NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.1
Volume:	278.965
LogP:	2.111
LogD:	2.257
LogS:	-3.299
# Rotatable Bonds:	2
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.882
Synthetic Accessibility Score:	2.9
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.773
MDCK Permeability:	1.5681336662964895e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.563
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.476
Plasma Protein Binding (PPB):	96.31594848632812%
Volume Distribution (VD):	0.978
Pgp-substrate:	4.991147994995117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.717
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.792
CYP2C19-substrate:	0.738
CYP2C9-inhibitor:	0.588
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.802
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.239
CYP3A4-substrate:	0.661

ADMET: Excretion

Clearance (CL):	10.399
Half-life (T1/2):	0.485

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.494
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.084
Skin Sensitization:	0.661
Carcinogencity:	0.727
Eye Corrosion:	0.003
Eye Irritation:	0.41
Respiratory Toxicity:	0.108

Download Data

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

Natural Product: NPC478085

Natural Product ID:	NPC478085
*Common Name:**	(3S,4R)-4''-hydroxy-6,3''-dimethoxyisoflavan-4-ol
IUPAC Name:	(3S,4R)-3-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-chromen-4-ol
Synonyms:
Standard InCHIKey:	MOQNWTYYZUVPQT-WBMJQRKESA-N
Standard InCHI:	InChI=1S/C16H16O4/c1-19-15-8-10(6-7-13(15)17)12-9-20-14-5-3-2-4-11(14)16(12)18/h2-8,12,16-18H,9H2,1H3/t12-,16+/m1/s1
SMILES:	COC1=C(C=CC(=C1)[C@H]2COC3=CC=CC=C3[C@@H]2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	53326249
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002605] 3'-O-methylated isoflavonoids

*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
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	n.a.	n.a.	PMID[12444707]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	Yunnang Province, China	2000-OCT	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
IC50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	99500	nM	PMID[21138310]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	>	100000	nM	PMID[21138310]

☑ 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 NPC478085 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	413
0.1-0.2	1508
0.2-0.3	4141
0.3-0.4	11419
0.4-0.5	6945
0.5-0.6	3862
0.6-0.7	7205
0.7-0.8	5323
0.8-0.85	1043
0.85-0.9	613
0.9-0.95	215
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9549	High Similarity	NPC471389
0.9542	High Similarity	NPC306441
0.9542	High Similarity	NPC162659
0.9542	High Similarity	NPC270456
0.9542	High Similarity	NPC248727
0.9542	High Similarity	NPC16435
0.9542	High Similarity	NPC265433
0.9538	High Similarity	NPC317380
0.9474	High Similarity	NPC309124
0.9474	High Similarity	NPC184797
0.9466	High Similarity	NPC112246
0.9466	High Similarity	NPC61946
0.9466	High Similarity	NPC47398
0.9466	High Similarity	NPC260898
0.9466	High Similarity	NPC234333
0.9466	High Similarity	NPC470356
0.9466	High Similarity	NPC474206
0.9466	High Similarity	NPC121812
0.9466	High Similarity	NPC112939
0.9466	High Similarity	NPC94750
0.9462	High Similarity	NPC475840
0.9453	High Similarity	NPC5851
0.9453	High Similarity	NPC86030
0.9398	High Similarity	NPC25966
0.9398	High Similarity	NPC70682
0.9398	High Similarity	NPC236306
0.9398	High Similarity	NPC260741
0.9398	High Similarity	NPC473739
0.9398	High Similarity	NPC127218
0.9398	High Similarity	NPC245207
0.9398	High Similarity	NPC471388
0.9398	High Similarity	NPC232164
0.9398	High Similarity	NPC319647
0.9394	High Similarity	NPC10737
0.9394	High Similarity	NPC177160
0.9394	High Similarity	NPC156502
0.9394	High Similarity	NPC209985
0.9394	High Similarity	NPC269091
0.9394	High Similarity	NPC263367
0.9394	High Similarity	NPC474639
0.9394	High Similarity	NPC227503
0.9394	High Similarity	NPC302701
0.9394	High Similarity	NPC29799
0.9394	High Similarity	NPC477939
0.9394	High Similarity	NPC54743
0.9394	High Similarity	NPC230734
0.9375	High Similarity	NPC72529
0.9375	High Similarity	NPC245826
0.9375	High Similarity	NPC474178
0.9375	High Similarity	NPC252307
0.9333	High Similarity	NPC107161
0.9323	High Similarity	NPC326797
0.9323	High Similarity	NPC276490
0.9323	High Similarity	NPC107551
0.9323	High Similarity	NPC103976
0.9323	High Similarity	NPC474282
0.9323	High Similarity	NPC211549
0.9323	High Similarity	NPC102904
0.9323	High Similarity	NPC176051
0.9318	High Similarity	NPC164787
0.9318	High Similarity	NPC151224
0.9313	High Similarity	NPC11060
0.9313	High Similarity	NPC263064
0.9297	High Similarity	NPC292056
0.9297	High Similarity	NPC118533
0.9297	High Similarity	NPC41706
0.9297	High Similarity	NPC111247
0.9297	High Similarity	NPC118787
0.9297	High Similarity	NPC165045
0.9297	High Similarity	NPC163332
0.9297	High Similarity	NPC183181
0.9297	High Similarity	NPC319625
0.9297	High Similarity	NPC147821
0.9291	High Similarity	NPC148627
0.9291	High Similarity	NPC194519
0.9259	High Similarity	NPC263261
0.9259	High Similarity	NPC178054
0.9259	High Similarity	NPC35216
0.9259	High Similarity	NPC247291
0.9259	High Similarity	NPC87725
0.9248	High Similarity	NPC234952
0.9248	High Similarity	NPC470802
0.9248	High Similarity	NPC173660
0.9248	High Similarity	NPC472334
0.9248	High Similarity	NPC472336
0.9242	High Similarity	NPC193026
0.9242	High Similarity	NPC187616
0.9242	High Similarity	NPC170694
0.9242	High Similarity	NPC49603
0.9237	High Similarity	NPC253105
0.9237	High Similarity	NPC15658
0.9237	High Similarity	NPC185604
0.9237	High Similarity	NPC261619
0.9237	High Similarity	NPC61477
0.9237	High Similarity	NPC127624
0.9237	High Similarity	NPC202762
0.9237	High Similarity	NPC219876
0.9237	High Similarity	NPC78770
0.9237	High Similarity	NPC126029
0.9237	High Similarity	NPC201587
0.9237	High Similarity	NPC86655
0.9231	High Similarity	NPC174495
0.9231	High Similarity	NPC42300
0.9231	High Similarity	NPC153739
0.9231	High Similarity	NPC472338
0.9231	High Similarity	NPC64201
0.9231	High Similarity	NPC187998
0.9231	High Similarity	NPC241522
0.9231	High Similarity	NPC257582
0.9231	High Similarity	NPC145305
0.9231	High Similarity	NPC77040
0.9231	High Similarity	NPC92164
0.9231	High Similarity	NPC242807
0.9219	High Similarity	NPC178284
0.9219	High Similarity	NPC58607
0.9219	High Similarity	NPC191037
0.9213	High Similarity	NPC114901
0.9213	High Similarity	NPC293701
0.9213	High Similarity	NPC48990
0.9197	High Similarity	NPC473108
0.9197	High Similarity	NPC93323
0.9197	High Similarity	NPC45257
0.9197	High Similarity	NPC12641
0.9197	High Similarity	NPC280092
0.9191	High Similarity	NPC59841
0.9191	High Similarity	NPC204347
0.9191	High Similarity	NPC475891
0.9191	High Similarity	NPC2613
0.9185	High Similarity	NPC266197
0.9185	High Similarity	NPC259519
0.9185	High Similarity	NPC27495
0.9185	High Similarity	NPC291101
0.9185	High Similarity	NPC160283
0.9185	High Similarity	NPC254759
0.9173	High Similarity	NPC472337
0.9173	High Similarity	NPC195022
0.9173	High Similarity	NPC473413
0.9167	High Similarity	NPC168059
0.9167	High Similarity	NPC229442
0.9167	High Similarity	NPC26394
0.916	High Similarity	NPC220825
0.916	High Similarity	NPC277804
0.916	High Similarity	NPC474017
0.916	High Similarity	NPC268266
0.916	High Similarity	NPC42760
0.916	High Similarity	NPC472597
0.916	High Similarity	NPC268342
0.9154	High Similarity	NPC475875
0.9154	High Similarity	NPC212015
0.9147	High Similarity	NPC5428
0.9134	High Similarity	NPC471693
0.9124	High Similarity	NPC102044
0.9124	High Similarity	NPC47633
0.9124	High Similarity	NPC85264
0.9124	High Similarity	NPC477616
0.9118	High Similarity	NPC471414
0.9118	High Similarity	NPC311530
0.9111	High Similarity	NPC22517
0.9111	High Similarity	NPC32630
0.9111	High Similarity	NPC292882
0.9104	High Similarity	NPC77861
0.9098	High Similarity	NPC287745
0.9091	High Similarity	NPC160991
0.9091	High Similarity	NPC184447
0.9091	High Similarity	NPC470752
0.9091	High Similarity	NPC16208
0.9091	High Similarity	NPC35932
0.9091	High Similarity	NPC230219
0.9091	High Similarity	NPC7903
0.9084	High Similarity	NPC91291
0.9084	High Similarity	NPC143483
0.9077	High Similarity	NPC282703
0.9077	High Similarity	NPC21867
0.9077	High Similarity	NPC184733
0.9077	High Similarity	NPC98631
0.9077	High Similarity	NPC11258
0.9077	High Similarity	NPC470213
0.9077	High Similarity	NPC128208
0.9077	High Similarity	NPC186843
0.9077	High Similarity	NPC129570
0.9077	High Similarity	NPC206615
0.9077	High Similarity	NPC470084
0.9077	High Similarity	NPC45774
0.9065	High Similarity	NPC317053
0.9065	High Similarity	NPC190714
0.9065	High Similarity	NPC260397
0.9065	High Similarity	NPC99515
0.9065	High Similarity	NPC324492
0.9062	High Similarity	NPC109822
0.9062	High Similarity	NPC94276
0.9058	High Similarity	NPC63879
0.9058	High Similarity	NPC50250
0.9055	High Similarity	NPC71090
0.9051	High Similarity	NPC476356
0.9051	High Similarity	NPC253878
0.9044	High Similarity	NPC55793
0.9044	High Similarity	NPC22317
0.9037	High Similarity	NPC477938
0.903	High Similarity	NPC256262
0.9023	High Similarity	NPC158331

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 NPC478085 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	355
0.1-0.2	865
0.2-0.3	1801
0.3-0.4	2637
0.4-0.5	1655
0.5-0.6	925
0.6-0.7	694
0.7-0.8	204
0.8-0.85	9
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9237	High Similarity	NPD1613	Approved
0.9237	High Similarity	NPD1612	Clinical (unspecified phase)
0.9008	High Similarity	NPD3027	Phase 3
0.8931	High Similarity	NPD1529	Clinical (unspecified phase)
0.8855	High Similarity	NPD1530	Clinical (unspecified phase)
0.8647	High Similarity	NPD4908	Phase 1
0.8571	High Similarity	NPD2861	Phase 2
0.8538	High Similarity	NPD1610	Phase 2
0.8519	High Similarity	NPD4907	Clinical (unspecified phase)
0.8268	Intermediate Similarity	NPD5283	Phase 1
0.8255	Intermediate Similarity	NPD1934	Approved
0.8182	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6674	Discontinued
0.8134	Intermediate Similarity	NPD4749	Approved
0.8129	Intermediate Similarity	NPD3620	Phase 2
0.8129	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD4060	Phase 1
0.8116	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD228	Approved
0.8092	Intermediate Similarity	NPD1548	Phase 1
0.8079	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD4625	Phase 3
0.7987	Intermediate Similarity	NPD1653	Approved
0.7985	Intermediate Similarity	NPD1091	Approved
0.7962	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD6166	Phase 2
0.7962	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3021	Approved
0.7953	Intermediate Similarity	NPD3022	Approved
0.7941	Intermediate Similarity	NPD8651	Approved
0.7899	Intermediate Similarity	NPD3018	Phase 2
0.7874	Intermediate Similarity	NPD2684	Approved
0.7872	Intermediate Similarity	NPD1558	Phase 1
0.7868	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD7157	Approved
0.7857	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2801	Approved
0.7832	Intermediate Similarity	NPD4536	Approved
0.7832	Intermediate Similarity	NPD4538	Approved
0.7832	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD5177	Phase 3
0.7795	Intermediate Similarity	NPD290	Approved
0.7793	Intermediate Similarity	NPD7266	Discontinued
0.7793	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.7769	Intermediate Similarity	NPD7843	Approved
0.7764	Intermediate Similarity	NPD7074	Phase 3
0.7756	Intermediate Similarity	NPD6234	Discontinued
0.7742	Intermediate Similarity	NPD3882	Suspended
0.7737	Intermediate Similarity	NPD2983	Phase 2
0.7737	Intermediate Similarity	NPD2982	Phase 2
0.7737	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6671	Approved
0.7702	Intermediate Similarity	NPD7054	Approved
0.7692	Intermediate Similarity	NPD6355	Discontinued
0.7692	Intermediate Similarity	NPD5735	Approved
0.7671	Intermediate Similarity	NPD5763	Approved
0.7671	Intermediate Similarity	NPD5762	Approved
0.7667	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD2981	Phase 2
0.7662	Intermediate Similarity	NPD37	Approved
0.7655	Intermediate Similarity	NPD5960	Phase 3
0.7655	Intermediate Similarity	NPD5588	Approved
0.7654	Intermediate Similarity	NPD7472	Approved
0.764	Intermediate Similarity	NPD3818	Discontinued
0.764	Intermediate Similarity	NPD7228	Approved
0.7635	Intermediate Similarity	NPD6331	Phase 2
0.7628	Intermediate Similarity	NPD4967	Phase 2
0.7628	Intermediate Similarity	NPD4966	Approved
0.7628	Intermediate Similarity	NPD4965	Approved
0.7625	Intermediate Similarity	NPD2489	Approved
0.7625	Intermediate Similarity	NPD27	Approved
0.7606	Intermediate Similarity	NPD6798	Discontinued
0.76	Intermediate Similarity	NPD1511	Approved
0.7593	Intermediate Similarity	NPD5844	Phase 1
0.7591	Intermediate Similarity	NPD3705	Approved
0.7584	Intermediate Similarity	NPD2677	Approved
0.7574	Intermediate Similarity	NPD5846	Approved
0.7574	Intermediate Similarity	NPD6516	Phase 2
0.7571	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6584	Phase 3
0.7569	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD5124	Phase 1
0.7568	Intermediate Similarity	NPD3060	Approved
0.7562	Intermediate Similarity	NPD2970	Approved
0.7562	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2969	Approved
0.755	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD7095	Approved
0.7533	Intermediate Similarity	NPD5058	Phase 3
0.7517	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4628	Phase 3
0.7517	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD1512	Approved
0.75	Intermediate Similarity	NPD1357	Approved
0.75	Intermediate Similarity	NPD3051	Approved
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7484	Intermediate Similarity	NPD5494	Approved
0.7483	Intermediate Similarity	NPD6100	Approved
0.7483	Intermediate Similarity	NPD7213	Phase 3
0.7483	Intermediate Similarity	NPD7212	Phase 2
0.7483	Intermediate Similarity	NPD6099	Approved
0.7483	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7251	Discontinued
0.7452	Intermediate Similarity	NPD2560	Approved
0.7452	Intermediate Similarity	NPD3817	Phase 2
0.7452	Intermediate Similarity	NPD2563	Approved
0.745	Intermediate Similarity	NPD4237	Approved
0.745	Intermediate Similarity	NPD4236	Phase 3
0.745	Intermediate Similarity	NPD1652	Phase 2
0.745	Intermediate Similarity	NPD4162	Approved
0.7434	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7447	Phase 1
0.7432	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4380	Phase 2
0.7415	Intermediate Similarity	NPD7033	Discontinued
0.741	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7808	Phase 3
0.7402	Intermediate Similarity	NPD291	Approved
0.74	Intermediate Similarity	NPD3892	Phase 2
0.7394	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6071	Discontinued
0.7389	Intermediate Similarity	NPD1465	Phase 2
0.7386	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1549	Phase 2
0.7383	Intermediate Similarity	NPD2424	Discontinued
0.7379	Intermediate Similarity	NPD4140	Approved
0.7379	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2238	Phase 2
0.7376	Intermediate Similarity	NPD2797	Approved
0.7368	Intermediate Similarity	NPD1774	Approved
0.7368	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7313	Approved
0.7365	Intermediate Similarity	NPD7311	Approved
0.7365	Intermediate Similarity	NPD7310	Approved
0.7365	Intermediate Similarity	NPD2161	Phase 2
0.7365	Intermediate Similarity	NPD7312	Approved
0.7358	Intermediate Similarity	NPD7075	Discontinued
0.7358	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6582	Phase 2
0.7357	Intermediate Similarity	NPD6583	Phase 3
0.7357	Intermediate Similarity	NPD5327	Phase 3
0.7355	Intermediate Similarity	NPD4005	Discontinued
0.7353	Intermediate Similarity	NPD5536	Phase 2
0.7351	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD422	Phase 1
0.7337	Intermediate Similarity	NPD4663	Approved
0.7321	Intermediate Similarity	NPD8054	Approved
0.7321	Intermediate Similarity	NPD7309	Approved
0.7321	Intermediate Similarity	NPD8053	Approved
0.732	Intermediate Similarity	NPD4123	Phase 3
0.7315	Intermediate Similarity	NPD1375	Discontinued
0.7315	Intermediate Similarity	NPD3540	Phase 1
0.731	Intermediate Similarity	NPD6233	Phase 2
0.7308	Intermediate Similarity	NPD4678	Approved
0.7308	Intermediate Similarity	NPD4675	Approved
0.7308	Intermediate Similarity	NPD968	Approved
0.7305	Intermediate Similarity	NPD7549	Discontinued
0.7286	Intermediate Similarity	NPD1608	Approved
0.7286	Intermediate Similarity	NPD2231	Phase 2
0.7286	Intermediate Similarity	NPD2235	Phase 2
0.7285	Intermediate Similarity	NPD4535	Phase 3
0.7285	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6653	Approved
0.7278	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8455	Phase 2
0.7273	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD52	Approved
0.7273	Intermediate Similarity	NPD7526	Approved
0.7262	Intermediate Similarity	NPD4577	Approved
0.7262	Intermediate Similarity	NPD4578	Approved
0.7261	Intermediate Similarity	NPD6072	Discontinued
0.7255	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7041	Phase 2
0.7254	Intermediate Similarity	NPD3094	Phase 2
0.7248	Intermediate Similarity	NPD3539	Phase 1
0.7244	Intermediate Similarity	NPD3020	Approved
0.7241	Intermediate Similarity	NPD5109	Approved
0.7241	Intermediate Similarity	NPD5111	Phase 2
0.7241	Intermediate Similarity	NPD3268	Approved
0.7241	Intermediate Similarity	NPD5110	Phase 2
0.7239	Intermediate Similarity	NPD5535	Approved
0.7237	Intermediate Similarity	NPD6190	Approved
0.7237	Intermediate Similarity	NPD5241	Discontinued
0.7233	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7097	Phase 1
0.7222	Intermediate Similarity	NPD8127	Discontinued
0.7214	Intermediate Similarity	NPD3092	Approved
0.7211	Intermediate Similarity	NPD3657	Discovery
0.7211	Intermediate Similarity	NPD4340	Discontinued
0.7208	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7906	Approved
0.7192	Intermediate Similarity	NPD2674	Phase 3

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