NPASS Compound

Structure

NPC471924 OpenBabel07101719152D 26 30 0 0 1 0 0 0 0 0999 V2000 2.6730 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3801 -1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6049 0.0694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0532 -1.6037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0580 3.1533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5708 0.3282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0191 -1.3449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8862 3.1001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8771 0.0591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3778 0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 1.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3461 -0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2779 -0.3789 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 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1249 1.6238 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3611 2.4194 0.0000 C 0 0 2 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 -0.3090 1.9511 0.0000 C 0 0 2 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 -2.3482 2.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2438 -0.1201 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7036 3.5138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9801 1.8040 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 13 1 0 0 0 0 4 7 1 0 0 0 0 4 13 2 0 0 0 0 5 8 2 0 0 0 0 5 13 1 0 0 0 0 6 9 2 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 19 1 0 0 0 0 10 11 2 0 0 0 0 12 14 1 0 0 0 0 14 6 1 6 0 0 0 14 21 1 0 0 0 0 15 24 1 0 0 0 0 16 3 1 6 0 0 0 16 17 1 0 0 0 0 16 20 1 0 0 0 0 17 10 1 1 0 0 0 17 22 1 0 0 0 0 18 11 1 1 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 23 1 6 0 0 0 20 12 1 1 0 0 0 20 22 1 0 0 0 0 21 22 1 0 0 0 0 23 25 2 0 0 0 0 23 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.19
Volume:	374.134
LogP:	5.482
LogD:	4.687
LogS:	-3.356
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.772
Synthetic Accessibility Score:	4.53
Fsp3:	0.522
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:	-4.956
MDCK Permeability:	1.3064583072264213e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.116
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.482
Plasma Protein Binding (PPB):	96.0905532836914%
Volume Distribution (VD):	0.231
Pgp-substrate:	3.4485063552856445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.563
CYP1A2-substrate:	0.233
CYP2C19-inhibitor:	0.33
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.703
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.278
CYP2D6-substrate:	0.606
CYP3A4-inhibitor:	0.483
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	5.684
Half-life (T1/2):	0.886

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.726
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.912
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.928
Carcinogencity:	0.41
Eye Corrosion:	0.043
Eye Irritation:	0.534
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC471924

Natural Product ID:	NPC471924
*Common Name:**	CUBPKSUGCMULEZ-UWQNPUKESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CUBPKSUGCMULEZ-UWQNPUKESA-N
Standard InCHI:	InChI=1S/C23H26O3/c24-15-7-4-13(5-8-15)2-1-3-16-17-10-11-18-19(23(25)26)9-6-14-12-20(16)22(17)21(14)18/h4-11,14,16-22,24H,1-3,12H2,(H,25,26)/t14-,16-,17-,18+,19-,20+,21-,22-/m1/s1
SMILES:	OC(=O)[C@@H]1C=C[C@H]2[C@@H]3[C@H]1C=C[C@H]1[C@@H]3[C@@H](C2)[C@@H]1CCCc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3298851
PubChem CID:	90645494
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
Ki	1
Others	2

Activity Type	# Activity
Individual Protein	3

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	=	22.0	%	PMID[520379]
NPT2796	Individual Protein	Apoptosis regulator Bcl-X	Homo sapiens	Ki	>	100000.0	nM	PMID[520379]
NPT57	Individual Protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	Inhibition	=	0.0	%	PMID[520379]

☑ 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 NPC471924 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	280
0.1-0.2	1305
0.2-0.3	2793
0.3-0.4	8817
0.4-0.5	11535
0.5-0.6	12725
0.6-0.7	4823
0.7-0.8	392
0.8-0.85	17
0.85-0.9	2
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471928
1.0	High Similarity	NPC471925
0.9908	High Similarity	NPC471926
0.9231	High Similarity	NPC471927
0.9076	High Similarity	NPC471929
0.9076	High Similarity	NPC471935
0.9076	High Similarity	NPC471930
0.8947	High Similarity	NPC471936
0.8519	High Similarity	NPC245561
0.8504	High Similarity	NPC471913
0.844	Intermediate Similarity	NPC52472
0.8403	Intermediate Similarity	NPC31296
0.8403	Intermediate Similarity	NPC473974
0.8403	Intermediate Similarity	NPC258366
0.8403	Intermediate Similarity	NPC79933
0.8403	Intermediate Similarity	NPC42657
0.8378	Intermediate Similarity	NPC120693
0.8378	Intermediate Similarity	NPC261573
0.8378	Intermediate Similarity	NPC8931
0.8333	Intermediate Similarity	NPC318552
0.8333	Intermediate Similarity	NPC190501
0.8246	Intermediate Similarity	NPC31274
0.8235	Intermediate Similarity	NPC325295
0.8235	Intermediate Similarity	NPC76308
0.823	Intermediate Similarity	NPC188677
0.8158	Intermediate Similarity	NPC228737
0.8142	Intermediate Similarity	NPC13495
0.812	Intermediate Similarity	NPC286222
0.8115	Intermediate Similarity	NPC164852
0.8115	Intermediate Similarity	NPC241001
0.8091	Intermediate Similarity	NPC260000
0.807	Intermediate Similarity	NPC95178
0.807	Intermediate Similarity	NPC70843
0.807	Intermediate Similarity	NPC29989
0.807	Intermediate Similarity	NPC69332
0.8067	Intermediate Similarity	NPC322197
0.8049	Intermediate Similarity	NPC162935
0.8049	Intermediate Similarity	NPC249340
0.8033	Intermediate Similarity	NPC478121
0.8033	Intermediate Similarity	NPC470585
0.803	Intermediate Similarity	NPC52968
0.803	Intermediate Similarity	NPC231719
0.8018	Intermediate Similarity	NPC280869
0.8017	Intermediate Similarity	NPC328694
0.8017	Intermediate Similarity	NPC88141
0.8	Intermediate Similarity	NPC216520
0.8	Intermediate Similarity	NPC292730
0.8	Intermediate Similarity	NPC325646
0.8	Intermediate Similarity	NPC82664
0.8	Intermediate Similarity	NPC28951
0.8	Intermediate Similarity	NPC132271
0.7984	Intermediate Similarity	NPC121168
0.7967	Intermediate Similarity	NPC32322
0.7967	Intermediate Similarity	NPC259703
0.7966	Intermediate Similarity	NPC17693
0.7966	Intermediate Similarity	NPC242957
0.7966	Intermediate Similarity	NPC287055
0.7966	Intermediate Similarity	NPC206414
0.7966	Intermediate Similarity	NPC306977
0.7965	Intermediate Similarity	NPC13426
0.7949	Intermediate Similarity	NPC222084
0.7949	Intermediate Similarity	NPC21162
0.7949	Intermediate Similarity	NPC252544
0.7949	Intermediate Similarity	NPC321252
0.7939	Intermediate Similarity	NPC477594
0.7937	Intermediate Similarity	NPC137416
0.7931	Intermediate Similarity	NPC317305
0.7913	Intermediate Similarity	NPC317592
0.7899	Intermediate Similarity	NPC109241
0.7881	Intermediate Similarity	NPC177576
0.7879	Intermediate Similarity	NPC477596
0.7874	Intermediate Similarity	NPC269598
0.7863	Intermediate Similarity	NPC326187
0.7857	Intermediate Similarity	NPC7435
0.7857	Intermediate Similarity	NPC15127
0.7852	Intermediate Similarity	NPC323601
0.7851	Intermediate Similarity	NPC128249
0.7838	Intermediate Similarity	NPC473388
0.7833	Intermediate Similarity	NPC221870
0.7829	Intermediate Similarity	NPC117899
0.7818	Intermediate Similarity	NPC151715
0.7812	Intermediate Similarity	NPC30491
0.7812	Intermediate Similarity	NPC262936
0.7807	Intermediate Similarity	NPC135784
0.7798	Intermediate Similarity	NPC304541
0.7761	Intermediate Similarity	NPC477592
0.776	Intermediate Similarity	NPC154696
0.7752	Intermediate Similarity	NPC193203
0.7752	Intermediate Similarity	NPC229894
0.775	Intermediate Similarity	NPC148969
0.7748	Intermediate Similarity	NPC26244
0.7739	Intermediate Similarity	NPC254965
0.7739	Intermediate Similarity	NPC327811
0.7731	Intermediate Similarity	NPC322753
0.7724	Intermediate Similarity	NPC161943
0.7724	Intermediate Similarity	NPC471033
0.7724	Intermediate Similarity	NPC311091
0.7724	Intermediate Similarity	NPC474890
0.7724	Intermediate Similarity	NPC273282
0.7719	Intermediate Similarity	NPC472585
0.7717	Intermediate Similarity	NPC474766
0.7712	Intermediate Similarity	NPC95172
0.771	Intermediate Similarity	NPC18798
0.7704	Intermediate Similarity	NPC248287
0.7704	Intermediate Similarity	NPC234548
0.7704	Intermediate Similarity	NPC477593
0.7699	Intermediate Similarity	NPC92730
0.7698	Intermediate Similarity	NPC68167
0.7698	Intermediate Similarity	NPC189054
0.7686	Intermediate Similarity	NPC285350
0.768	Intermediate Similarity	NPC474175
0.768	Intermediate Similarity	NPC21216
0.7679	Intermediate Similarity	NPC202986
0.7672	Intermediate Similarity	NPC303141
0.7672	Intermediate Similarity	NPC243677
0.7667	Intermediate Similarity	NPC48525
0.7661	Intermediate Similarity	NPC182240
0.7661	Intermediate Similarity	NPC233165
0.7661	Intermediate Similarity	NPC184579
0.7658	Intermediate Similarity	NPC81010
0.7658	Intermediate Similarity	NPC27323
0.7658	Intermediate Similarity	NPC32977
0.7658	Intermediate Similarity	NPC316301
0.7652	Intermediate Similarity	NPC470202
0.7652	Intermediate Similarity	NPC168829
0.7647	Intermediate Similarity	NPC296683
0.7647	Intermediate Similarity	NPC116842
0.7647	Intermediate Similarity	NPC63345
0.7647	Intermediate Similarity	NPC222905
0.7642	Intermediate Similarity	NPC160199
0.7638	Intermediate Similarity	NPC174991
0.7638	Intermediate Similarity	NPC236981
0.7638	Intermediate Similarity	NPC14141
0.7636	Intermediate Similarity	NPC45040
0.7627	Intermediate Similarity	NPC11554
0.7627	Intermediate Similarity	NPC470039
0.7623	Intermediate Similarity	NPC23402
0.7623	Intermediate Similarity	NPC51345
0.7623	Intermediate Similarity	NPC4665
0.7619	Intermediate Similarity	NPC472271
0.7619	Intermediate Similarity	NPC253627
0.7615	Intermediate Similarity	NPC318325
0.7615	Intermediate Similarity	NPC478147
0.7615	Intermediate Similarity	NPC258219
0.7615	Intermediate Similarity	NPC123273
0.7615	Intermediate Similarity	NPC280347
0.7615	Intermediate Similarity	NPC242240
0.7615	Intermediate Similarity	NPC177420
0.7611	Intermediate Similarity	NPC77492
0.7611	Intermediate Similarity	NPC225464
0.7607	Intermediate Similarity	NPC271274
0.7603	Intermediate Similarity	NPC309808
0.76	Intermediate Similarity	NPC473136
0.7594	Intermediate Similarity	NPC18982
0.7594	Intermediate Similarity	NPC475627
0.7594	Intermediate Similarity	NPC475457
0.7594	Intermediate Similarity	NPC475346
0.7589	Intermediate Similarity	NPC274678
0.7586	Intermediate Similarity	NPC288411
0.7583	Intermediate Similarity	NPC228609
0.7581	Intermediate Similarity	NPC104514
0.7578	Intermediate Similarity	NPC199273
0.7576	Intermediate Similarity	NPC125153
0.7563	Intermediate Similarity	NPC234639
0.7563	Intermediate Similarity	NPC79543
0.7561	Intermediate Similarity	NPC474387
0.7561	Intermediate Similarity	NPC247858
0.7561	Intermediate Similarity	NPC257540
0.7561	Intermediate Similarity	NPC299252
0.7561	Intermediate Similarity	NPC137496
0.7561	Intermediate Similarity	NPC83718
0.7561	Intermediate Similarity	NPC154511
0.7561	Intermediate Similarity	NPC61062
0.7561	Intermediate Similarity	NPC474358
0.7561	Intermediate Similarity	NPC277394
0.7559	Intermediate Similarity	NPC11250
0.7559	Intermediate Similarity	NPC176208
0.7559	Intermediate Similarity	NPC244351
0.7559	Intermediate Similarity	NPC469927
0.7559	Intermediate Similarity	NPC283514
0.7559	Intermediate Similarity	NPC164947
0.7557	Intermediate Similarity	NPC131684
0.7554	Intermediate Similarity	NPC477207
0.7545	Intermediate Similarity	NPC192
0.7545	Intermediate Similarity	NPC55561
0.7544	Intermediate Similarity	NPC78119
0.7544	Intermediate Similarity	NPC132078
0.7544	Intermediate Similarity	NPC51333
0.7544	Intermediate Similarity	NPC216468
0.7542	Intermediate Similarity	NPC29883
0.7542	Intermediate Similarity	NPC226699
0.754	Intermediate Similarity	NPC272454
0.754	Intermediate Similarity	NPC190971
0.754	Intermediate Similarity	NPC301987
0.754	Intermediate Similarity	NPC179092
0.754	Intermediate Similarity	NPC159760
0.754	Intermediate Similarity	NPC35856
0.754	Intermediate Similarity	NPC26433
0.754	Intermediate Similarity	NPC222876
0.754	Intermediate Similarity	NPC292665

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 NPC471924 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	853
0.2-0.3	1253
0.3-0.4	2762
0.4-0.5	2366
0.5-0.6	1273
0.6-0.7	356
0.7-0.8	24
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8487	Intermediate Similarity	NPD2932	Approved
0.8333	Intermediate Similarity	NPD3019	Approved
0.8018	Intermediate Similarity	NPD3020	Approved
0.7984	Intermediate Similarity	NPD6663	Approved
0.7953	Intermediate Similarity	NPD5736	Approved
0.7748	Intermediate Similarity	NPD2859	Approved
0.7748	Intermediate Similarity	NPD2860	Approved
0.768	Intermediate Similarity	NPD3026	Approved
0.768	Intermediate Similarity	NPD3023	Approved
0.7661	Intermediate Similarity	NPD3024	Approved
0.7661	Intermediate Similarity	NPD3025	Approved
0.7658	Intermediate Similarity	NPD2933	Approved
0.7658	Intermediate Similarity	NPD2934	Approved
0.7658	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD255	Approved
0.7623	Intermediate Similarity	NPD256	Approved
0.7542	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3764	Approved
0.746	Intermediate Similarity	NPD4059	Approved
0.744	Intermediate Similarity	NPD3091	Approved
0.7419	Intermediate Similarity	NPD9568	Approved
0.7417	Intermediate Similarity	NPD3022	Approved
0.7417	Intermediate Similarity	NPD3021	Approved
0.7385	Intermediate Similarity	NPD2797	Approved
0.7385	Intermediate Similarity	NPD1164	Approved
0.7345	Intermediate Similarity	NPD1693	Approved
0.7333	Intermediate Similarity	NPD6355	Discontinued
0.7313	Intermediate Similarity	NPD8032	Phase 2
0.7308	Intermediate Similarity	NPD1283	Approved
0.7257	Intermediate Similarity	NPD845	Approved
0.7257	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD288	Approved
0.7209	Intermediate Similarity	NPD1535	Discovery
0.7209	Intermediate Similarity	NPD3092	Approved
0.719	Intermediate Similarity	NPD74	Approved
0.719	Intermediate Similarity	NPD9266	Approved
0.7177	Intermediate Similarity	NPD2234	Approved
0.7177	Intermediate Similarity	NPD2229	Approved
0.7177	Intermediate Similarity	NPD2228	Approved
0.7176	Intermediate Similarity	NPD1876	Approved
0.7165	Intermediate Similarity	NPD1759	Phase 1
0.7165	Intermediate Similarity	NPD9545	Approved
0.7165	Intermediate Similarity	NPD1894	Discontinued
0.7163	Intermediate Similarity	NPD8166	Discontinued
0.7156	Intermediate Similarity	NPD111	Approved
0.7154	Intermediate Similarity	NPD1608	Approved
0.7154	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1086	Approved
0.7143	Intermediate Similarity	NPD1090	Approved
0.7143	Intermediate Similarity	NPD5909	Discontinued
0.7143	Intermediate Similarity	NPD1089	Approved
0.7132	Intermediate Similarity	NPD3847	Discontinued
0.7131	Intermediate Similarity	NPD4750	Phase 3
0.713	Intermediate Similarity	NPD1809	Phase 2
0.713	Intermediate Similarity	NPD844	Approved
0.7119	Intermediate Similarity	NPD846	Approved
0.7119	Intermediate Similarity	NPD940	Approved
0.7111	Intermediate Similarity	NPD3268	Approved
0.7109	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD9264	Approved
0.7107	Intermediate Similarity	NPD9263	Approved
0.7107	Intermediate Similarity	NPD9267	Approved
0.7094	Intermediate Similarity	NPD2066	Phase 3
0.709	Intermediate Similarity	NPD2614	Approved
0.7087	Intermediate Similarity	NPD1758	Phase 1
0.7077	Intermediate Similarity	NPD1281	Approved
0.7077	Intermediate Similarity	NPD1201	Approved
0.7068	Intermediate Similarity	NPD258	Approved
0.7068	Intermediate Similarity	NPD257	Approved
0.7059	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD800	Approved
0.7054	Intermediate Similarity	NPD3095	Discontinued
0.7049	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5958	Discontinued
0.7018	Intermediate Similarity	NPD1088	Approved
0.7009	Intermediate Similarity	NPD9495	Approved
0.7008	Intermediate Similarity	NPD9493	Approved
0.7007	Intermediate Similarity	NPD4140	Approved
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3094	Phase 2
0.6985	Remote Similarity	NPD6798	Discontinued
0.6984	Remote Similarity	NPD5951	Approved
0.6984	Remote Similarity	NPD2629	Approved
0.6972	Remote Similarity	NPD9491	Approved
0.697	Remote Similarity	NPD1755	Approved
0.696	Remote Similarity	NPD5535	Approved
0.6944	Remote Similarity	NPD226	Approved
0.694	Remote Similarity	NPD5647	Approved
0.694	Remote Similarity	NPD2798	Approved
0.693	Remote Similarity	NPD1239	Approved
0.6929	Remote Similarity	NPD2799	Discontinued
0.6929	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4626	Approved
0.6923	Remote Similarity	NPD17	Approved
0.6923	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3750	Approved
0.6923	Remote Similarity	NPD4110	Phase 3
0.6923	Remote Similarity	NPD7003	Approved
0.6918	Remote Similarity	NPD6273	Approved
0.6917	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1929	Approved
0.6917	Remote Similarity	NPD1930	Approved
0.6912	Remote Similarity	NPD7095	Approved
0.6903	Remote Similarity	NPD5347	Phase 2
0.6903	Remote Similarity	NPD5346	Phase 2
0.6897	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD1242	Phase 1
0.6889	Remote Similarity	NPD9569	Approved
0.6889	Remote Similarity	NPD2861	Phase 2
0.6885	Remote Similarity	NPD1445	Approved
0.6885	Remote Similarity	NPD1444	Approved
0.6884	Remote Similarity	NPD825	Approved
0.6884	Remote Similarity	NPD826	Approved
0.6879	Remote Similarity	NPD2935	Discontinued
0.6875	Remote Similarity	NPD1087	Approved
0.6875	Remote Similarity	NPD4793	Discontinued
0.6866	Remote Similarity	NPD1470	Approved
0.6855	Remote Similarity	NPD1792	Phase 2
0.6846	Remote Similarity	NPD4093	Discontinued
0.6846	Remote Similarity	NPD1651	Approved
0.6846	Remote Similarity	NPD7028	Phase 2
0.6842	Remote Similarity	NPD9256	Approved
0.6842	Remote Similarity	NPD9258	Approved
0.6831	Remote Similarity	NPD6004	Phase 3
0.6831	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD6005	Phase 3
0.6831	Remote Similarity	NPD6002	Phase 3
0.6829	Remote Similarity	NPD2342	Discontinued
0.6825	Remote Similarity	NPD7635	Approved
0.6815	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4624	Approved
0.6812	Remote Similarity	NPD6233	Phase 2
0.6806	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3400	Discontinued
0.6794	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3136	Phase 2
0.6786	Remote Similarity	NPD6653	Approved
0.678	Remote Similarity	NPD1564	Approved
0.678	Remote Similarity	NPD1565	Approved
0.678	Remote Similarity	NPD1566	Phase 3
0.6777	Remote Similarity	NPD9261	Approved
0.6777	Remote Similarity	NPD5765	Approved
0.6772	Remote Similarity	NPD1241	Discontinued
0.6763	Remote Similarity	NPD2979	Phase 3
0.6763	Remote Similarity	NPD4060	Phase 1
0.6761	Remote Similarity	NPD4476	Approved
0.6761	Remote Similarity	NPD4477	Approved
0.675	Remote Similarity	NPD3028	Approved
0.6748	Remote Similarity	NPD3134	Approved
0.6741	Remote Similarity	NPD3266	Approved
0.6741	Remote Similarity	NPD3267	Approved
0.6741	Remote Similarity	NPD6362	Approved
0.6739	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD9281	Approved
0.6718	Remote Similarity	NPD5585	Approved
0.6714	Remote Similarity	NPD274	Approved
0.6714	Remote Similarity	NPD275	Approved
0.6691	Remote Similarity	NPD6085	Phase 2
0.6691	Remote Similarity	NPD259	Phase 1
0.6691	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD4062	Phase 3
0.669	Remote Similarity	NPD7033	Discontinued
0.669	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD4534	Discontinued
0.6667	Remote Similarity	NPD227	Approved
0.6667	Remote Similarity	NPD225	Approved
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5305	Approved
0.6667	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD196	Phase 1
0.6667	Remote Similarity	NPD5306	Approved
0.6667	Remote Similarity	NPD2286	Discontinued
0.6667	Remote Similarity	NPD9536	Phase 1
0.6667	Remote Similarity	NPD9537	Phase 1
0.6643	Remote Similarity	NPD6346	Approved
0.6642	Remote Similarity	NPD9269	Phase 2
0.6642	Remote Similarity	NPD3972	Approved
0.6641	Remote Similarity	NPD5303	Approved
0.6641	Remote Similarity	NPD5304	Approved
0.6639	Remote Similarity	NPD6647	Phase 2
0.6621	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD2313	Discontinued
0.6618	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD1203	Approved
0.6618	Remote Similarity	NPD987	Approved
0.6614	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6685	Approved
0.6606	Remote Similarity	NPD9490	Approved
0.66	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD3300	Phase 2
0.6597	Remote Similarity	NPD2344	Approved
0.6596	Remote Similarity	NPD555	Phase 2

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