVXGRWWQGNXFW-XYOKQWHBSA-N
Standard InCHI:	InChI=1S/C18H16O4/c19-17(20)12-8-15-6-10-16(11-7-15)22-18(21)13-9-14-4-2-1-3-5-14/h1-8,10-12H,9,13H2,(H,19,20)/b12-8+
SMILES:	O=C(Oc1ccc(cc1)/C=C/C(=O)O)CCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1818958
PubChem CID:	10518022
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0002504] Cinnamic acids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32851	brazilian green propolis	Species	n.a.	n.a.	n.a.	Brazilian green propolis	n.a.	PMID[21865046]

☑ 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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	86.0	%	PMID[488889]
NPT2	Others	Unspecified		Ratio	=	1.08	n.a.	PMID[488889]

☑ 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 NPC264976 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	302
0.1-0.2	1691
0.2-0.3	4494
0.3-0.4	10504
0.4-0.5	7177
0.5-0.6	5136
0.6-0.7	10028
0.7-0.8	3253
0.8-0.85	97
0.85-0.9	12
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC89630
0.9464	High Similarity	NPC51345
0.8898	High Similarity	NPC474874
0.8879	High Similarity	NPC19290
0.877	High Similarity	NPC88403
0.8761	High Similarity	NPC259554
0.8729	High Similarity	NPC293424
0.871	High Similarity	NPC2596
0.864	High Similarity	NPC238309
0.8632	High Similarity	NPC296526
0.8607	High Similarity	NPC473942
0.8571	High Similarity	NPC311091
0.8571	High Similarity	NPC2989
0.8571	High Similarity	NPC471033
0.8559	High Similarity	NPC33717
0.8559	High Similarity	NPC470860
0.8559	High Similarity	NPC128249
0.8548	High Similarity	NPC474476
0.8537	High Similarity	NPC221798
0.8522	High Similarity	NPC183700
0.8492	Intermediate Similarity	NPC241354
0.8487	Intermediate Similarity	NPC263754
0.8487	Intermediate Similarity	NPC183154
0.8462	Intermediate Similarity	NPC223616
0.8448	Intermediate Similarity	NPC233238
0.8438	Intermediate Similarity	NPC307289
0.8435	Intermediate Similarity	NPC234639
0.8435	Intermediate Similarity	NPC79543
0.843	Intermediate Similarity	NPC193193
0.843	Intermediate Similarity	NPC31314
0.8421	Intermediate Similarity	NPC157473
0.8421	Intermediate Similarity	NPC151530
0.8387	Intermediate Similarity	NPC229113
0.8374	Intermediate Similarity	NPC69403
0.8374	Intermediate Similarity	NPC311219
0.8374	Intermediate Similarity	NPC291189
0.8348	Intermediate Similarity	NPC206341
0.8346	Intermediate Similarity	NPC310370
0.8346	Intermediate Similarity	NPC183642
0.8346	Intermediate Similarity	NPC473019
0.8346	Intermediate Similarity	NPC474289
0.8333	Intermediate Similarity	NPC69332
0.8333	Intermediate Similarity	NPC1065
0.8333	Intermediate Similarity	NPC29989
0.8333	Intermediate Similarity	NPC70843
0.8333	Intermediate Similarity	NPC469954
0.8333	Intermediate Similarity	NPC176971
0.8333	Intermediate Similarity	NPC95178
0.8319	Intermediate Similarity	NPC2518
0.8304	Intermediate Similarity	NPC307425
0.8281	Intermediate Similarity	NPC86774
0.8281	Intermediate Similarity	NPC327457
0.8276	Intermediate Similarity	NPC88141
0.8271	Intermediate Similarity	NPC71903
0.8261	Intermediate Similarity	NPC260952
0.8254	Intermediate Similarity	NPC475236
0.8246	Intermediate Similarity	NPC139891
0.8246	Intermediate Similarity	NPC473855
0.8246	Intermediate Similarity	NPC128730
0.8246	Intermediate Similarity	NPC473393
0.824	Intermediate Similarity	NPC107846
0.822	Intermediate Similarity	NPC199462
0.822	Intermediate Similarity	NPC17693
0.8214	Intermediate Similarity	NPC107101
0.8209	Intermediate Similarity	NPC170812
0.8205	Intermediate Similarity	NPC141068
0.8197	Intermediate Similarity	NPC61779
0.8197	Intermediate Similarity	NPC54243
0.8189	Intermediate Similarity	NPC123722
0.8189	Intermediate Similarity	NPC22783
0.8189	Intermediate Similarity	NPC5018
0.8189	Intermediate Similarity	NPC151167
0.8189	Intermediate Similarity	NPC123228
0.8189	Intermediate Similarity	NPC276466
0.8182	Intermediate Similarity	NPC90431
0.8182	Intermediate Similarity	NPC45104
0.8175	Intermediate Similarity	NPC3221
0.8175	Intermediate Similarity	NPC168259
0.8175	Intermediate Similarity	NPC4164
0.8174	Intermediate Similarity	NPC326447
0.816	Intermediate Similarity	NPC14141
0.8158	Intermediate Similarity	NPC283546
0.8158	Intermediate Similarity	NPC109637
0.8151	Intermediate Similarity	NPC109241
0.814	Intermediate Similarity	NPC109778
0.814	Intermediate Similarity	NPC32463
0.813	Intermediate Similarity	NPC230951
0.8125	Intermediate Similarity	NPC2401
0.8125	Intermediate Similarity	NPC226661
0.812	Intermediate Similarity	NPC471068
0.812	Intermediate Similarity	NPC471069
0.8115	Intermediate Similarity	NPC124916
0.8115	Intermediate Similarity	NPC32298
0.811	Intermediate Similarity	NPC120225
0.811	Intermediate Similarity	NPC179777
0.811	Intermediate Similarity	NPC213552
0.811	Intermediate Similarity	NPC84076
0.811	Intermediate Similarity	NPC303680
0.811	Intermediate Similarity	NPC90128
0.8106	Intermediate Similarity	NPC61499
0.8106	Intermediate Similarity	NPC66705
0.8102	Intermediate Similarity	NPC71739
0.8102	Intermediate Similarity	NPC295696
0.8095	Intermediate Similarity	NPC193805
0.8092	Intermediate Similarity	NPC287533
0.8087	Intermediate Similarity	NPC227255
0.8083	Intermediate Similarity	NPC114144
0.8083	Intermediate Similarity	NPC235250
0.8074	Intermediate Similarity	NPC155552
0.807	Intermediate Similarity	NPC298224
0.807	Intermediate Similarity	NPC179686
0.8067	Intermediate Similarity	NPC266116
0.8065	Intermediate Similarity	NPC302107
0.8062	Intermediate Similarity	NPC304622
0.806	Intermediate Similarity	NPC471071
0.806	Intermediate Similarity	NPC327612
0.806	Intermediate Similarity	NPC471072
0.806	Intermediate Similarity	NPC73078
0.806	Intermediate Similarity	NPC284409
0.806	Intermediate Similarity	NPC148738
0.806	Intermediate Similarity	NPC319870
0.806	Intermediate Similarity	NPC471070
0.8051	Intermediate Similarity	NPC231251
0.8051	Intermediate Similarity	NPC88868
0.8051	Intermediate Similarity	NPC25067
0.8051	Intermediate Similarity	NPC473809
0.8049	Intermediate Similarity	NPC98748
0.8049	Intermediate Similarity	NPC35744
0.8049	Intermediate Similarity	NPC37858
0.8047	Intermediate Similarity	NPC243688
0.8047	Intermediate Similarity	NPC161322
0.8047	Intermediate Similarity	NPC224774
0.8047	Intermediate Similarity	NPC258567
0.8047	Intermediate Similarity	NPC37512
0.8047	Intermediate Similarity	NPC121104
0.8047	Intermediate Similarity	NPC142087
0.8047	Intermediate Similarity	NPC95034
0.8047	Intermediate Similarity	NPC121740
0.8045	Intermediate Similarity	NPC246177
0.8045	Intermediate Similarity	NPC317045
0.8034	Intermediate Similarity	NPC31274
0.8034	Intermediate Similarity	NPC291837
0.8033	Intermediate Similarity	NPC240664
0.8031	Intermediate Similarity	NPC280767
0.8031	Intermediate Similarity	NPC137416
0.8031	Intermediate Similarity	NPC2771
0.8031	Intermediate Similarity	NPC289459
0.8029	Intermediate Similarity	NPC17760
0.8029	Intermediate Similarity	NPC473090
0.8029	Intermediate Similarity	NPC160378
0.8017	Intermediate Similarity	NPC220540
0.8017	Intermediate Similarity	NPC23402
0.8017	Intermediate Similarity	NPC188677
0.8017	Intermediate Similarity	NPC113457
0.8016	Intermediate Similarity	NPC93730
0.8016	Intermediate Similarity	NPC315807
0.8	Intermediate Similarity	NPC475102
0.8	Intermediate Similarity	NPC289690
0.8	Intermediate Similarity	NPC8931
0.8	Intermediate Similarity	NPC288452
0.8	Intermediate Similarity	NPC38209
0.8	Intermediate Similarity	NPC187868
0.8	Intermediate Similarity	NPC261573
0.8	Intermediate Similarity	NPC120693
0.8	Intermediate Similarity	NPC469929
0.8	Intermediate Similarity	NPC52247
0.8	Intermediate Similarity	NPC282230
0.8	Intermediate Similarity	NPC183348
0.8	Intermediate Similarity	NPC473988
0.7984	Intermediate Similarity	NPC168050
0.7984	Intermediate Similarity	NPC469453
0.7984	Intermediate Similarity	NPC247553
0.7984	Intermediate Similarity	NPC470092
0.7983	Intermediate Similarity	NPC23332
0.7967	Intermediate Similarity	NPC152306
0.7967	Intermediate Similarity	NPC277460
0.7967	Intermediate Similarity	NPC152159
0.7967	Intermediate Similarity	NPC205502
0.7966	Intermediate Similarity	NPC149545
0.7965	Intermediate Similarity	NPC245561
0.7955	Intermediate Similarity	NPC475468
0.7955	Intermediate Similarity	NPC54503
0.7955	Intermediate Similarity	NPC55147
0.7953	Intermediate Similarity	NPC140521
0.7953	Intermediate Similarity	NPC246704
0.7953	Intermediate Similarity	NPC73413
0.7953	Intermediate Similarity	NPC201667
0.7953	Intermediate Similarity	NPC288945
0.7951	Intermediate Similarity	NPC316062
0.7951	Intermediate Similarity	NPC163398
0.7941	Intermediate Similarity	NPC326065
0.7941	Intermediate Similarity	NPC254994
0.7939	Intermediate Similarity	NPC470976
0.7939	Intermediate Similarity	NPC250727
0.7939	Intermediate Similarity	NPC196979
0.7939	Intermediate Similarity	NPC15083
0.7939	Intermediate Similarity	NPC470977
0.7939	Intermediate Similarity	NPC104854
0.7934	Intermediate Similarity	NPC252004
0.7934	Intermediate Similarity	NPC285350

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 NPC264976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	979
0.2-0.3	1278
0.3-0.4	2473
0.4-0.5	1987
0.5-0.6	1340
0.6-0.7	613
0.7-0.8	183
0.8-0.85	17
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.877	High Similarity	NPD2797	Approved
0.875	High Similarity	NPD1535	Discovery
0.8729	High Similarity	NPD1894	Discontinued
0.8696	High Similarity	NPD5535	Approved
0.8678	High Similarity	NPD1481	Phase 2
0.8618	High Similarity	NPD1203	Approved
0.8571	High Similarity	NPD3268	Approved
0.8462	Intermediate Similarity	NPD1241	Discontinued
0.8413	Intermediate Similarity	NPD2614	Approved
0.8413	Intermediate Similarity	NPD6832	Phase 2
0.8387	Intermediate Similarity	NPD3225	Approved
0.8374	Intermediate Similarity	NPD9717	Approved
0.8321	Intermediate Similarity	NPD2799	Discontinued
0.832	Intermediate Similarity	NPD3266	Approved
0.832	Intermediate Similarity	NPD3267	Approved
0.8281	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8281	Intermediate Similarity	NPD6798	Discontinued
0.8246	Intermediate Similarity	NPD9697	Approved
0.8217	Intermediate Similarity	NPD6233	Phase 2
0.8217	Intermediate Similarity	NPD4062	Phase 3
0.8211	Intermediate Similarity	NPD3847	Discontinued
0.8209	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4308	Phase 3
0.8174	Intermediate Similarity	NPD3134	Approved
0.8148	Intermediate Similarity	NPD4628	Phase 3
0.814	Intermediate Similarity	NPD2313	Discontinued
0.8103	Intermediate Similarity	NPD1358	Approved
0.8092	Intermediate Similarity	NPD6355	Discontinued
0.808	Intermediate Similarity	NPD1608	Approved
0.8029	Intermediate Similarity	NPD7440	Discontinued
0.8015	Intermediate Similarity	NPD4307	Phase 2
0.8015	Intermediate Similarity	NPD3750	Approved
0.8	Intermediate Similarity	NPD422	Phase 1
0.7985	Intermediate Similarity	NPD2935	Discontinued
0.7984	Intermediate Similarity	NPD17	Approved
0.7937	Intermediate Similarity	NPD3972	Approved
0.7923	Intermediate Similarity	NPD7095	Approved
0.792	Intermediate Similarity	NPD3496	Discontinued
0.791	Intermediate Similarity	NPD3748	Approved
0.7903	Intermediate Similarity	NPD5585	Approved
0.7863	Intermediate Similarity	NPD1296	Phase 2
0.7863	Intermediate Similarity	NPD3764	Approved
0.7857	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD6799	Approved
0.7829	Intermediate Similarity	NPD2798	Approved
0.7826	Intermediate Similarity	NPD2354	Approved
0.7823	Intermediate Similarity	NPD9545	Approved
0.782	Intermediate Similarity	NPD4340	Discontinued
0.782	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1283	Approved
0.781	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD8032	Phase 2
0.7794	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD2353	Approved
0.7742	Intermediate Similarity	NPD5536	Phase 2
0.7737	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD2684	Approved
0.773	Intermediate Similarity	NPD6273	Approved
0.7727	Intermediate Similarity	NPD411	Approved
0.7721	Intermediate Similarity	NPD4477	Approved
0.7721	Intermediate Similarity	NPD4476	Approved
0.7721	Intermediate Similarity	NPD1537	Approved
0.7721	Intermediate Similarity	NPD1519	Approved
0.7721	Intermediate Similarity	NPD1551	Phase 2
0.7721	Intermediate Similarity	NPD1538	Phase 1
0.7717	Intermediate Similarity	NPD1281	Approved
0.7712	Intermediate Similarity	NPD968	Approved
0.7704	Intermediate Similarity	NPD1536	Approved
0.7698	Intermediate Similarity	NPD4626	Approved
0.7698	Intermediate Similarity	NPD3887	Approved
0.7692	Intermediate Similarity	NPD1019	Discontinued
0.7692	Intermediate Similarity	NPD5909	Discontinued
0.7687	Intermediate Similarity	NPD1933	Approved
0.7687	Intermediate Similarity	NPD447	Suspended
0.7674	Intermediate Similarity	NPD1876	Approved
0.7664	Intermediate Similarity	NPD2346	Discontinued
0.7664	Intermediate Similarity	NPD2344	Approved
0.7652	Intermediate Similarity	NPD5163	Phase 2
0.7647	Intermediate Similarity	NPD7033	Discontinued
0.7634	Intermediate Similarity	NPD454	Approved
0.7626	Intermediate Similarity	NPD7003	Approved
0.7623	Intermediate Similarity	NPD7843	Approved
0.7619	Intermediate Similarity	NPD1651	Approved
0.7612	Intermediate Similarity	NPD2979	Phase 3
0.7612	Intermediate Similarity	NPD4060	Phase 1
0.7609	Intermediate Similarity	NPD4534	Discontinued
0.7609	Intermediate Similarity	NPD5958	Discontinued
0.7609	Intermediate Similarity	NPD1549	Phase 2
0.7606	Intermediate Similarity	NPD5049	Phase 3
0.7597	Intermediate Similarity	NPD4359	Approved
0.7591	Intermediate Similarity	NPD1522	Approved
0.7591	Intermediate Similarity	NPD1523	Approved
0.7589	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7411	Suspended
0.7574	Intermediate Similarity	NPD1520	Approved
0.7574	Intermediate Similarity	NPD1521	Approved
0.7559	Intermediate Similarity	NPD1778	Approved
0.7557	Intermediate Similarity	NPD5647	Approved
0.7552	Intermediate Similarity	NPD5403	Approved
0.7536	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD9493	Approved
0.7517	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1238	Approved
0.75	Intermediate Similarity	NPD4110	Phase 3
0.7481	Intermediate Similarity	NPD3142	Approved
0.7481	Intermediate Similarity	NPD1240	Approved
0.7481	Intermediate Similarity	NPD3140	Approved
0.748	Intermediate Similarity	NPD5691	Approved
0.7464	Intermediate Similarity	NPD2240	Approved
0.7464	Intermediate Similarity	NPD2796	Approved
0.7464	Intermediate Similarity	NPD2239	Approved
0.7456	Intermediate Similarity	NPD2934	Approved
0.7456	Intermediate Similarity	NPD2933	Approved
0.7448	Intermediate Similarity	NPD3226	Approved
0.7448	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2309	Approved
0.7445	Intermediate Similarity	NPD7097	Phase 1
0.7444	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1611	Approved
0.744	Intermediate Similarity	NPD7157	Approved
0.7426	Intermediate Similarity	NPD4618	Approved
0.7426	Intermediate Similarity	NPD4622	Approved
0.7426	Intermediate Similarity	NPD1184	Approved
0.7422	Intermediate Similarity	NPD5846	Approved
0.7422	Intermediate Similarity	NPD6516	Phase 2
0.7415	Intermediate Similarity	NPD6801	Discontinued
0.7413	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5401	Approved
0.7405	Intermediate Similarity	NPD196	Phase 1
0.7402	Intermediate Similarity	NPD1548	Phase 1
0.7391	Intermediate Similarity	NPD2860	Approved
0.7391	Intermediate Similarity	NPD2859	Approved
0.7391	Intermediate Similarity	NPD1510	Phase 2
0.7383	Intermediate Similarity	NPD7768	Phase 2
0.7379	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD5451	Approved
0.7372	Intermediate Similarity	NPD1607	Approved
0.7365	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7819	Suspended
0.736	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4140	Approved
0.7348	Intermediate Similarity	NPD6362	Approved
0.7339	Intermediate Similarity	NPD821	Approved
0.7338	Intermediate Similarity	NPD2531	Phase 2
0.7338	Intermediate Similarity	NPD2438	Suspended
0.7333	Intermediate Similarity	NPD3749	Approved
0.7333	Intermediate Similarity	NPD7075	Discontinued
0.7329	Intermediate Similarity	NPD7458	Discontinued
0.7328	Intermediate Similarity	NPD6583	Phase 3
0.7328	Intermediate Similarity	NPD6582	Phase 2
0.7319	Intermediate Similarity	NPD5689	Approved
0.7319	Intermediate Similarity	NPD5688	Approved
0.7315	Intermediate Similarity	NPD4288	Approved
0.7305	Intermediate Similarity	NPD1243	Approved
0.7302	Intermediate Similarity	NPD6671	Approved
0.7299	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5124	Phase 1
0.7292	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD5283	Phase 1
0.7279	Intermediate Similarity	NPD4870	Approved
0.7279	Intermediate Similarity	NPD6502	Phase 2
0.7267	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6653	Approved
0.7244	Intermediate Similarity	NPD3596	Phase 2
0.7234	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1511	Approved
0.7219	Intermediate Similarity	NPD6971	Discontinued
0.7218	Intermediate Similarity	NPD1164	Approved
0.7218	Intermediate Similarity	NPD987	Approved
0.7217	Intermediate Similarity	NPD1202	Approved
0.7214	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6032	Approved
0.7213	Intermediate Similarity	NPD9264	Approved
0.7213	Intermediate Similarity	NPD9267	Approved
0.7213	Intermediate Similarity	NPD9263	Approved
0.7206	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3020	Approved
0.72	Intermediate Similarity	NPD3817	Phase 2
0.72	Intermediate Similarity	NPD5402	Approved
0.7192	Intermediate Similarity	NPD8012	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7427	Discontinued
0.7185	Intermediate Similarity	NPD4908	Phase 1
0.7176	Intermediate Similarity	NPD1610	Phase 2
0.7164	Intermediate Similarity	NPD6584	Phase 3
0.7163	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6004	Phase 3
0.7163	Intermediate Similarity	NPD6005	Phase 3
0.7163	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6002	Phase 3
0.7154	Intermediate Similarity	NPD9266	Approved
0.7154	Intermediate Similarity	NPD74	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