NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.09
Volume:	244.19
LogP:	2.001
LogD:	1.936
LogS:	-2.539
# Rotatable Bonds:	6
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.456
Synthetic Accessibility Score:	2.745
Fsp3:	0.231
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.587
MDCK Permeability:	3.7286885344656184e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.205
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978
Plasma Protein Binding (PPB):	74.49686431884766%
Volume Distribution (VD):	0.416
Pgp-substrate:	44.32486343383789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.334
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.424
CYP2C19-substrate:	0.299
CYP2C9-inhibitor:	0.311
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.308
CYP3A4-inhibitor:	0.174
CYP3A4-substrate:	0.3

ADMET: Excretion

Clearance (CL):	1.301
Half-life (T1/2):	0.695

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.788
AMES Toxicity:	0.973
Rat Oral Acute Toxicity:	0.291
Maximum Recommended Daily Dose:	0.291
Skin Sensitization:	0.14
Carcinogencity:	0.466
Eye Corrosion:	0.007
Eye Irritation:	0.235
Respiratory Toxicity:	0.903

Download Data

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

Natural Product: NPC25067

Natural Product ID:	NPC25067
*Common Name:**	[4-[(1R)-1-Acetyloxyprop-2-Enyl]Phenyl] Acetate
IUPAC Name:	[4-[(1R)-1-acetyloxyprop-2-enyl]phenyl] acetate
Synonyms:
Standard InCHIKey:	JAMQIUWGGBSIKZ-CYBMUJFWSA-N
Standard InCHI:	InChI=1S/C13H14O4/c1-4-13(17-10(3)15)11-5-7-12(8-6-11)16-9(2)14/h4-8,13H,1H2,2-3H3/t13-/m1/s1
SMILES:	C=C[C@H](c1ccc(cc1)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL414656
PubChem CID:	44219741
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002319] Phenol 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
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[12951092]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15930771]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5033	Alpinia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5033	Alpinia galanga	Species	Zingiberaceae	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
Others	12

Activity Type	# Activity
NON-MOLECULAR	5
Organism	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	8200.0	nM	PMID[465106]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	8.4	%	PMID[465107]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	21.2	%	PMID[465107]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	36.8	%	PMID[465107]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	69.2	%	PMID[465107]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4500.0	nM	PMID[465107]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	96.6	%	PMID[465107]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	98.8	%	PMID[465107]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	95.2	%	PMID[465107]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	88.7	%	PMID[465107]
NPT2	Others	Unspecified		Inhibition	=	-5.7	%	PMID[465107]
NPT2	Others	Unspecified		Inhibition	=	4.3	%	PMID[465107]
NPT2	Others	Unspecified		Inhibition	=	0.7	%	PMID[465107]
NPT2	Others	Unspecified		Inhibition	=	11.8	%	PMID[465107]

☑ 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 NPC25067 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	260
0.1-0.2	1497
0.2-0.3	5022
0.3-0.4	12177
0.4-0.5	5914
0.5-0.6	7169
0.6-0.7	8790
0.7-0.8	1759
0.8-0.85	80
0.85-0.9	19
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC231251
1.0	High Similarity	NPC88868
0.9804	High Similarity	NPC291837
0.9439	High Similarity	NPC235250
0.9412	High Similarity	NPC283546
0.932	High Similarity	NPC238115
0.932	High Similarity	NPC473855
0.9216	High Similarity	NPC307425
0.9118	High Similarity	NPC107101
0.9027	High Similarity	NPC267064
0.8952	High Similarity	NPC128730
0.8929	High Similarity	NPC101503
0.8868	High Similarity	NPC176971
0.8796	High Similarity	NPC259554
0.8785	High Similarity	NPC157473
0.8785	High Similarity	NPC151530
0.8774	High Similarity	NPC473393
0.8772	High Similarity	NPC473290
0.8772	High Similarity	NPC471504
0.8762	High Similarity	NPC179686
0.8761	High Similarity	NPC96705
0.8696	High Similarity	NPC163200
0.8684	High Similarity	NPC298796
0.8684	High Similarity	NPC281356
0.8679	High Similarity	NPC109637
0.8649	High Similarity	NPC303522
0.8632	High Similarity	NPC279379
0.8598	High Similarity	NPC8302
0.8596	High Similarity	NPC152306
0.8596	High Similarity	NPC265547
0.8534	High Similarity	NPC180006
0.8534	High Similarity	NPC235190
0.8519	High Similarity	NPC326447
0.8519	High Similarity	NPC1065
0.8509	High Similarity	NPC471498
0.8509	High Similarity	NPC471503
0.8505	High Similarity	NPC38079
0.8505	High Similarity	NPC108875
0.8475	Intermediate Similarity	NPC472518
0.8475	Intermediate Similarity	NPC315807
0.8468	Intermediate Similarity	NPC245552
0.8455	Intermediate Similarity	NPC149545
0.844	Intermediate Similarity	NPC251306
0.8435	Intermediate Similarity	NPC293424
0.8431	Intermediate Similarity	NPC321956
0.843	Intermediate Similarity	NPC199204
0.8426	Intermediate Similarity	NPC470393
0.8421	Intermediate Similarity	NPC128633
0.8417	Intermediate Similarity	NPC234109
0.8417	Intermediate Similarity	NPC188327
0.8411	Intermediate Similarity	NPC305205
0.8403	Intermediate Similarity	NPC201667
0.8403	Intermediate Similarity	NPC73413
0.8393	Intermediate Similarity	NPC115379
0.839	Intermediate Similarity	NPC248429
0.839	Intermediate Similarity	NPC96286
0.8361	Intermediate Similarity	NPC168710
0.8347	Intermediate Similarity	NPC121740
0.8347	Intermediate Similarity	NPC224774
0.8347	Intermediate Similarity	NPC258567
0.8333	Intermediate Similarity	NPC2518
0.8333	Intermediate Similarity	NPC71853
0.8319	Intermediate Similarity	NPC273772
0.8319	Intermediate Similarity	NPC109675
0.8318	Intermediate Similarity	NPC51633
0.8305	Intermediate Similarity	NPC187868
0.8305	Intermediate Similarity	NPC52247
0.8305	Intermediate Similarity	NPC144418
0.8302	Intermediate Similarity	NPC471576
0.8302	Intermediate Similarity	NPC100870
0.8293	Intermediate Similarity	NPC80170
0.8288	Intermediate Similarity	NPC234639
0.8279	Intermediate Similarity	NPC472519
0.8279	Intermediate Similarity	NPC469453
0.8279	Intermediate Similarity	NPC210674
0.8276	Intermediate Similarity	NPC159916
0.8264	Intermediate Similarity	NPC101894
0.8257	Intermediate Similarity	NPC139891
0.825	Intermediate Similarity	NPC27671
0.8241	Intermediate Similarity	NPC192596
0.8241	Intermediate Similarity	NPC298224
0.8235	Intermediate Similarity	NPC69403
0.8235	Intermediate Similarity	NPC8002
0.8235	Intermediate Similarity	NPC99886
0.8235	Intermediate Similarity	NPC291189
0.8235	Intermediate Similarity	NPC177844
0.8235	Intermediate Similarity	NPC259134
0.823	Intermediate Similarity	NPC280760
0.8224	Intermediate Similarity	NPC13755
0.8214	Intermediate Similarity	NPC473809
0.8214	Intermediate Similarity	NPC106141
0.8208	Intermediate Similarity	NPC95755
0.8208	Intermediate Similarity	NPC175298
0.8205	Intermediate Similarity	NPC59561
0.8205	Intermediate Similarity	NPC172253
0.8205	Intermediate Similarity	NPC98748
0.8182	Intermediate Similarity	NPC471827
0.8182	Intermediate Similarity	NPC471828
0.8174	Intermediate Similarity	NPC220540
0.8174	Intermediate Similarity	NPC296526
0.8174	Intermediate Similarity	NPC51345
0.8167	Intermediate Similarity	NPC290605
0.8167	Intermediate Similarity	NPC154176
0.8167	Intermediate Similarity	NPC173350
0.8165	Intermediate Similarity	NPC38209
0.816	Intermediate Similarity	NPC14248
0.816	Intermediate Similarity	NPC194277
0.8158	Intermediate Similarity	NPC301735
0.8145	Intermediate Similarity	NPC79184
0.8145	Intermediate Similarity	NPC307042
0.8145	Intermediate Similarity	NPC113098
0.8145	Intermediate Similarity	NPC476399
0.8142	Intermediate Similarity	NPC233238
0.8131	Intermediate Similarity	NPC171843
0.813	Intermediate Similarity	NPC185066
0.812	Intermediate Similarity	NPC124916
0.8115	Intermediate Similarity	NPC471826
0.8115	Intermediate Similarity	NPC475236
0.8115	Intermediate Similarity	NPC127604
0.8103	Intermediate Similarity	NPC470860
0.8099	Intermediate Similarity	NPC221798
0.8099	Intermediate Similarity	NPC111347
0.8095	Intermediate Similarity	NPC167111
0.8095	Intermediate Similarity	NPC133956
0.8095	Intermediate Similarity	NPC222036
0.8095	Intermediate Similarity	NPC163557
0.8095	Intermediate Similarity	NPC296624
0.8095	Intermediate Similarity	NPC31849
0.8095	Intermediate Similarity	NPC318400
0.8095	Intermediate Similarity	NPC207002
0.8095	Intermediate Similarity	NPC7526
0.8095	Intermediate Similarity	NPC471910
0.8091	Intermediate Similarity	NPC227255
0.8087	Intermediate Similarity	NPC87563
0.8087	Intermediate Similarity	NPC161696
0.8083	Intermediate Similarity	NPC257188
0.8083	Intermediate Similarity	NPC13007
0.808	Intermediate Similarity	NPC272650
0.808	Intermediate Similarity	NPC29734
0.808	Intermediate Similarity	NPC267336
0.808	Intermediate Similarity	NPC250727
0.807	Intermediate Similarity	NPC199462
0.8067	Intermediate Similarity	NPC302107
0.8067	Intermediate Similarity	NPC319378
0.8067	Intermediate Similarity	NPC322569
0.8053	Intermediate Similarity	NPC46844
0.8051	Intermediate Similarity	NPC264976
0.8051	Intermediate Similarity	NPC37858
0.8039	Intermediate Similarity	NPC304760
0.8034	Intermediate Similarity	NPC122117
0.8033	Intermediate Similarity	NPC93219
0.8033	Intermediate Similarity	NPC244495
0.8033	Intermediate Similarity	NPC168259
0.8031	Intermediate Similarity	NPC62366
0.8031	Intermediate Similarity	NPC84894
0.8031	Intermediate Similarity	NPC307412
0.8031	Intermediate Similarity	NPC204353
0.8031	Intermediate Similarity	NPC195343
0.8031	Intermediate Similarity	NPC267412
0.8031	Intermediate Similarity	NPC319859
0.8031	Intermediate Similarity	NPC98179
0.8031	Intermediate Similarity	NPC100986
0.8031	Intermediate Similarity	NPC166672
0.8031	Intermediate Similarity	NPC74655
0.8031	Intermediate Similarity	NPC198381
0.8031	Intermediate Similarity	NPC50896
0.8031	Intermediate Similarity	NPC47163
0.8031	Intermediate Similarity	NPC164269
0.8031	Intermediate Similarity	NPC18804
0.8031	Intermediate Similarity	NPC287182
0.8031	Intermediate Similarity	NPC260265
0.8031	Intermediate Similarity	NPC127888
0.8031	Intermediate Similarity	NPC55149
0.8031	Intermediate Similarity	NPC253574
0.8031	Intermediate Similarity	NPC326600
0.8017	Intermediate Similarity	NPC470887
0.8017	Intermediate Similarity	NPC322358
0.8016	Intermediate Similarity	NPC469956
0.8016	Intermediate Similarity	NPC175159
0.8	Intermediate Similarity	NPC90903
0.8	Intermediate Similarity	NPC109241
0.8	Intermediate Similarity	NPC19242
0.7984	Intermediate Similarity	NPC139595
0.7984	Intermediate Similarity	NPC60704
0.7984	Intermediate Similarity	NPC293642
0.7984	Intermediate Similarity	NPC474623
0.7984	Intermediate Similarity	NPC474651
0.7983	Intermediate Similarity	NPC247553
0.7983	Intermediate Similarity	NPC469708
0.7983	Intermediate Similarity	NPC31314
0.7983	Intermediate Similarity	NPC60589
0.7983	Intermediate Similarity	NPC193193
0.7982	Intermediate Similarity	NPC300166
0.7982	Intermediate Similarity	NPC84325
0.7969	Intermediate Similarity	NPC224941
0.7969	Intermediate Similarity	NPC33986
0.7969	Intermediate Similarity	NPC86892
0.7969	Intermediate Similarity	NPC472424
0.7969	Intermediate Similarity	NPC469675
0.7969	Intermediate Similarity	NPC471625

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 NPC25067 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	978
0.2-0.3	1688
0.3-0.4	2635
0.4-0.5	1759
0.5-0.6	1110
0.6-0.7	593
0.7-0.8	139
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8727	High Similarity	NPD5535	Approved
0.8611	High Similarity	NPD1358	Approved
0.8519	High Similarity	NPD3134	Approved
0.8305	Intermediate Similarity	NPD422	Phase 1
0.8257	Intermediate Similarity	NPD9697	Approved
0.8198	Intermediate Similarity	NPD2684	Approved
0.8158	Intermediate Similarity	NPD1241	Discontinued
0.807	Intermediate Similarity	NPD7843	Approved
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD1778	Approved
0.7983	Intermediate Similarity	NPD17	Approved
0.7966	Intermediate Similarity	NPD1894	Discontinued
0.7946	Intermediate Similarity	NPD290	Approved
0.7917	Intermediate Similarity	NPD3496	Discontinued
0.7913	Intermediate Similarity	NPD821	Approved
0.7899	Intermediate Similarity	NPD5691	Approved
0.7863	Intermediate Similarity	NPD7157	Approved
0.7815	Intermediate Similarity	NPD1548	Phase 1
0.7787	Intermediate Similarity	NPD1608	Approved
0.775	Intermediate Similarity	NPD5585	Approved
0.7717	Intermediate Similarity	NPD1296	Phase 2
0.7717	Intermediate Similarity	NPD6798	Discontinued
0.7705	Intermediate Similarity	NPD1535	Discovery
0.7705	Intermediate Similarity	NPD1611	Approved
0.7699	Intermediate Similarity	NPD968	Approved
0.7674	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5124	Phase 1
0.7674	Intermediate Similarity	NPD4340	Discontinued
0.7669	Intermediate Similarity	NPD1652	Phase 2
0.7667	Intermediate Similarity	NPD9545	Approved
0.7656	Intermediate Similarity	NPD4062	Phase 3
0.7656	Intermediate Similarity	NPD6233	Phase 2
0.7642	Intermediate Similarity	NPD1481	Phase 2
0.7638	Intermediate Similarity	NPD5746	Approved
0.7623	Intermediate Similarity	NPD3847	Discontinued
0.7597	Intermediate Similarity	NPD4140	Approved
0.7581	Intermediate Similarity	NPD3685	Discontinued
0.7578	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1091	Approved
0.7561	Intermediate Similarity	NPD3705	Approved
0.7561	Intermediate Similarity	NPD1610	Phase 2
0.7559	Intermediate Similarity	NPD6832	Phase 2
0.7541	Intermediate Similarity	NPD4626	Approved
0.754	Intermediate Similarity	NPD1019	Discontinued
0.7538	Intermediate Similarity	NPD6355	Discontinued
0.752	Intermediate Similarity	NPD3225	Approved
0.7519	Intermediate Similarity	NPD5745	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD5451	Approved
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD5163	Phase 2
0.75	Intermediate Similarity	NPD3596	Phase 2
0.7481	Intermediate Similarity	NPD4628	Phase 3
0.748	Intermediate Similarity	NPD454	Approved
0.7462	Intermediate Similarity	NPD4060	Phase 1
0.746	Intermediate Similarity	NPD3267	Approved
0.746	Intermediate Similarity	NPD987	Approved
0.746	Intermediate Similarity	NPD6362	Approved
0.746	Intermediate Similarity	NPD3266	Approved
0.744	Intermediate Similarity	NPD4359	Approved
0.7424	Intermediate Similarity	NPD7097	Phase 1
0.7422	Intermediate Similarity	NPD2614	Approved
0.7422	Intermediate Similarity	NPD4908	Phase 1
0.7419	Intermediate Similarity	NPD1281	Approved
0.7407	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD5283	Phase 1
0.7381	Intermediate Similarity	NPD8651	Approved
0.7377	Intermediate Similarity	NPD6581	Approved
0.7377	Intermediate Similarity	NPD6580	Approved
0.7373	Intermediate Similarity	NPD228	Approved
0.7364	Intermediate Similarity	NPD7095	Approved
0.7364	Intermediate Similarity	NPD3179	Approved
0.7364	Intermediate Similarity	NPD3180	Approved
0.7344	Intermediate Similarity	NPD2861	Phase 2
0.7344	Intermediate Similarity	NPD2237	Approved
0.7323	Intermediate Similarity	NPD2797	Approved
0.7317	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD9365	Approved
0.7313	Intermediate Similarity	NPD2240	Approved
0.7313	Intermediate Similarity	NPD2239	Approved
0.7308	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1048	Approved
0.7302	Intermediate Similarity	NPD5327	Phase 3
0.728	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2557	Approved
0.7266	Intermediate Similarity	NPD5647	Approved
0.7259	Intermediate Similarity	NPD6005	Phase 3
0.7259	Intermediate Similarity	NPD6002	Phase 3
0.7259	Intermediate Similarity	NPD6004	Phase 3
0.7259	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5763	Approved
0.7259	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5762	Approved
0.7258	Intermediate Similarity	NPD6516	Phase 2
0.7258	Intermediate Similarity	NPD5846	Approved
0.7252	Intermediate Similarity	NPD8032	Phase 2
0.7252	Intermediate Similarity	NPD4870	Approved
0.7246	Intermediate Similarity	NPD6667	Approved
0.7246	Intermediate Similarity	NPD6666	Approved
0.7244	Intermediate Similarity	NPD1283	Approved
0.7239	Intermediate Similarity	NPD3748	Approved
0.7236	Intermediate Similarity	NPD1182	Approved
0.7234	Intermediate Similarity	NPD3686	Approved
0.7234	Intermediate Similarity	NPD3687	Approved
0.7227	Intermediate Similarity	NPD1137	Approved
0.7227	Intermediate Similarity	NPD1139	Approved
0.7218	Intermediate Similarity	NPD6653	Approved
0.7218	Intermediate Similarity	NPD2653	Approved
0.7214	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1613	Approved
0.7197	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2979	Phase 3
0.7194	Intermediate Similarity	NPD6799	Approved
0.7193	Intermediate Similarity	NPD291	Approved
0.7188	Intermediate Similarity	NPD1819	Approved
0.7188	Intermediate Similarity	NPD1203	Approved
0.7188	Intermediate Similarity	NPD1820	Approved
0.7188	Intermediate Similarity	NPD1818	Approved
0.7188	Intermediate Similarity	NPD1817	Approved
0.7185	Intermediate Similarity	NPD2796	Approved
0.7183	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD1651	Approved
0.7176	Intermediate Similarity	NPD3268	Approved
0.7167	Intermediate Similarity	NPD769	Approved
0.7167	Intermediate Similarity	NPD1138	Approved
0.7165	Intermediate Similarity	NPD2428	Approved
0.7165	Intermediate Similarity	NPD6582	Phase 2
0.7165	Intermediate Similarity	NPD6583	Phase 3
0.7165	Intermediate Similarity	NPD2429	Approved
0.7154	Intermediate Similarity	NPD5536	Phase 2
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3146	Approved
0.7143	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3536	Discontinued
0.7132	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6671	Approved
0.7121	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2556	Approved
0.712	Intermediate Similarity	NPD2554	Approved
0.7109	Intermediate Similarity	NPD196	Phase 1
0.7107	Intermediate Similarity	NPD592	Approved
0.7107	Intermediate Similarity	NPD594	Approved
0.7103	Intermediate Similarity	NPD1282	Approved
0.7101	Intermediate Similarity	NPD4110	Phase 3
0.7101	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3027	Phase 3
0.7092	Intermediate Similarity	NPD2186	Approved
0.7087	Intermediate Similarity	NPD1840	Phase 2
0.708	Intermediate Similarity	NPD4534	Discontinued
0.708	Intermediate Similarity	NPD1549	Phase 2
0.7068	Intermediate Similarity	NPD4307	Phase 2
0.7059	Intermediate Similarity	NPD4477	Approved
0.7059	Intermediate Similarity	NPD2438	Suspended
0.7059	Intermediate Similarity	NPD6032	Approved
0.7059	Intermediate Similarity	NPD4476	Approved
0.7059	Intermediate Similarity	NPD1551	Phase 2
0.705	Intermediate Similarity	NPD3887	Approved
0.7045	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD920	Approved
0.704	Intermediate Similarity	NPD3445	Approved
0.704	Intermediate Similarity	NPD3444	Approved
0.704	Intermediate Similarity	NPD3049	Approved
0.704	Intermediate Similarity	NPD1357	Approved
0.704	Intermediate Similarity	NPD3443	Approved
0.7037	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4536	Approved
0.7037	Intermediate Similarity	NPD4538	Approved
0.7031	Intermediate Similarity	NPD6539	Approved
0.7031	Intermediate Similarity	NPD6540	Phase 3
0.7031	Intermediate Similarity	NPD6542	Approved
0.7031	Intermediate Similarity	NPD6543	Approved
0.7029	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1243	Approved
0.7023	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4622	Approved
0.7015	Intermediate Similarity	NPD4618	Approved
0.7007	Intermediate Similarity	NPD1375	Discontinued
0.7	Intermediate Similarity	NPD3691	Phase 2
0.7	Intermediate Similarity	NPD3690	Phase 2
0.7	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6584	Phase 3
0.6993	Remote Similarity	NPD1653	Approved
0.6985	Remote Similarity	NPD2799	Discontinued
0.6978	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD6538	Approved
0.6977	Remote Similarity	NPD6541	Approved
0.6977	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3167	Approved
0.697	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3165	Approved
0.697	Remote Similarity	NPD3164	Approved
0.697	Remote Similarity	NPD3166	Approved
0.6966	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2934	Approved
0.6964	Remote Similarity	NPD2933	Approved
0.6963	Remote Similarity	NPD3052	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