NPASS Compound

Structure

NPC471913 OpenBabel07101718182D 28 32 0 0 1 0 0 0 0 0999 V2000 -1.6730 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9319 -0.4824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6049 -0.9306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0591 0.8771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 1.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5708 -0.6718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1566 0.7424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1001 0.8862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 -0.2235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6238 1.1249 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4194 1.3611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8296 0.2941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1533 0.0580 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1225 1.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5791 2.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7956 0.5529 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0802 -0.3173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3813 1.9671 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5138 2.7036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8040 2.9801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 11 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 6 2 0 0 0 0 7 18 1 0 0 0 0 8 11 2 0 0 0 0 8 20 1 0 0 0 0 10 16 2 0 0 0 0 10 19 1 0 0 0 0 12 3 1 6 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 5 1 1 0 0 0 13 21 1 0 0 0 0 14 6 1 1 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 9 1 1 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 9 1 6 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 1 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 23 27 2 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.18
Volume:	391.714
LogP:	3.781
LogD:	3.244
LogS:	-4.368
# Rotatable Bonds:	5
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.404
Synthetic Accessibility Score:	4.276
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.743
MDCK Permeability:	6.006192506902153e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.071
Human Intestinal Absorption (HIA):	0.874
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	98.78141021728516%
Volume Distribution (VD):	0.956
Pgp-substrate:	2.2336347103118896%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.148
CYP2C9-inhibitor:	0.423
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.527
CYP2D6-substrate:	0.71
CYP3A4-inhibitor:	0.126
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	8.191
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.21
Human Hepatotoxicity (H-HT):	0.264
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.237
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.924
Carcinogencity:	0.058
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.851

Download Data

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

Natural Product: NPC471913

Natural Product ID:	NPC471913
*Common Name:**	DWZZUSPCPXZLJI-UPOJXPCUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DWZZUSPCPXZLJI-UPOJXPCUSA-N
Standard InCHI:	InChI=1S/C23H26O5/c24-18-7-4-11(8-20(18)26)2-1-3-12-13-5-6-14-16(23(27)28)10-19(25)17-9-15(12)21(13)22(14)17/h4-8,10,12-15,17,19,21-22,24-26H,1-3,9H2,(H,27,28)/t12-,13-,14+,15+,17+,19-,21-,22+/m1/s1
SMILES:	C1C2C(C=C(C3C2C4C1C(C4C=C3)CCCC5=CC(=C(C=C5)O)O)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3297754
PubChem CID:	90683309
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000135] Catechols

*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
NPO33120	beilschmiedia ferruginea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24901800]

☑ 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
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2796	Individual Protein	Apoptosis regulator Bcl-X	Homo sapiens	Inhibition	=	35.0	%	PMID[528751]
NPT57	Individual Protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	Inhibition	=	7.0	%	PMID[528751]

☑ 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 NPC471913 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	295
0.1-0.2	1169
0.2-0.3	2567
0.3-0.4	6867
0.4-0.5	12569
0.5-0.6	9979
0.6-0.7	8191
0.7-0.8	1034
0.8-0.85	17
0.85-0.9	4
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.937	High Similarity	NPC471935
0.937	High Similarity	NPC471930
0.937	High Similarity	NPC471929
0.9213	High Similarity	NPC471927
0.8531	High Similarity	NPC66894
0.8531	High Similarity	NPC8102
0.8504	High Similarity	NPC471936
0.8504	High Similarity	NPC471925
0.8504	High Similarity	NPC471924
0.8504	High Similarity	NPC471928
0.8489	Intermediate Similarity	NPC471152
0.8438	Intermediate Similarity	NPC471926
0.8403	Intermediate Similarity	NPC189054
0.8385	Intermediate Similarity	NPC470585
0.8345	Intermediate Similarity	NPC43353
0.8333	Intermediate Similarity	NPC471749
0.8333	Intermediate Similarity	NPC86900
0.8322	Intermediate Similarity	NPC469447
0.8322	Intermediate Similarity	NPC477873
0.8309	Intermediate Similarity	NPC30174
0.8286	Intermediate Similarity	NPC476699
0.8252	Intermediate Similarity	NPC35212
0.8209	Intermediate Similarity	NPC15127
0.8207	Intermediate Similarity	NPC53520
0.8194	Intermediate Similarity	NPC235557
0.8194	Intermediate Similarity	NPC310621
0.8194	Intermediate Similarity	NPC252133
0.8189	Intermediate Similarity	NPC306977
0.8189	Intermediate Similarity	NPC242957
0.8189	Intermediate Similarity	NPC206414
0.8189	Intermediate Similarity	NPC287055
0.8182	Intermediate Similarity	NPC473612
0.8182	Intermediate Similarity	NPC323601
0.8138	Intermediate Similarity	NPC26045
0.8133	Intermediate Similarity	NPC105942
0.8133	Intermediate Similarity	NPC205392
0.8106	Intermediate Similarity	NPC265454
0.8106	Intermediate Similarity	NPC34634
0.8099	Intermediate Similarity	NPC476393
0.8095	Intermediate Similarity	NPC472937
0.8095	Intermediate Similarity	NPC472938
0.8095	Intermediate Similarity	NPC472936
0.8092	Intermediate Similarity	NPC63126
0.8082	Intermediate Similarity	NPC271607
0.8082	Intermediate Similarity	NPC280717
0.8077	Intermediate Similarity	NPC299252
0.8077	Intermediate Similarity	NPC277394
0.8077	Intermediate Similarity	NPC61062
0.8074	Intermediate Similarity	NPC288945
0.8071	Intermediate Similarity	NPC18982
0.8071	Intermediate Similarity	NPC475346
0.8071	Intermediate Similarity	NPC475627
0.8071	Intermediate Similarity	NPC475457
0.8069	Intermediate Similarity	NPC471971
0.8069	Intermediate Similarity	NPC30846
0.8069	Intermediate Similarity	NPC469855
0.8069	Intermediate Similarity	NPC471972
0.8056	Intermediate Similarity	NPC27518
0.8056	Intermediate Similarity	NPC82336
0.8056	Intermediate Similarity	NPC78987
0.8056	Intermediate Similarity	NPC304110
0.8042	Intermediate Similarity	NPC182249
0.8042	Intermediate Similarity	NPC248287
0.8042	Intermediate Similarity	NPC318575
0.8042	Intermediate Similarity	NPC234548
0.8031	Intermediate Similarity	NPC222084
0.8014	Intermediate Similarity	NPC477207
0.8	Intermediate Similarity	NPC475454
0.8	Intermediate Similarity	NPC475311
0.8	Intermediate Similarity	NPC118033
0.8	Intermediate Similarity	NPC473680
0.8	Intermediate Similarity	NPC473579
0.7986	Intermediate Similarity	NPC271494
0.7986	Intermediate Similarity	NPC155192
0.7986	Intermediate Similarity	NPC473591
0.7985	Intermediate Similarity	NPC322332
0.7985	Intermediate Similarity	NPC472271
0.7984	Intermediate Similarity	NPC148969
0.7972	Intermediate Similarity	NPC477592
0.7972	Intermediate Similarity	NPC52968
0.7972	Intermediate Similarity	NPC231719
0.7959	Intermediate Similarity	NPC235195
0.7959	Intermediate Similarity	NPC469854
0.7959	Intermediate Similarity	NPC469856
0.7959	Intermediate Similarity	NPC19862
0.7955	Intermediate Similarity	NPC309434
0.7947	Intermediate Similarity	NPC475579
0.7947	Intermediate Similarity	NPC473773
0.7943	Intermediate Similarity	NPC476282
0.7933	Intermediate Similarity	NPC472939
0.7931	Intermediate Similarity	NPC29599
0.7929	Intermediate Similarity	NPC318799
0.7929	Intermediate Similarity	NPC198388
0.7929	Intermediate Similarity	NPC243305
0.7926	Intermediate Similarity	NPC321402
0.7917	Intermediate Similarity	NPC116742
0.7917	Intermediate Similarity	NPC139243
0.791	Intermediate Similarity	NPC98305
0.791	Intermediate Similarity	NPC470848
0.791	Intermediate Similarity	NPC470849
0.7902	Intermediate Similarity	NPC7464
0.7902	Intermediate Similarity	NPC90431
0.7902	Intermediate Similarity	NPC249817
0.7899	Intermediate Similarity	NPC262936
0.7899	Intermediate Similarity	NPC30491
0.7895	Intermediate Similarity	NPC470214
0.7895	Intermediate Similarity	NPC263386
0.7895	Intermediate Similarity	NPC141791
0.7895	Intermediate Similarity	NPC470215
0.7895	Intermediate Similarity	NPC42657
0.7895	Intermediate Similarity	NPC109371
0.7891	Intermediate Similarity	NPC25491
0.7887	Intermediate Similarity	NPC204582
0.7887	Intermediate Similarity	NPC194970
0.7883	Intermediate Similarity	NPC137416
0.7881	Intermediate Similarity	NPC178048
0.7879	Intermediate Similarity	NPC175799
0.7879	Intermediate Similarity	NPC610
0.7879	Intermediate Similarity	NPC200988
0.7879	Intermediate Similarity	NPC145023
0.7879	Intermediate Similarity	NPC278652
0.7872	Intermediate Similarity	NPC25581
0.7872	Intermediate Similarity	NPC5419
0.7872	Intermediate Similarity	NPC61
0.7872	Intermediate Similarity	NPC18074
0.7867	Intermediate Similarity	NPC273358
0.7867	Intermediate Similarity	NPC298647
0.7862	Intermediate Similarity	NPC470616
0.7862	Intermediate Similarity	NPC470617
0.7852	Intermediate Similarity	NPC471970
0.7852	Intermediate Similarity	NPC273798
0.7847	Intermediate Similarity	NPC22676
0.7847	Intermediate Similarity	NPC475482
0.7847	Intermediate Similarity	NPC198621
0.7847	Intermediate Similarity	NPC216940
0.7842	Intermediate Similarity	NPC234175
0.7838	Intermediate Similarity	NPC247221
0.7836	Intermediate Similarity	NPC190501
0.7836	Intermediate Similarity	NPC318552
0.7832	Intermediate Similarity	NPC173569
0.7832	Intermediate Similarity	NPC477874
0.7826	Intermediate Similarity	NPC71610
0.7826	Intermediate Similarity	NPC269598
0.782	Intermediate Similarity	NPC203124
0.782	Intermediate Similarity	NPC86198
0.7817	Intermediate Similarity	NPC155209
0.7817	Intermediate Similarity	NPC168799
0.7815	Intermediate Similarity	NPC142654
0.7815	Intermediate Similarity	NPC470619
0.7815	Intermediate Similarity	NPC470618
0.7815	Intermediate Similarity	NPC208785
0.7815	Intermediate Similarity	NPC145527
0.781	Intermediate Similarity	NPC474766
0.781	Intermediate Similarity	NPC85565
0.7808	Intermediate Similarity	NPC470035
0.7808	Intermediate Similarity	NPC9218
0.7808	Intermediate Similarity	NPC38473
0.7803	Intermediate Similarity	NPC281277
0.78	Intermediate Similarity	NPC96930
0.78	Intermediate Similarity	NPC32017
0.7794	Intermediate Similarity	NPC164947
0.7793	Intermediate Similarity	NPC477849
0.7793	Intermediate Similarity	NPC469857
0.7793	Intermediate Similarity	NPC23667
0.7793	Intermediate Similarity	NPC42384
0.7793	Intermediate Similarity	NPC50615
0.7793	Intermediate Similarity	NPC473779
0.7793	Intermediate Similarity	NPC473479
0.7793	Intermediate Similarity	NPC5014
0.7793	Intermediate Similarity	NPC245760
0.7793	Intermediate Similarity	NPC165191
0.7793	Intermediate Similarity	NPC91887
0.7793	Intermediate Similarity	NPC289358
0.7793	Intermediate Similarity	NPC477593
0.7793	Intermediate Similarity	NPC51531
0.7793	Intermediate Similarity	NPC297797
0.7793	Intermediate Similarity	NPC46242
0.7793	Intermediate Similarity	NPC157284
0.7793	Intermediate Similarity	NPC149773
0.7793	Intermediate Similarity	NPC114333
0.7793	Intermediate Similarity	NPC28592
0.7792	Intermediate Similarity	NPC475484
0.7786	Intermediate Similarity	NPC470747
0.7786	Intermediate Similarity	NPC120280
0.7785	Intermediate Similarity	NPC258856
0.7778	Intermediate Similarity	NPC475216
0.7778	Intermediate Similarity	NPC475595
0.7778	Intermediate Similarity	NPC475145
0.7778	Intermediate Similarity	NPC294361
0.7778	Intermediate Similarity	NPC473544
0.7778	Intermediate Similarity	NPC83663
0.7778	Intermediate Similarity	NPC475162
0.7778	Intermediate Similarity	NPC266084
0.7778	Intermediate Similarity	NPC236520
0.7762	Intermediate Similarity	NPC106406
0.7762	Intermediate Similarity	NPC11266
0.7762	Intermediate Similarity	NPC4982
0.7762	Intermediate Similarity	NPC477594
0.7762	Intermediate Similarity	NPC471110
0.7762	Intermediate Similarity	NPC5310

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 NPC471913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	795
0.2-0.3	1535
0.3-0.4	2737
0.4-0.5	2240
0.5-0.6	1261
0.6-0.7	317
0.7-0.8	21
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8252	Intermediate Similarity	NPD8166	Discontinued
0.797	Intermediate Similarity	NPD2932	Approved
0.7929	Intermediate Similarity	NPD6663	Approved
0.7899	Intermediate Similarity	NPD5736	Approved
0.7836	Intermediate Similarity	NPD3019	Approved
0.7591	Intermediate Similarity	NPD3092	Approved
0.7556	Intermediate Similarity	NPD3091	Approved
0.7538	Intermediate Similarity	NPD3021	Approved
0.7538	Intermediate Similarity	NPD3022	Approved
0.75	Intermediate Similarity	NPD3094	Phase 2
0.7467	Intermediate Similarity	NPD6190	Approved
0.7438	Intermediate Similarity	NPD8127	Discontinued
0.7419	Intermediate Similarity	NPD7028	Phase 2
0.7391	Intermediate Similarity	NPD3023	Approved
0.7391	Intermediate Similarity	NPD3026	Approved
0.7386	Intermediate Similarity	NPD6273	Approved
0.7379	Intermediate Similarity	NPD3620	Phase 2
0.7379	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3025	Approved
0.7372	Intermediate Similarity	NPD3024	Approved
0.7319	Intermediate Similarity	NPD3095	Discontinued
0.7285	Intermediate Similarity	NPD4110	Phase 3
0.7285	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD826	Approved
0.726	Intermediate Similarity	NPD825	Approved
0.7208	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD258	Approved
0.7203	Intermediate Similarity	NPD257	Approved
0.72	Intermediate Similarity	NPD7266	Discontinued
0.7163	Intermediate Similarity	NPD9269	Phase 2
0.7143	Intermediate Similarity	NPD4140	Approved
0.7133	Intermediate Similarity	NPD5408	Approved
0.7133	Intermediate Similarity	NPD5406	Approved
0.7133	Intermediate Similarity	NPD5404	Approved
0.7133	Intermediate Similarity	NPD5405	Approved
0.7124	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3764	Approved
0.7113	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD37	Approved
0.7099	Intermediate Similarity	NPD6234	Discontinued
0.7095	Intermediate Similarity	NPD6355	Discontinued
0.7095	Intermediate Similarity	NPD230	Phase 1
0.7071	Intermediate Similarity	NPD4059	Approved
0.7063	Intermediate Similarity	NPD1283	Approved
0.7059	Intermediate Similarity	NPD4628	Phase 3
0.7034	Intermediate Similarity	NPD9569	Approved
0.7027	Intermediate Similarity	NPD943	Approved
0.7025	Intermediate Similarity	NPD3455	Phase 2
0.702	Intermediate Similarity	NPD9570	Approved
0.7014	Intermediate Similarity	NPD1470	Approved
0.7007	Intermediate Similarity	NPD2629	Approved
0.698	Remote Similarity	NPD555	Phase 2
0.6977	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4966	Approved
0.6975	Remote Similarity	NPD4965	Approved
0.6975	Remote Similarity	NPD4967	Phase 2
0.6974	Remote Similarity	NPD5762	Approved
0.6974	Remote Similarity	NPD5763	Approved
0.6972	Remote Similarity	NPD1201	Approved
0.6968	Remote Similarity	NPD3300	Phase 2
0.6966	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8032	Phase 2
0.6959	Remote Similarity	NPD259	Phase 1
0.6954	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4626	Approved
0.6941	Remote Similarity	NPD7685	Pre-registration
0.6933	Remote Similarity	NPD6653	Approved
0.6923	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD9494	Approved
0.6918	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4060	Phase 1
0.6909	Remote Similarity	NPD7199	Phase 2
0.6908	Remote Similarity	NPD2935	Discontinued
0.6906	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7228	Approved
0.6897	Remote Similarity	NPD1164	Approved
0.6879	Remote Similarity	NPD9268	Approved
0.6871	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD274	Approved
0.6867	Remote Similarity	NPD275	Approved
0.6866	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7236	Approved
0.6853	Remote Similarity	NPD1281	Approved
0.6849	Remote Similarity	NPD5647	Approved
0.6846	Remote Similarity	NPD3020	Approved
0.6842	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7003	Approved
0.6838	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1876	Approved
0.6824	Remote Similarity	NPD9536	Phase 1
0.6824	Remote Similarity	NPD9537	Phase 1
0.6815	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD9545	Approved
0.68	Remote Similarity	NPD2979	Phase 3
0.6797	Remote Similarity	NPD2438	Suspended
0.6779	Remote Similarity	NPD6798	Discontinued
0.6772	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3645	Discontinued
0.6769	Remote Similarity	NPD9495	Approved
0.6765	Remote Similarity	NPD5844	Phase 1
0.6763	Remote Similarity	NPD5951	Approved
0.6761	Remote Similarity	NPD5691	Approved
0.6761	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5735	Approved
0.6748	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3027	Phase 3
0.671	Remote Similarity	NPD5958	Discontinued
0.6708	Remote Similarity	NPD7458	Discontinued
0.6692	Remote Similarity	NPD6647	Phase 2
0.6692	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD228	Approved
0.6647	Remote Similarity	NPD7473	Discontinued
0.6646	Remote Similarity	NPD7239	Suspended
0.6645	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6004	Phase 3
0.6645	Remote Similarity	NPD6005	Phase 3
0.6645	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6002	Phase 3
0.6643	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1651	Approved
0.6624	Remote Similarity	NPD3400	Discontinued
0.6624	Remote Similarity	NPD3750	Approved
0.6623	Remote Similarity	NPD7742	Approved
0.6623	Remote Similarity	NPD7743	Approved
0.6623	Remote Similarity	NPD6233	Phase 2
0.6623	Remote Similarity	NPD2799	Discontinued
0.6623	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4624	Approved
0.662	Remote Similarity	NPD5536	Phase 2
0.6619	Remote Similarity	NPD6858	Approved
0.6619	Remote Similarity	NPD7094	Approved
0.6615	Remote Similarity	NPD2859	Approved
0.6615	Remote Similarity	NPD2860	Approved
0.6608	Remote Similarity	NPD3818	Discontinued
0.66	Remote Similarity	NPD7095	Approved
0.6597	Remote Similarity	NPD9384	Approved
0.6597	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD9381	Approved
0.6596	Remote Similarity	NPD255	Approved
0.6596	Remote Similarity	NPD256	Approved
0.6591	Remote Similarity	NPD2066	Phase 3
0.6589	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1934	Approved
0.6581	Remote Similarity	NPD2531	Phase 2
0.6577	Remote Similarity	NPD2861	Phase 2
0.6571	Remote Similarity	NPD5283	Phase 1
0.6569	Remote Similarity	NPD74	Approved
0.6569	Remote Similarity	NPD9266	Approved
0.6565	Remote Similarity	NPD288	Approved
0.6561	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3268	Approved
0.6554	Remote Similarity	NPD8150	Discontinued
0.6549	Remote Similarity	NPD9493	Approved
0.6543	Remote Similarity	NPD1653	Approved
0.6538	Remote Similarity	NPD2346	Discontinued
0.6538	Remote Similarity	NPD2934	Approved
0.6538	Remote Similarity	NPD2933	Approved
0.6538	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD3657	Discovery
0.6531	Remote Similarity	NPD5327	Phase 3
0.6522	Remote Similarity	NPD4750	Phase 3
0.6519	Remote Similarity	NPD1237	Approved
0.6513	Remote Similarity	NPD4062	Phase 3
0.651	Remote Similarity	NPD6085	Phase 2
0.651	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.65	Remote Similarity	NPD9377	Approved
0.65	Remote Similarity	NPD9379	Approved
0.65	Remote Similarity	NPD7635	Approved
0.6497	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD9264	Approved
0.6496	Remote Similarity	NPD2342	Discontinued
0.6496	Remote Similarity	NPD9267	Approved
0.6496	Remote Similarity	NPD9263	Approved
0.6494	Remote Similarity	NPD6353	Approved
0.6494	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.649	Remote Similarity	NPD7008	Discontinued
0.6489	Remote Similarity	NPD844	Approved
0.6488	Remote Similarity	NPD6315	Phase 2
0.6481	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3062	Approved
0.6471	Remote Similarity	NPD3061	Approved
0.6471	Remote Similarity	NPD1613	Approved
0.6471	Remote Similarity	NPD3059	Approved
0.6467	Remote Similarity	NPD3882	Suspended
0.6463	Remote Similarity	NPD1608	Approved
0.6463	Remote Similarity	NPD4380	Phase 2
0.6461	Remote Similarity	NPD8434	Phase 2
0.646	Remote Similarity	NPD2532	Approved
0.646	Remote Similarity	NPD2534	Approved
0.646	Remote Similarity	NPD2533	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