NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.04
Volume:	209.832
LogP:	1.934
LogD:	1.418
LogS:	-4.478
# Rotatable Bonds:	0
TPSA:	91.67
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.381
Synthetic Accessibility Score:	3.168
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.74
MDCK Permeability:	1.6398231309722178e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.528

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	96.66120147705078%
Volume Distribution (VD):	0.445
Pgp-substrate:	1.475702166557312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.9
CYP1A2-substrate:	0.476
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.344
CYP2C9-substrate:	0.654
CYP2D6-inhibitor:	0.355
CYP2D6-substrate:	0.258
CYP3A4-inhibitor:	0.68
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	3.379
Half-life (T1/2):	0.356

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.868
Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.764
Carcinogencity:	0.329
Eye Corrosion:	0.043
Eye Irritation:	0.909
Respiratory Toxicity:	0.112

Download Data

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

Natural Product: NPC1991

Natural Product ID:	NPC1991
*Common Name:**	YWAFPBDUACLSIJ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	8-Hydroxydroserone
Standard InCHIKey:	YWAFPBDUACLSIJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H8O5/c1-4-9(14)7-5(12)2-3-6(13)8(7)11(16)10(4)15/h2-3,12-13,15H,1H3
SMILES:	CC1=C(O)C(=O)c2c(C1=O)c(O)ccc2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1915218
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1007/s004360050318]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s004360050318]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22019229]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[9371362]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[9371362]
NPO3062	Drosera whittakeri	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3062	Drosera whittakeri	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11416	Helleborus torquatus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1494	Nepenthes gracilis	Species	Nepenthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8761	Gelidium amansii	Species	Gelidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1851	Monanthotaxis cauliflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11416	Helleborus torquatus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3062	Drosera whittakeri	Species	Droseraceae	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
EC50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	100000.0	nM	PMID[508340]

☑ 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 NPC1991 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	327
0.1-0.2	1620
0.2-0.3	4355
0.3-0.4	11781
0.4-0.5	7401
0.5-0.6	6476
0.6-0.7	8027
0.7-0.8	2412
0.8-0.85	218
0.85-0.9	63
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9593	High Similarity	NPC278928
0.9508	High Similarity	NPC231774
0.9504	High Similarity	NPC310540
0.92	High Similarity	NPC237225
0.9194	High Similarity	NPC306765
0.9167	High Similarity	NPC232178
0.9091	High Similarity	NPC285829
0.9091	High Similarity	NPC206778
0.9062	High Similarity	NPC246693
0.9062	High Similarity	NPC110609
0.9062	High Similarity	NPC242358
0.9048	High Similarity	NPC165257
0.904	High Similarity	NPC3224
0.904	High Similarity	NPC51037
0.8984	High Similarity	NPC205992
0.8968	High Similarity	NPC471530
0.8915	High Similarity	NPC309430
0.8915	High Similarity	NPC88864
0.8906	High Similarity	NPC198305
0.8889	High Similarity	NPC96915
0.8871	High Similarity	NPC307174
0.8846	High Similarity	NPC193169
0.8846	High Similarity	NPC171968
0.881	High Similarity	NPC103540
0.876	High Similarity	NPC108288
0.875	High Similarity	NPC282923
0.8722	High Similarity	NPC305060
0.871	High Similarity	NPC472046
0.8702	High Similarity	NPC254603
0.8692	High Similarity	NPC205360
0.8686	High Similarity	NPC477409
0.8682	High Similarity	NPC99731
0.8678	High Similarity	NPC240163
0.8651	High Similarity	NPC375356
0.8647	High Similarity	NPC86524
0.8647	High Similarity	NPC474813
0.8647	High Similarity	NPC272268
0.8626	High Similarity	NPC70622
0.8615	High Similarity	NPC117609
0.8615	High Similarity	NPC475741
0.8605	High Similarity	NPC179898
0.8593	High Similarity	NPC306835
0.8593	High Similarity	NPC471602
0.8593	High Similarity	NPC476477
0.8593	High Similarity	NPC216312
0.8593	High Similarity	NPC114620
0.8593	High Similarity	NPC29771
0.8593	High Similarity	NPC103337
0.8593	High Similarity	NPC111422
0.8593	High Similarity	NPC299405
0.8593	High Similarity	NPC256463
0.8583	High Similarity	NPC173978
0.8583	High Similarity	NPC234890
0.8583	High Similarity	NPC74507
0.8582	High Similarity	NPC245923
0.8582	High Similarity	NPC471452
0.8582	High Similarity	NPC147418
0.8571	High Similarity	NPC300274
0.8571	High Similarity	NPC129752
0.8571	High Similarity	NPC22222
0.8571	High Similarity	NPC281513
0.855	High Similarity	NPC17083
0.8538	High Similarity	NPC34414
0.8538	High Similarity	NPC146647
0.8537	High Similarity	NPC269414
0.8529	High Similarity	NPC37992
0.8529	High Similarity	NPC327916
0.8529	High Similarity	NPC42262
0.8529	High Similarity	NPC220496
0.8529	High Similarity	NPC241349
0.8529	High Similarity	NPC32749
0.8529	High Similarity	NPC147542
0.8527	High Similarity	NPC324209
0.8519	High Similarity	NPC173980
0.8507	High Similarity	NPC155211
0.8496	Intermediate Similarity	NPC288089
0.8485	Intermediate Similarity	NPC58685
0.8485	Intermediate Similarity	NPC17843
0.848	Intermediate Similarity	NPC473662
0.848	Intermediate Similarity	NPC7151
0.848	Intermediate Similarity	NPC216297
0.8473	Intermediate Similarity	NPC136588
0.8473	Intermediate Similarity	NPC55949
0.8473	Intermediate Similarity	NPC199253
0.8467	Intermediate Similarity	NPC471444
0.8467	Intermediate Similarity	NPC257003
0.8462	Intermediate Similarity	NPC767
0.8462	Intermediate Similarity	NPC247250
0.8456	Intermediate Similarity	NPC143438
0.8455	Intermediate Similarity	NPC477453
0.845	Intermediate Similarity	NPC49647
0.845	Intermediate Similarity	NPC295202
0.845	Intermediate Similarity	NPC227741
0.845	Intermediate Similarity	NPC136342
0.8438	Intermediate Similarity	NPC68756
0.8438	Intermediate Similarity	NPC152525
0.8438	Intermediate Similarity	NPC142956
0.8433	Intermediate Similarity	NPC161632
0.8433	Intermediate Similarity	NPC283088
0.8433	Intermediate Similarity	NPC14377
0.8421	Intermediate Similarity	NPC115458
0.8409	Intermediate Similarity	NPC244699
0.8406	Intermediate Similarity	NPC474300
0.8385	Intermediate Similarity	NPC45537
0.8374	Intermediate Similarity	NPC161304
0.8372	Intermediate Similarity	NPC131799
0.837	Intermediate Similarity	NPC315275
0.837	Intermediate Similarity	NPC474311
0.8359	Intermediate Similarity	NPC477153
0.8359	Intermediate Similarity	NPC135062
0.8358	Intermediate Similarity	NPC50924
0.8358	Intermediate Similarity	NPC44437
0.8346	Intermediate Similarity	NPC477406
0.8346	Intermediate Similarity	NPC478190
0.8345	Intermediate Similarity	NPC476473
0.8333	Intermediate Similarity	NPC187843
0.8333	Intermediate Similarity	NPC31539
0.8333	Intermediate Similarity	NPC124365
0.8333	Intermediate Similarity	NPC283292
0.8321	Intermediate Similarity	NPC477408
0.8321	Intermediate Similarity	NPC48248
0.8309	Intermediate Similarity	NPC53206
0.8309	Intermediate Similarity	NPC53414
0.8308	Intermediate Similarity	NPC15837
0.8308	Intermediate Similarity	NPC160499
0.8286	Intermediate Similarity	NPC274085
0.8286	Intermediate Similarity	NPC89664
0.8284	Intermediate Similarity	NPC53896
0.8284	Intermediate Similarity	NPC52407
0.8284	Intermediate Similarity	NPC225051
0.8284	Intermediate Similarity	NPC314048
0.8273	Intermediate Similarity	NPC291078
0.8271	Intermediate Similarity	NPC85342
0.8248	Intermediate Similarity	NPC61398
0.8248	Intermediate Similarity	NPC416
0.8248	Intermediate Similarity	NPC13715
0.8248	Intermediate Similarity	NPC61590
0.824	Intermediate Similarity	NPC125252
0.8239	Intermediate Similarity	NPC476821
0.8235	Intermediate Similarity	NPC472308
0.8235	Intermediate Similarity	NPC254847
0.8235	Intermediate Similarity	NPC141934
0.8231	Intermediate Similarity	NPC123506
0.8227	Intermediate Similarity	NPC471683
0.8222	Intermediate Similarity	NPC166480
0.8222	Intermediate Similarity	NPC282780
0.8222	Intermediate Similarity	NPC12070
0.8217	Intermediate Similarity	NPC273683
0.8214	Intermediate Similarity	NPC238629
0.8214	Intermediate Similarity	NPC469885
0.8214	Intermediate Similarity	NPC143898
0.8201	Intermediate Similarity	NPC110810
0.8195	Intermediate Similarity	NPC147757
0.8195	Intermediate Similarity	NPC31799
0.8188	Intermediate Similarity	NPC242994
0.8188	Intermediate Similarity	NPC26924
0.8188	Intermediate Similarity	NPC295339
0.8188	Intermediate Similarity	NPC138099
0.8175	Intermediate Similarity	NPC471905
0.8175	Intermediate Similarity	NPC41567
0.8169	Intermediate Similarity	NPC300540
0.8168	Intermediate Similarity	NPC472047
0.8162	Intermediate Similarity	NPC80035
0.8162	Intermediate Similarity	NPC249272
0.8156	Intermediate Similarity	NPC471906
0.8156	Intermediate Similarity	NPC29932
0.8148	Intermediate Similarity	NPC294226
0.8148	Intermediate Similarity	NPC267205
0.8148	Intermediate Similarity	NPC114183
0.814	Intermediate Similarity	NPC282577
0.814	Intermediate Similarity	NPC91478
0.8134	Intermediate Similarity	NPC72669
0.8134	Intermediate Similarity	NPC474517
0.8129	Intermediate Similarity	NPC156872
0.8129	Intermediate Similarity	NPC183345
0.8129	Intermediate Similarity	NPC169452
0.8129	Intermediate Similarity	NPC315578
0.8129	Intermediate Similarity	NPC181560
0.8125	Intermediate Similarity	NPC190971
0.812	Intermediate Similarity	NPC92624
0.8102	Intermediate Similarity	NPC38158
0.8102	Intermediate Similarity	NPC193358
0.8099	Intermediate Similarity	NPC474630
0.8099	Intermediate Similarity	NPC28632
0.8099	Intermediate Similarity	NPC224584
0.8092	Intermediate Similarity	NPC287473
0.8092	Intermediate Similarity	NPC477454
0.8092	Intermediate Similarity	NPC201728
0.8092	Intermediate Similarity	NPC262671
0.8088	Intermediate Similarity	NPC270899
0.8088	Intermediate Similarity	NPC287604
0.8088	Intermediate Similarity	NPC472262
0.8088	Intermediate Similarity	NPC161964
0.8085	Intermediate Similarity	NPC471682
0.8077	Intermediate Similarity	NPC182646
0.8074	Intermediate Similarity	NPC175738
0.8062	Intermediate Similarity	NPC198336
0.8062	Intermediate Similarity	NPC120545
0.806	Intermediate Similarity	NPC27659
0.806	Intermediate Similarity	NPC259942

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 NPC1991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	317
0.1-0.2	973
0.2-0.3	1592
0.3-0.4	2927
0.4-0.5	1956
0.5-0.6	999
0.6-0.7	342
0.7-0.8	40
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.881	High Similarity	NPD1470	Approved
0.876	High Similarity	NPD405	Clinical (unspecified phase)
0.864	High Similarity	NPD1201	Approved
0.8235	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD3300	Phase 2
0.7681	Intermediate Similarity	NPD943	Approved
0.7655	Intermediate Similarity	NPD7390	Discontinued
0.7635	Intermediate Similarity	NPD3226	Approved
0.7535	Intermediate Similarity	NPD5408	Approved
0.7535	Intermediate Similarity	NPD5404	Approved
0.7535	Intermediate Similarity	NPD5405	Approved
0.7535	Intermediate Similarity	NPD5406	Approved
0.7483	Intermediate Similarity	NPD2346	Discontinued
0.7431	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2935	Discontinued
0.7381	Intermediate Similarity	NPD74	Approved
0.7381	Intermediate Similarity	NPD9266	Approved
0.7368	Intermediate Similarity	NPD2932	Approved
0.7365	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD9493	Approved
0.7302	Intermediate Similarity	NPD9263	Approved
0.7302	Intermediate Similarity	NPD9267	Approved
0.7302	Intermediate Similarity	NPD9264	Approved
0.7299	Intermediate Similarity	NPD1164	Approved
0.7248	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1471	Phase 3
0.7239	Intermediate Similarity	NPD3019	Approved
0.7236	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1607	Approved
0.72	Intermediate Similarity	NPD1512	Approved
0.7183	Intermediate Similarity	NPD1240	Approved
0.7178	Intermediate Similarity	NPD5031	Approved
0.7178	Intermediate Similarity	NPD5029	Approved
0.7178	Intermediate Similarity	NPD5027	Approved
0.7165	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD7635	Approved
0.7143	Intermediate Similarity	NPD2800	Approved
0.7133	Intermediate Similarity	NPD2533	Approved
0.7133	Intermediate Similarity	NPD2534	Approved
0.7133	Intermediate Similarity	NPD2532	Approved
0.7123	Intermediate Similarity	NPD2344	Approved
0.7107	Intermediate Similarity	NPD6232	Discontinued
0.7103	Intermediate Similarity	NPD1510	Phase 2
0.7097	Intermediate Similarity	NPD2801	Approved
0.7095	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7473	Discontinued
0.7067	Intermediate Similarity	NPD1511	Approved
0.7045	Intermediate Similarity	NPD9281	Approved
0.7042	Intermediate Similarity	NPD2313	Discontinued
0.7042	Intermediate Similarity	NPD3764	Approved
0.703	Intermediate Similarity	NPD4955	Approved
0.703	Intermediate Similarity	NPD4954	Approved
0.703	Intermediate Similarity	NPD5026	Approved
0.703	Intermediate Similarity	NPD36	Approved
0.703	Intermediate Similarity	NPD5028	Approved
0.703	Intermediate Similarity	NPD5034	Approved
0.7014	Intermediate Similarity	NPD447	Suspended
0.7	Intermediate Similarity	NPD2798	Approved
0.6992	Remote Similarity	NPD288	Approved
0.6986	Remote Similarity	NPD2799	Discontinued
0.6984	Remote Similarity	NPD9261	Approved
0.697	Remote Similarity	NPD5030	Phase 2
0.6964	Remote Similarity	NPD5037	Approved
0.6964	Remote Similarity	NPD8150	Discontinued
0.6964	Remote Similarity	NPD5038	Approved
0.6963	Remote Similarity	NPD9545	Approved
0.6957	Remote Similarity	NPD9269	Phase 2
0.6957	Remote Similarity	NPD9717	Approved
0.6937	Remote Similarity	NPD6959	Discontinued
0.6933	Remote Similarity	NPD2309	Approved
0.6929	Remote Similarity	NPD1203	Approved
0.6923	Remote Similarity	NPD4750	Phase 3
0.6923	Remote Similarity	NPD411	Approved
0.6912	Remote Similarity	NPD9268	Approved
0.6911	Remote Similarity	NPD844	Approved
0.6905	Remote Similarity	NPD5036	Approved
0.6901	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3882	Suspended
0.6892	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6836	Approved
0.6879	Remote Similarity	NPD7819	Suspended
0.6879	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3750	Approved
0.6846	Remote Similarity	NPD1549	Phase 2
0.6835	Remote Similarity	NPD5402	Approved
0.6824	Remote Similarity	NPD1551	Phase 2
0.6818	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1934	Approved
0.6812	Remote Similarity	NPD3026	Approved
0.6812	Remote Similarity	NPD3023	Approved
0.6797	Remote Similarity	NPD1237	Approved
0.6791	Remote Similarity	NPD497	Approved
0.6788	Remote Similarity	NPD3025	Approved
0.6788	Remote Similarity	NPD3024	Approved
0.6786	Remote Similarity	NPD1755	Approved
0.6784	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD230	Phase 1
0.6769	Remote Similarity	NPD2342	Discontinued
0.6738	Remote Similarity	NPD1283	Approved
0.6735	Remote Similarity	NPD6651	Approved
0.6726	Remote Similarity	NPD5032	Approved
0.6724	Remote Similarity	NPD6534	Approved
0.6724	Remote Similarity	NPD6535	Approved
0.6718	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD496	Approved
0.6716	Remote Similarity	NPD498	Approved
0.6716	Remote Similarity	NPD495	Approved
0.6714	Remote Similarity	NPD1608	Approved
0.669	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4380	Phase 2
0.6688	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5033	Approved
0.6667	Remote Similarity	NPD164	Approved
0.6667	Remote Similarity	NPD5951	Approved
0.6667	Remote Similarity	NPD1651	Approved
0.6648	Remote Similarity	NPD7282	Approved
0.6646	Remote Similarity	NPD7075	Discontinued
0.6646	Remote Similarity	NPD3749	Approved
0.6645	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD520	Approved
0.6643	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6778	Approved
0.6629	Remote Similarity	NPD6776	Approved
0.6629	Remote Similarity	NPD6779	Approved
0.6629	Remote Similarity	NPD6781	Approved
0.6629	Remote Similarity	NPD6780	Approved
0.6629	Remote Similarity	NPD6782	Approved
0.6629	Remote Similarity	NPD6777	Approved
0.6627	Remote Similarity	NPD3751	Discontinued
0.6626	Remote Similarity	NPD1247	Approved
0.6625	Remote Similarity	NPD3817	Phase 2
0.6625	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6799	Approved
0.662	Remote Similarity	NPD6696	Suspended
0.662	Remote Similarity	NPD1876	Approved
0.6619	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD4626	Approved
0.6613	Remote Similarity	NPD845	Approved
0.661	Remote Similarity	NPD4975	Approved
0.661	Remote Similarity	NPD7700	Phase 2
0.661	Remote Similarity	NPD7699	Phase 2
0.661	Remote Similarity	NPD4974	Approved
0.6609	Remote Similarity	NPD5968	Phase 3
0.6606	Remote Similarity	NPD6166	Phase 2
0.6606	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6844	Discontinued
0.66	Remote Similarity	NPD6100	Approved
0.66	Remote Similarity	NPD6099	Approved
0.6597	Remote Similarity	NPD9494	Approved
0.6596	Remote Similarity	NPD4878	Approved
0.6588	Remote Similarity	NPD5035	Approved
0.6585	Remote Similarity	NPD5711	Approved
0.6585	Remote Similarity	NPD5710	Approved
0.6582	Remote Similarity	NPD6599	Discontinued
0.6579	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD5544	Approved
0.6564	Remote Similarity	NPD5494	Approved
0.6562	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD7003	Approved
0.6536	Remote Similarity	NPD8166	Discontinued
0.6533	Remote Similarity	NPD3748	Approved
0.6531	Remote Similarity	NPD6663	Approved
0.6529	Remote Similarity	NPD650	Approved
0.6529	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1281	Approved
0.6525	Remote Similarity	NPD1611	Approved
0.6519	Remote Similarity	NPD7697	Approved
0.6519	Remote Similarity	NPD7696	Phase 3
0.6519	Remote Similarity	NPD7698	Approved
0.6519	Remote Similarity	NPD7435	Discontinued
0.6512	Remote Similarity	NPD846	Approved
0.6512	Remote Similarity	NPD940	Approved
0.65	Remote Similarity	NPD17	Approved
0.65	Remote Similarity	NPD6801	Discontinued
0.65	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD920	Approved
0.6496	Remote Similarity	NPD6671	Approved
0.6494	Remote Similarity	NPD6190	Approved
0.6493	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD8312	Approved
0.6491	Remote Similarity	NPD8313	Approved
0.649	Remote Similarity	NPD2796	Approved
0.6488	Remote Similarity	NPD5844	Phase 1
0.6484	Remote Similarity	NPD7870	Phase 2
0.6484	Remote Similarity	NPD3020	Approved
0.6484	Remote Similarity	NPD7871	Phase 2
0.6483	Remote Similarity	NPD5736	Approved
0.6479	Remote Similarity	NPD1481	Phase 2
0.6479	Remote Similarity	NPD3972	Approved
0.6477	Remote Similarity	NPD6212	Phase 3
0.6477	Remote Similarity	NPD6213	Phase 3
0.6477	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD8434	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