NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.09
Volume:	267.589
LogP:	4.009
LogD:	2.429
LogS:	-3.294
# Rotatable Bonds:	2
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.378
Synthetic Accessibility Score:	3.015
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.068
MDCK Permeability:	1.4763633771508466e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.586
30% Bioavailability (F30%):	0.338

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	99.6581039428711%
Volume Distribution (VD):	0.442
Pgp-substrate:	3.3813278675079346%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.612
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.443
CYP2C9-substrate:	0.602
CYP2D6-inhibitor:	0.586
CYP2D6-substrate:	0.546
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.129

ADMET: Excretion

Clearance (CL):	7.447
Half-life (T1/2):	0.887

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.153
Drug-inuced Liver Injury (DILI):	0.625
AMES Toxicity:	0.782
Rat Oral Acute Toxicity:	0.532
Maximum Recommended Daily Dose:	0.779
Skin Sensitization:	0.961
Carcinogencity:	0.741
Eye Corrosion:	0.006
Eye Irritation:	0.931
Respiratory Toxicity:	0.72

Download Data

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

Natural Product: NPC231774

Natural Product ID:	NPC231774
*Common Name:**	XOFJIZXNAOYRAW-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	5-Hydroxylapachol
Standard InCHIKey:	XOFJIZXNAOYRAW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O4/c1-8(2)6-7-10-13(17)12-9(14(18)15(10)19)4-3-5-11(12)16/h3-6,16,19H,7H2,1-2H3/p-1
SMILES:	CC(=CCC1=C(C(=O)c2cccc(c2C1=O)[O-])O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1089642
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0001547] Vitamin K compounds

*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
NPO18640	Tectona grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18640	Tectona grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18640	Tectona grandis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18640	Tectona grandis	Species	Lamiaceae	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
GI50	10

Activity Type	# Activity
Cell Line	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	GI50	=	570.0	nM	PMID[505313]
NPT1723	Cell Line	HBL-100	Homo sapiens	GI50	=	600.0	nM	PMID[505313]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	420.0	nM	PMID[505313]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	700.0	nM	PMID[505313]
NPT396	Cell Line	T47D	Homo sapiens	GI50	=	8100.0	nM	PMID[505313]
NPT1183	Cell Line	WiDr	Homo sapiens	GI50	=	6300.0	nM	PMID[505313]
NPT1723	Cell Line	HBL-100	Homo sapiens	GI50	=	600.0	nM	PMID[505314]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	420.0	nM	PMID[505314]
NPT1577	Cell Line	SW1573	Homo sapiens	GI50	=	700.0	nM	PMID[505314]
NPT1183	Cell Line	WiDr	Homo sapiens	GI50	=	6300.0	nM	PMID[505314]

☑ 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 NPC231774 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	300
0.1-0.2	1502
0.2-0.3	3610
0.3-0.4	9861
0.4-0.5	9390
0.5-0.6	5811
0.6-0.7	8132
0.7-0.8	3554
0.8-0.85	364
0.85-0.9	148
0.9-0.95	23
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC310540
0.9508	High Similarity	NPC1991
0.9508	High Similarity	NPC3224
0.9435	High Similarity	NPC278928
0.9412	High Similarity	NPC206778
0.9412	High Similarity	NPC285829
0.9365	High Similarity	NPC309430
0.9355	High Similarity	NPC165257
0.9355	High Similarity	NPC237225
0.9339	High Similarity	NPC307174
0.9268	High Similarity	NPC103540
0.9206	High Similarity	NPC198305
0.92	High Similarity	NPC282923
0.9194	High Similarity	NPC306765
0.9194	High Similarity	NPC51037
0.9141	High Similarity	NPC254603
0.9141	High Similarity	NPC171968
0.9127	High Similarity	NPC99731
0.9106	High Similarity	NPC375356
0.9076	High Similarity	NPC108288
0.9062	High Similarity	NPC246693
0.9062	High Similarity	NPC110609
0.9062	High Similarity	NPC242358
0.9024	High Similarity	NPC300274
0.8984	High Similarity	NPC205992
0.8976	High Similarity	NPC146647
0.8976	High Similarity	NPC34414
0.8931	High Similarity	NPC86524
0.8915	High Similarity	NPC70622
0.8915	High Similarity	NPC58685
0.8906	High Similarity	NPC475741
0.8906	High Similarity	NPC117609
0.8898	High Similarity	NPC179898
0.8889	High Similarity	NPC96915
0.888	High Similarity	NPC173978
0.888	High Similarity	NPC142956
0.8872	High Similarity	NPC103337
0.8872	High Similarity	NPC114620
0.8864	High Similarity	NPC471452
0.8855	High Similarity	NPC283088
0.8852	High Similarity	NPC232178
0.8846	High Similarity	NPC115458
0.8837	High Similarity	NPC244699
0.8837	High Similarity	NPC17083
0.8837	High Similarity	NPC205360
0.8833	High Similarity	NPC161304
0.88	High Similarity	NPC135062
0.8797	High Similarity	NPC173980
0.8788	High Similarity	NPC315275
0.8779	High Similarity	NPC44437
0.8779	High Similarity	NPC50924
0.8779	High Similarity	NPC288089
0.8769	High Similarity	NPC88864
0.876	High Similarity	NPC136588
0.876	High Similarity	NPC477453
0.876	High Similarity	NPC199253
0.876	High Similarity	NPC55949
0.875	High Similarity	NPC48248
0.874	High Similarity	NPC15837
0.873	High Similarity	NPC234890
0.873	High Similarity	NPC74507
0.8722	High Similarity	NPC53206
0.8722	High Similarity	NPC53414
0.8712	High Similarity	NPC161632
0.8702	High Similarity	NPC225051
0.8702	High Similarity	NPC193169
0.8702	High Similarity	NPC53896
0.8672	High Similarity	NPC324209
0.8672	High Similarity	NPC471530
0.8661	High Similarity	NPC123506
0.8657	High Similarity	NPC13715
0.8657	High Similarity	NPC416
0.8657	High Similarity	NPC61590
0.8657	High Similarity	NPC61398
0.8647	High Similarity	NPC141934
0.8647	High Similarity	NPC254847
0.8647	High Similarity	NPC272268
0.8647	High Similarity	NPC474813
0.8636	High Similarity	NPC166480
0.8636	High Similarity	NPC282780
0.8615	High Similarity	NPC31799
0.8594	High Similarity	NPC160499
0.8593	High Similarity	NPC306835
0.8593	High Similarity	NPC29771
0.8593	High Similarity	NPC476477
0.8593	High Similarity	NPC256463
0.8593	High Similarity	NPC242994
0.8593	High Similarity	NPC26924
0.8593	High Similarity	NPC216312
0.8593	High Similarity	NPC295339
0.8593	High Similarity	NPC111422
0.8593	High Similarity	NPC477408
0.8593	High Similarity	NPC299405
0.8593	High Similarity	NPC471602
0.8593	High Similarity	NPC138099
0.8583	High Similarity	NPC68756
0.8583	High Similarity	NPC152525
0.8582	High Similarity	NPC245923
0.8582	High Similarity	NPC305060
0.8582	High Similarity	NPC471905
0.8571	High Similarity	NPC91478
0.8571	High Similarity	NPC22222
0.8571	High Similarity	NPC281513
0.8571	High Similarity	NPC282577
0.8571	High Similarity	NPC80035
0.8561	High Similarity	NPC294226
0.8561	High Similarity	NPC52407
0.8551	High Similarity	NPC477409
0.854	High Similarity	NPC291078
0.8529	High Similarity	NPC181560
0.8529	High Similarity	NPC37992
0.8529	High Similarity	NPC42262
0.8529	High Similarity	NPC169452
0.8529	High Similarity	NPC220496
0.8529	High Similarity	NPC241349
0.8529	High Similarity	NPC32749
0.8529	High Similarity	NPC147542
0.8529	High Similarity	NPC327916
0.8529	High Similarity	NPC315578
0.8525	High Similarity	NPC240163
0.8507	High Similarity	NPC474311
0.8507	High Similarity	NPC38158
0.8507	High Similarity	NPC193358
0.8507	High Similarity	NPC155211
0.8496	Intermediate Similarity	NPC12070
0.8492	Intermediate Similarity	NPC120545
0.8485	Intermediate Similarity	NPC17843
0.8485	Intermediate Similarity	NPC477406
0.848	Intermediate Similarity	NPC473662
0.848	Intermediate Similarity	NPC216297
0.848	Intermediate Similarity	NPC7151
0.8473	Intermediate Similarity	NPC27659
0.8468	Intermediate Similarity	NPC41567
0.8467	Intermediate Similarity	NPC257003
0.8467	Intermediate Similarity	NPC471444
0.8462	Intermediate Similarity	NPC767
0.8462	Intermediate Similarity	NPC247250
0.8456	Intermediate Similarity	NPC1268
0.8456	Intermediate Similarity	NPC143438
0.845	Intermediate Similarity	NPC8745
0.8444	Intermediate Similarity	NPC238108
0.8444	Intermediate Similarity	NPC147418
0.8433	Intermediate Similarity	NPC249272
0.8433	Intermediate Similarity	NPC258502
0.8425	Intermediate Similarity	NPC164947
0.8421	Intermediate Similarity	NPC114183
0.8421	Intermediate Similarity	NPC314048
0.8421	Intermediate Similarity	NPC267205
0.8417	Intermediate Similarity	NPC29932
0.8417	Intermediate Similarity	NPC471906
0.8413	Intermediate Similarity	NPC190971
0.8413	Intermediate Similarity	NPC472046
0.8409	Intermediate Similarity	NPC72669
0.8409	Intermediate Similarity	NPC474517
0.8406	Intermediate Similarity	NPC19631
0.8406	Intermediate Similarity	NPC239136
0.8406	Intermediate Similarity	NPC474300
0.8406	Intermediate Similarity	NPC193555
0.8403	Intermediate Similarity	NPC224584
0.8397	Intermediate Similarity	NPC109123
0.8397	Intermediate Similarity	NPC25736
0.8397	Intermediate Similarity	NPC171460
0.8397	Intermediate Similarity	NPC92624
0.8394	Intermediate Similarity	NPC96421
0.8394	Intermediate Similarity	NPC203063
0.8394	Intermediate Similarity	NPC183345
0.8394	Intermediate Similarity	NPC156872
0.8387	Intermediate Similarity	NPC125252
0.8387	Intermediate Similarity	NPC269414
0.8382	Intermediate Similarity	NPC4214
0.8372	Intermediate Similarity	NPC10926
0.8372	Intermediate Similarity	NPC287473
0.8372	Intermediate Similarity	NPC477454
0.8369	Intermediate Similarity	NPC476821
0.8359	Intermediate Similarity	NPC477153
0.8359	Intermediate Similarity	NPC273683
0.8359	Intermediate Similarity	NPC182646
0.8358	Intermediate Similarity	NPC161964
0.8358	Intermediate Similarity	NPC287604
0.8358	Intermediate Similarity	NPC472262
0.8358	Intermediate Similarity	NPC270899
0.8357	Intermediate Similarity	NPC28632
0.8357	Intermediate Similarity	NPC474630
0.8346	Intermediate Similarity	NPC478190
0.8346	Intermediate Similarity	NPC175738
0.8345	Intermediate Similarity	NPC471682
0.8345	Intermediate Similarity	NPC476473
0.8345	Intermediate Similarity	NPC21873
0.8333	Intermediate Similarity	NPC204045
0.8333	Intermediate Similarity	NPC259942
0.8333	Intermediate Similarity	NPC110810
0.8333	Intermediate Similarity	NPC31539
0.8333	Intermediate Similarity	NPC246638
0.8333	Intermediate Similarity	NPC124365
0.8333	Intermediate Similarity	NPC283292
0.8333	Intermediate Similarity	NPC305845
0.8321	Intermediate Similarity	NPC96024
0.8321	Intermediate Similarity	NPC95537
0.8321	Intermediate Similarity	NPC24869
0.8321	Intermediate Similarity	NPC190457

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 NPC231774 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	943
0.2-0.3	1415
0.3-0.4	2652
0.4-0.5	2158
0.5-0.6	1164
0.6-0.7	422
0.7-0.8	83
0.8-0.85	4
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9268	High Similarity	NPD1470	Approved
0.9076	High Similarity	NPD405	Clinical (unspecified phase)
0.8943	High Similarity	NPD1201	Approved
0.8647	High Similarity	NPD1509	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD3300	Phase 2
0.8074	Intermediate Similarity	NPD943	Approved
0.7914	Intermediate Similarity	NPD5408	Approved
0.7914	Intermediate Similarity	NPD5404	Approved
0.7914	Intermediate Similarity	NPD5405	Approved
0.7914	Intermediate Similarity	NPD5406	Approved
0.7877	Intermediate Similarity	NPD3226	Approved
0.7778	Intermediate Similarity	NPD7390	Discontinued
0.773	Intermediate Similarity	NPD2346	Discontinued
0.7687	Intermediate Similarity	NPD1164	Approved
0.7661	Intermediate Similarity	NPD9266	Approved
0.7661	Intermediate Similarity	NPD74	Approved
0.7634	Intermediate Similarity	NPD2932	Approved
0.7606	Intermediate Similarity	NPD1471	Phase 3
0.7597	Intermediate Similarity	NPD9493	Approved
0.7589	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD9263	Approved
0.7581	Intermediate Similarity	NPD9267	Approved
0.7581	Intermediate Similarity	NPD9264	Approved
0.7571	Intermediate Similarity	NPD1607	Approved
0.7557	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD1240	Approved
0.7552	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3019	Approved
0.7483	Intermediate Similarity	NPD2344	Approved
0.7483	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1510	Phase 2
0.744	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2935	Discontinued
0.741	Intermediate Similarity	NPD3764	Approved
0.7372	Intermediate Similarity	NPD2798	Approved
0.7365	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2799	Discontinued
0.7329	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD9281	Approved
0.7286	Intermediate Similarity	NPD2313	Discontinued
0.7279	Intermediate Similarity	NPD2309	Approved
0.7273	Intermediate Similarity	NPD288	Approved
0.7258	Intermediate Similarity	NPD9261	Approved
0.7248	Intermediate Similarity	NPD2532	Approved
0.7248	Intermediate Similarity	NPD2533	Approved
0.7248	Intermediate Similarity	NPD2534	Approved
0.7218	Intermediate Similarity	NPD9545	Approved
0.7215	Intermediate Similarity	NPD6232	Discontinued
0.7211	Intermediate Similarity	NPD3750	Approved
0.7209	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7819	Suspended
0.7206	Intermediate Similarity	NPD9717	Approved
0.72	Intermediate Similarity	NPD1512	Approved
0.72	Intermediate Similarity	NPD1237	Approved
0.7192	Intermediate Similarity	NPD1549	Phase 2
0.719	Intermediate Similarity	NPD844	Approved
0.7188	Intermediate Similarity	NPD7473	Discontinued
0.7188	Intermediate Similarity	NPD4750	Phase 3
0.7178	Intermediate Similarity	NPD5031	Approved
0.7178	Intermediate Similarity	NPD5027	Approved
0.7178	Intermediate Similarity	NPD5029	Approved
0.7174	Intermediate Similarity	NPD1203	Approved
0.7163	Intermediate Similarity	NPD411	Approved
0.7143	Intermediate Similarity	NPD2800	Approved
0.7133	Intermediate Similarity	NPD447	Suspended
0.7123	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3882	Suspended
0.7109	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD9269	Phase 2
0.7067	Intermediate Similarity	NPD1511	Approved
0.7066	Intermediate Similarity	NPD8150	Discontinued
0.7059	Intermediate Similarity	NPD3026	Approved
0.7059	Intermediate Similarity	NPD3023	Approved
0.7055	Intermediate Similarity	NPD1551	Phase 2
0.7045	Intermediate Similarity	NPD5951	Approved
0.7037	Intermediate Similarity	NPD9268	Approved
0.7037	Intermediate Similarity	NPD3024	Approved
0.7037	Intermediate Similarity	NPD3025	Approved
0.7031	Intermediate Similarity	NPD2342	Discontinued
0.703	Intermediate Similarity	NPD5028	Approved
0.703	Intermediate Similarity	NPD4955	Approved
0.703	Intermediate Similarity	NPD4954	Approved
0.703	Intermediate Similarity	NPD5026	Approved
0.703	Intermediate Similarity	NPD5034	Approved
0.703	Intermediate Similarity	NPD36	Approved
0.7029	Intermediate Similarity	NPD1755	Approved
0.7023	Intermediate Similarity	NPD7635	Approved
0.702	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1876	Approved
0.6978	Remote Similarity	NPD1283	Approved
0.697	Remote Similarity	NPD5030	Phase 2
0.6964	Remote Similarity	NPD5037	Approved
0.6964	Remote Similarity	NPD5038	Approved
0.6962	Remote Similarity	NPD7075	Discontinued
0.6962	Remote Similarity	NPD3749	Approved
0.6957	Remote Similarity	NPD1608	Approved
0.6957	Remote Similarity	NPD4878	Approved
0.6937	Remote Similarity	NPD6959	Discontinued
0.6923	Remote Similarity	NPD1934	Approved
0.6913	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD1651	Approved
0.6905	Remote Similarity	NPD5036	Approved
0.6903	Remote Similarity	NPD4380	Phase 2
0.6903	Remote Similarity	NPD6599	Discontinued
0.6901	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD230	Phase 1
0.6885	Remote Similarity	NPD845	Approved
0.6882	Remote Similarity	NPD6836	Approved
0.6879	Remote Similarity	NPD2801	Approved
0.6879	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD520	Approved
0.6871	Remote Similarity	NPD3748	Approved
0.687	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8166	Discontinued
0.6867	Remote Similarity	NPD7003	Approved
0.6861	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4626	Approved
0.685	Remote Similarity	NPD1930	Approved
0.685	Remote Similarity	NPD1929	Approved
0.685	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6651	Approved
0.6842	Remote Similarity	NPD6799	Approved
0.6835	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3972	Approved
0.6831	Remote Similarity	NPD9494	Approved
0.6824	Remote Similarity	NPD6100	Approved
0.6824	Remote Similarity	NPD6099	Approved
0.6824	Remote Similarity	NPD2796	Approved
0.6812	Remote Similarity	NPD4879	Approved
0.6807	Remote Similarity	NPD650	Approved
0.6797	Remote Similarity	NPD164	Approved
0.6784	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD940	Approved
0.6772	Remote Similarity	NPD846	Approved
0.6772	Remote Similarity	NPD1932	Approved
0.6763	Remote Similarity	NPD1281	Approved
0.6759	Remote Similarity	NPD6663	Approved
0.6757	Remote Similarity	NPD4308	Phase 3
0.6755	Remote Similarity	NPD4628	Phase 3
0.6752	Remote Similarity	NPD7411	Suspended
0.6746	Remote Similarity	NPD3020	Approved
0.6739	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD17	Approved
0.6731	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5402	Approved
0.673	Remote Similarity	NPD2296	Approved
0.6726	Remote Similarity	NPD5032	Approved
0.6724	Remote Similarity	NPD6534	Approved
0.6724	Remote Similarity	NPD6535	Approved
0.6721	Remote Similarity	NPD7609	Phase 3
0.6716	Remote Similarity	NPD1241	Discontinued
0.6713	Remote Similarity	NPD5736	Approved
0.6709	Remote Similarity	NPD6801	Discontinued
0.6707	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6166	Phase 2
0.6694	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3268	Approved
0.6689	Remote Similarity	NPD1243	Approved
0.6687	Remote Similarity	NPD5711	Approved
0.6687	Remote Similarity	NPD5710	Approved
0.6687	Remote Similarity	NPD7768	Phase 2
0.6686	Remote Similarity	NPD8312	Approved
0.6686	Remote Similarity	NPD8313	Approved
0.6686	Remote Similarity	NPD5035	Approved
0.6667	Remote Similarity	NPD6832	Phase 2
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5033	Approved
0.6667	Remote Similarity	NPD3021	Approved
0.6667	Remote Similarity	NPD7631	Approved
0.6667	Remote Similarity	NPD497	Approved
0.6667	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3022	Approved
0.6648	Remote Similarity	NPD7282	Approved
0.6646	Remote Similarity	NPD3926	Phase 2
0.664	Remote Similarity	NPD1809	Phase 2
0.664	Remote Similarity	NPD2859	Approved
0.664	Remote Similarity	NPD2860	Approved
0.6639	Remote Similarity	NPD9256	Approved
0.6639	Remote Similarity	NPD9258	Approved
0.6629	Remote Similarity	NPD6781	Approved
0.6629	Remote Similarity	NPD6780	Approved
0.6629	Remote Similarity	NPD6779	Approved
0.6629	Remote Similarity	NPD6777	Approved
0.6629	Remote Similarity	NPD6782	Approved
0.6629	Remote Similarity	NPD6778	Approved
0.6629	Remote Similarity	NPD6776	Approved
0.6627	Remote Similarity	NPD3751	Discontinued
0.6626	Remote Similarity	NPD1247	Approved
0.6625	Remote Similarity	NPD3817	Phase 2
0.6624	Remote Similarity	NPD7458	Discontinued
0.6614	Remote Similarity	NPD2066	Phase 3
0.661	Remote Similarity	NPD7700	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