NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.16
Volume:	286.824
LogP:	3.021
LogD:	2.678
LogS:	-3.651
# Rotatable Bonds:	0
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	3.939
Fsp3:	0.647
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:	-4.587
MDCK Permeability:	2.6177762265433557e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.212
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.598
Plasma Protein Binding (PPB):	83.30542755126953%
Volume Distribution (VD):	2.017
Pgp-substrate:	8.34805965423584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.358
CYP1A2-substrate:	0.458
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.707
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.083
CYP3A4-substrate:	0.334

ADMET: Excretion

Clearance (CL):	12.949
Half-life (T1/2):	0.476

ADMET: Toxicity

hERG Blockers:	0.167
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.086
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.951
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.937
Carcinogencity:	0.858
Eye Corrosion:	0.035
Eye Irritation:	0.585
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC475166

Natural Product ID:	NPC475166
*Common Name:**	13-Beta-Hydroxyestradiol
IUPAC Name:	(8R,9S,13R,14S,17S)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,13,17-triol
Synonyms:	13-Beta-Hydroxyestradiol
Standard InCHIKey:	OKPUBHQTELTBJD-UHDSXZAQSA-N
Standard InCHI:	InChI=1S/C17H22O3/c18-11-2-4-12-10(9-11)1-3-14-13(12)7-8-17(20)15(14)5-6-16(17)19/h2,4,9,13-16,18-20H,1,3,5-8H2/t13-,14-,15+,16+,17-/m1/s1
SMILES:	C1CC(C2(C1C3CCC4=C(C3CC2)C=CC(=C4)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499812
PubChem CID:	44566760
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003236] 17-hydroxysteroids

*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
NPO27821.1	Pochonia chlamydosporia	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12828470]

☑ 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
EC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	EC50	=	19.0	nM	PMID[528519]

☑ 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 NPC475166 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	369
0.1-0.2	1285
0.2-0.3	2967
0.3-0.4	8143
0.4-0.5	11423
0.5-0.6	11053
0.6-0.7	6430
0.7-0.8	968
0.8-0.85	43
0.85-0.9	9
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC142198
0.9487	High Similarity	NPC77569
0.9402	High Similarity	NPC328504
0.9145	High Similarity	NPC164649
0.9145	High Similarity	NPC48342
0.8992	High Similarity	NPC68339
0.8926	High Similarity	NPC321402
0.8667	High Similarity	NPC469609
0.8667	High Similarity	NPC471671
0.8655	High Similarity	NPC474387
0.8655	High Similarity	NPC474358
0.8655	High Similarity	NPC257540
0.8655	High Similarity	NPC137496
0.8655	High Similarity	NPC154511
0.8655	High Similarity	NPC247858
0.8618	High Similarity	NPC471794
0.8595	High Similarity	NPC469644
0.8583	High Similarity	NPC304510
0.8583	High Similarity	NPC172219
0.8571	High Similarity	NPC147179
0.8547	High Similarity	NPC322753
0.8525	High Similarity	NPC99734
0.85	High Similarity	NPC308311
0.85	High Similarity	NPC219112
0.85	High Similarity	NPC308828
0.85	High Similarity	NPC38893
0.85	High Similarity	NPC477137
0.8487	Intermediate Similarity	NPC268160
0.8448	Intermediate Similarity	NPC11554
0.843	Intermediate Similarity	NPC477136
0.8417	Intermediate Similarity	NPC35797
0.8417	Intermediate Similarity	NPC192948
0.8361	Intermediate Similarity	NPC154030
0.8347	Intermediate Similarity	NPC92
0.8347	Intermediate Similarity	NPC469663
0.8333	Intermediate Similarity	NPC120280
0.8281	Intermediate Similarity	NPC30491
0.8281	Intermediate Similarity	NPC471077
0.8281	Intermediate Similarity	NPC262936
0.8264	Intermediate Similarity	NPC474486
0.8264	Intermediate Similarity	NPC469719
0.8244	Intermediate Similarity	NPC321502
0.8235	Intermediate Similarity	NPC95716
0.8197	Intermediate Similarity	NPC141001
0.8182	Intermediate Similarity	NPC471534
0.8182	Intermediate Similarity	NPC473137
0.8182	Intermediate Similarity	NPC12656
0.8175	Intermediate Similarity	NPC71094
0.8167	Intermediate Similarity	NPC46940
0.8167	Intermediate Similarity	NPC228425
0.8151	Intermediate Similarity	NPC141782
0.8151	Intermediate Similarity	NPC132720
0.8151	Intermediate Similarity	NPC44732
0.8145	Intermediate Similarity	NPC151197
0.813	Intermediate Similarity	NPC16030
0.8125	Intermediate Similarity	NPC124030
0.8125	Intermediate Similarity	NPC87985
0.8099	Intermediate Similarity	NPC715
0.8099	Intermediate Similarity	NPC471485
0.8083	Intermediate Similarity	NPC260323
0.8083	Intermediate Similarity	NPC176279
0.8083	Intermediate Similarity	NPC308689
0.8083	Intermediate Similarity	NPC151537
0.808	Intermediate Similarity	NPC260832
0.808	Intermediate Similarity	NPC223451
0.808	Intermediate Similarity	NPC190501
0.808	Intermediate Similarity	NPC135467
0.808	Intermediate Similarity	NPC318552
0.8067	Intermediate Similarity	NPC55617
0.8067	Intermediate Similarity	NPC62258
0.8062	Intermediate Similarity	NPC470724
0.8062	Intermediate Similarity	NPC145659
0.8062	Intermediate Similarity	NPC9292
0.8062	Intermediate Similarity	NPC269598
0.8051	Intermediate Similarity	NPC151477
0.8049	Intermediate Similarity	NPC471668
0.8033	Intermediate Similarity	NPC195922
0.8031	Intermediate Similarity	NPC120172
0.8017	Intermediate Similarity	NPC250323
0.8017	Intermediate Similarity	NPC473521
0.8	Intermediate Similarity	NPC147634
0.8	Intermediate Similarity	NPC294741
0.8	Intermediate Similarity	NPC174096
0.8	Intermediate Similarity	NPC120982
0.8	Intermediate Similarity	NPC476536
0.8	Intermediate Similarity	NPC176893
0.8	Intermediate Similarity	NPC79793
0.8	Intermediate Similarity	NPC13482
0.8	Intermediate Similarity	NPC226401
0.7985	Intermediate Similarity	NPC311256
0.7984	Intermediate Similarity	NPC470726
0.7983	Intermediate Similarity	NPC149455
0.7983	Intermediate Similarity	NPC472982
0.7983	Intermediate Similarity	NPC64642
0.7983	Intermediate Similarity	NPC262365
0.7967	Intermediate Similarity	NPC84999
0.7967	Intermediate Similarity	NPC246760
0.7956	Intermediate Similarity	NPC164743
0.7951	Intermediate Similarity	NPC317869
0.7949	Intermediate Similarity	NPC254965
0.7949	Intermediate Similarity	NPC327811
0.7949	Intermediate Similarity	NPC323810
0.7934	Intermediate Similarity	NPC187583
0.7934	Intermediate Similarity	NPC179002
0.7934	Intermediate Similarity	NPC77772
0.7934	Intermediate Similarity	NPC257430
0.7923	Intermediate Similarity	NPC325294
0.7923	Intermediate Similarity	NPC321822
0.792	Intermediate Similarity	NPC206
0.7917	Intermediate Similarity	NPC58865
0.7917	Intermediate Similarity	NPC314187
0.7917	Intermediate Similarity	NPC473524
0.7913	Intermediate Similarity	NPC132078
0.7913	Intermediate Similarity	NPC78119
0.7913	Intermediate Similarity	NPC51333
0.7913	Intermediate Similarity	NPC216468
0.7907	Intermediate Similarity	NPC181334
0.7907	Intermediate Similarity	NPC97578
0.7907	Intermediate Similarity	NPC15127
0.7903	Intermediate Similarity	NPC472862
0.7899	Intermediate Similarity	NPC472979
0.7899	Intermediate Similarity	NPC27252
0.7895	Intermediate Similarity	NPC78575
0.7895	Intermediate Similarity	NPC238168
0.7895	Intermediate Similarity	NPC237424
0.7895	Intermediate Similarity	NPC312341
0.7895	Intermediate Similarity	NPC202986
0.7886	Intermediate Similarity	NPC107240
0.7881	Intermediate Similarity	NPC471350
0.7881	Intermediate Similarity	NPC117115
0.7869	Intermediate Similarity	NPC471179
0.7857	Intermediate Similarity	NPC93071
0.7857	Intermediate Similarity	NPC126002
0.7857	Intermediate Similarity	NPC477207
0.7852	Intermediate Similarity	NPC471942
0.7845	Intermediate Similarity	NPC213730
0.784	Intermediate Similarity	NPC299180
0.784	Intermediate Similarity	NPC320864
0.7833	Intermediate Similarity	NPC306295
0.7829	Intermediate Similarity	NPC198014
0.7829	Intermediate Similarity	NPC471187
0.7829	Intermediate Similarity	NPC473451
0.782	Intermediate Similarity	NPC470727
0.7815	Intermediate Similarity	NPC271274
0.7815	Intermediate Similarity	NPC21594
0.7812	Intermediate Similarity	NPC474115
0.7812	Intermediate Similarity	NPC253627
0.7805	Intermediate Similarity	NPC319803
0.7805	Intermediate Similarity	NPC322239
0.7805	Intermediate Similarity	NPC176730
0.7805	Intermediate Similarity	NPC123175
0.7803	Intermediate Similarity	NPC307050
0.7803	Intermediate Similarity	NPC311293
0.7803	Intermediate Similarity	NPC148366
0.7803	Intermediate Similarity	NPC277458
0.7797	Intermediate Similarity	NPC12278
0.7797	Intermediate Similarity	NPC475225
0.7797	Intermediate Similarity	NPC315794
0.7795	Intermediate Similarity	NPC472071
0.7787	Intermediate Similarity	NPC266937
0.7787	Intermediate Similarity	NPC469912
0.7787	Intermediate Similarity	NPC470770
0.7787	Intermediate Similarity	NPC111108
0.7787	Intermediate Similarity	NPC54373
0.7786	Intermediate Similarity	NPC43000
0.7786	Intermediate Similarity	NPC100414
0.7778	Intermediate Similarity	NPC471578
0.7778	Intermediate Similarity	NPC7686
0.7778	Intermediate Similarity	NPC40258
0.7778	Intermediate Similarity	NPC91461
0.7778	Intermediate Similarity	NPC227719
0.7778	Intermediate Similarity	NPC101025
0.7769	Intermediate Similarity	NPC228343
0.7769	Intermediate Similarity	NPC254833
0.7769	Intermediate Similarity	NPC224342
0.7752	Intermediate Similarity	NPC478058
0.7752	Intermediate Similarity	NPC152946
0.7752	Intermediate Similarity	NPC11250
0.775	Intermediate Similarity	NPC472980
0.775	Intermediate Similarity	NPC66834
0.7744	Intermediate Similarity	NPC288290
0.7742	Intermediate Similarity	NPC249270
0.7739	Intermediate Similarity	NPC292730
0.7739	Intermediate Similarity	NPC216520
0.7739	Intermediate Similarity	NPC82664
0.7739	Intermediate Similarity	NPC132271
0.7737	Intermediate Similarity	NPC476699
0.7734	Intermediate Similarity	NPC470414
0.7731	Intermediate Similarity	NPC471133
0.7731	Intermediate Similarity	NPC243601
0.7731	Intermediate Similarity	NPC239291
0.7727	Intermediate Similarity	NPC108164
0.7727	Intermediate Similarity	NPC186889
0.7724	Intermediate Similarity	NPC62867
0.7724	Intermediate Similarity	NPC302371
0.7724	Intermediate Similarity	NPC177962
0.7717	Intermediate Similarity	NPC42657
0.7717	Intermediate Similarity	NPC473974
0.7717	Intermediate Similarity	NPC258366
0.7717	Intermediate Similarity	NPC323074

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 NPC475166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	807
0.2-0.3	1370
0.3-0.4	2957
0.4-0.5	2112
0.5-0.6	1215
0.6-0.7	337
0.7-0.8	40
0.8-0.85	6
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9487	High Similarity	NPD3092	Approved
0.9174	High Similarity	NPD3094	Phase 2
0.9145	High Similarity	NPD3091	Approved
0.8678	High Similarity	NPD3095	Discontinued
0.8525	High Similarity	NPD4059	Approved
0.8321	Intermediate Similarity	NPD5735	Approved
0.8281	Intermediate Similarity	NPD5736	Approved
0.8244	Intermediate Similarity	NPD3620	Phase 2
0.8244	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.808	Intermediate Similarity	NPD3019	Approved
0.803	Intermediate Similarity	NPD6663	Approved
0.7937	Intermediate Similarity	NPD2932	Approved
0.7923	Intermediate Similarity	NPD4624	Approved
0.7868	Intermediate Similarity	NPD7743	Approved
0.7868	Intermediate Similarity	NPD7742	Approved
0.7836	Intermediate Similarity	NPD4140	Approved
0.7829	Intermediate Similarity	NPD5327	Phase 3
0.7769	Intermediate Similarity	NPD3021	Approved
0.7769	Intermediate Similarity	NPD3022	Approved
0.7759	Intermediate Similarity	NPD3020	Approved
0.775	Intermediate Similarity	NPD2342	Discontinued
0.7727	Intermediate Similarity	NPD2861	Phase 2
0.7721	Intermediate Similarity	NPD6353	Approved
0.7626	Intermediate Similarity	NPD5763	Approved
0.7626	Intermediate Similarity	NPD5762	Approved
0.7581	Intermediate Similarity	NPD7635	Approved
0.7535	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD3638	Discontinued
0.75	Intermediate Similarity	NPD2859	Approved
0.75	Intermediate Similarity	NPD2860	Approved
0.748	Intermediate Similarity	NPD4750	Phase 3
0.7462	Intermediate Similarity	NPD3023	Approved
0.7462	Intermediate Similarity	NPD3026	Approved
0.7444	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3024	Approved
0.7442	Intermediate Similarity	NPD4093	Discontinued
0.7442	Intermediate Similarity	NPD3025	Approved
0.7436	Intermediate Similarity	NPD288	Approved
0.7414	Intermediate Similarity	NPD2933	Approved
0.7414	Intermediate Similarity	NPD2934	Approved
0.7385	Intermediate Similarity	NPD2286	Discontinued
0.7379	Intermediate Similarity	NPD3645	Discontinued
0.735	Intermediate Similarity	NPD844	Approved
0.7293	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1201	Approved
0.7266	Intermediate Similarity	NPD3657	Discovery
0.7265	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1242	Phase 1
0.7231	Intermediate Similarity	NPD7741	Discontinued
0.7194	Intermediate Similarity	NPD4060	Phase 1
0.719	Intermediate Similarity	NPD846	Approved
0.719	Intermediate Similarity	NPD940	Approved
0.7179	Intermediate Similarity	NPD845	Approved
0.7153	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4721	Approved
0.7133	Intermediate Similarity	NPD4726	Approved
0.7133	Intermediate Similarity	NPD4725	Approved
0.7131	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1751	Approved
0.7109	Intermediate Similarity	NPD2228	Approved
0.7109	Intermediate Similarity	NPD2234	Approved
0.7109	Intermediate Similarity	NPD2229	Approved
0.7107	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3027	Phase 3
0.7101	Intermediate Similarity	NPD4625	Phase 3
0.7095	Intermediate Similarity	NPD6273	Approved
0.7092	Intermediate Similarity	NPD4097	Suspended
0.7071	Intermediate Similarity	NPD2238	Phase 2
0.7063	Intermediate Similarity	NPD1792	Phase 2
0.7059	Intermediate Similarity	NPD1809	Phase 2
0.7059	Intermediate Similarity	NPD4103	Phase 2
0.7059	Intermediate Similarity	NPD1470	Approved
0.7059	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5699	Approved
0.7037	Intermediate Similarity	NPD4659	Approved
0.7029	Intermediate Similarity	NPD2606	Approved
0.7029	Intermediate Similarity	NPD4908	Phase 1
0.7029	Intermediate Similarity	NPD3594	Approved
0.7029	Intermediate Similarity	NPD2605	Approved
0.7029	Intermediate Similarity	NPD3595	Approved
0.7015	Intermediate Similarity	NPD1610	Phase 2
0.7007	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9381	Approved
0.6992	Remote Similarity	NPD4626	Approved
0.6992	Remote Similarity	NPD9384	Approved
0.6978	Remote Similarity	NPD5155	Approved
0.6978	Remote Similarity	NPD5156	Approved
0.6966	Remote Similarity	NPD7037	Approved
0.6957	Remote Similarity	NPD3636	Approved
0.6957	Remote Similarity	NPD3637	Approved
0.6957	Remote Similarity	NPD3635	Approved
0.695	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1613	Approved
0.6929	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4749	Approved
0.6884	Remote Similarity	NPD2195	Approved
0.6884	Remote Similarity	NPD2194	Approved
0.6875	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD8166	Discontinued
0.6866	Remote Similarity	NPD5126	Approved
0.6866	Remote Similarity	NPD5125	Phase 3
0.6861	Remote Similarity	NPD6696	Suspended
0.685	Remote Similarity	NPD2684	Approved
0.6846	Remote Similarity	NPD5283	Phase 1
0.6846	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD2232	Approved
0.6838	Remote Similarity	NPD2233	Approved
0.6838	Remote Similarity	NPD2230	Approved
0.6831	Remote Similarity	NPD3059	Approved
0.6831	Remote Similarity	NPD3062	Approved
0.6831	Remote Similarity	NPD3061	Approved
0.6828	Remote Similarity	NPD5405	Approved
0.6828	Remote Similarity	NPD5406	Approved
0.6828	Remote Similarity	NPD5408	Approved
0.6828	Remote Similarity	NPD5404	Approved
0.6825	Remote Similarity	NPD1444	Approved
0.6825	Remote Similarity	NPD1445	Approved
0.6824	Remote Similarity	NPD8131	Suspended
0.6822	Remote Similarity	NPD228	Approved
0.6822	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD37	Approved
0.6809	Remote Similarity	NPD3764	Approved
0.6809	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6674	Discontinued
0.6791	Remote Similarity	NPD5691	Approved
0.6788	Remote Similarity	NPD9622	Approved
0.6783	Remote Similarity	NPD111	Approved
0.6763	Remote Similarity	NPD6584	Phase 3
0.6761	Remote Similarity	NPD8032	Phase 2
0.6761	Remote Similarity	NPD6405	Approved
0.6761	Remote Similarity	NPD6407	Approved
0.6742	Remote Similarity	NPD6671	Approved
0.6742	Remote Similarity	NPD7157	Approved
0.6741	Remote Similarity	NPD5846	Approved
0.6741	Remote Similarity	NPD6516	Phase 2
0.6739	Remote Similarity	NPD8651	Approved
0.6739	Remote Similarity	NPD1283	Approved
0.6736	Remote Similarity	NPD2157	Approved
0.6736	Remote Similarity	NPD6653	Approved
0.6736	Remote Similarity	NPD5314	Approved
0.6733	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7041	Phase 2
0.6716	Remote Similarity	NPD1548	Phase 1
0.6716	Remote Similarity	NPD5303	Approved
0.6716	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5304	Approved
0.6715	Remote Similarity	NPD2561	Approved
0.6715	Remote Similarity	NPD2562	Approved
0.6709	Remote Similarity	NPD6234	Discontinued
0.6689	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4965	Approved
0.6688	Remote Similarity	NPD4966	Approved
0.6688	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7266	Discontinued
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD3300	Phase 2
0.6667	Remote Similarity	NPD497	Approved
0.6667	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3892	Phase 2
0.6644	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5588	Approved
0.6643	Remote Similarity	NPD9619	Approved
0.6643	Remote Similarity	NPD9621	Approved
0.6643	Remote Similarity	NPD9620	Approved
0.6642	Remote Similarity	NPD16	Approved
0.6642	Remote Similarity	NPD856	Approved
0.6641	Remote Similarity	NPD7843	Approved
0.6641	Remote Similarity	NPD9379	Approved
0.6641	Remote Similarity	NPD9377	Approved
0.6625	Remote Similarity	NPD8127	Discontinued
0.6623	Remote Similarity	NPD2420	Approved
0.6623	Remote Similarity	NPD2421	Approved
0.6621	Remote Similarity	NPD823	Approved
0.6621	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD817	Approved
0.662	Remote Similarity	NPD7095	Approved
0.6618	Remote Similarity	NPD2667	Approved
0.6618	Remote Similarity	NPD4589	Approved
0.6618	Remote Similarity	NPD2668	Approved
0.6615	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD2489	Approved
0.6605	Remote Similarity	NPD27	Approved
0.66	Remote Similarity	NPD6190	Approved
0.6596	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD2231	Phase 2
0.6594	Remote Similarity	NPD2235	Phase 2
0.6591	Remote Similarity	NPD495	Approved
0.6591	Remote Similarity	NPD496	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