NPASS Compound

Structure

NPC474639 OpenBabel07101719522D 24 26 0 0 1 0 0 0 0 0999 V2000 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 17 1 0 0 0 0 8 24 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 24 1 0 0 0 0 16 17 1 6 0 0 0 16 23 1 0 0 0 0 17 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.11
Volume:	322.632
LogP:	1.477
LogD:	1.088
LogS:	-3.16
# Rotatable Bonds:	3
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.54
Synthetic Accessibility Score:	3.763
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.138
MDCK Permeability:	8.110882845357992e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.324
Human Intestinal Absorption (HIA):	0.564
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	95.76126861572266%
Volume Distribution (VD):	0.536
Pgp-substrate:	6.01639986038208%

ADMET: Metabolism

CYP1A2-inhibitor:	0.142
CYP1A2-substrate:	0.429
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.243
CYP2C9-substrate:	0.471
CYP2D6-inhibitor:	0.108
CYP2D6-substrate:	0.336
CYP3A4-inhibitor:	0.159
CYP3A4-substrate:	0.235

ADMET: Excretion

Clearance (CL):	15.814
Half-life (T1/2):	0.883

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.1
Drug-inuced Liver Injury (DILI):	0.413
AMES Toxicity:	0.79
Rat Oral Acute Toxicity:	0.467
Maximum Recommended Daily Dose:	0.654
Skin Sensitization:	0.96
Carcinogencity:	0.341
Eye Corrosion:	0.003
Eye Irritation:	0.915
Respiratory Toxicity:	0.212

Download Data

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

Natural Product: NPC474639

Natural Product ID:	NPC474639
*Common Name:**	4-O-Methylhematoxylol
IUPAC Name:	(3R,4S)-3-[(3,4-dihydroxyphenyl)methyl]-4-methoxy-2,4-dihydrochromene-3,7,8-triol
Synonyms:	4-O-Methylhematoxylol
Standard InCHIKey:	ZWLRTODWEJCVRS-DLBZAZTESA-N
Standard InCHI:	InChI=1S/C17H18O7/c1-23-16-10-3-5-12(19)14(21)15(10)24-8-17(16,22)7-9-2-4-11(18)13(20)6-9/h2-6,16,18-22H,7-8H2,1H3/t16-,17+/m0/s1
SMILES:	CO[C@H]1c2ccc(c(c2OC[C@]1(O)Cc1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477769
PubChem CID:	24949853
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans

*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
NPO32846	heamatoxylon campechianum	Species	n.a.	n.a.	stems	XiShuangBanNa, Yunnan Province, China	2005-Sep	PMID[18610999]

☑ 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
Others	7

Activity Type	# Activity
Individual Protein	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	Inhibition	=	25.7	%	PMID[551701]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	Inhibition	=	86.2	%	PMID[551701]
NPT1479	Individual Protein	Stem cell growth factor receptor	Homo sapiens	Inhibition	=	66.1	%	PMID[551701]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	Inhibition	=	54.5	%	PMID[551701]
NPT1480	Individual Protein	Fibroblast growth factor receptor 1	Homo sapiens	Inhibition	=	93.3	%	PMID[551701]
NPT1481	Individual Protein	Fibroblast growth factor receptor 2	Homo sapiens	Inhibition	=	60.3	%	PMID[551701]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	Inhibition	=	79.5	%	PMID[551701]

☑ 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 NPC474639 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	426
0.1-0.2	1658
0.2-0.3	4952
0.3-0.4	12473
0.4-0.5	5206
0.5-0.6	4029
0.6-0.7	5879
0.7-0.8	5987
0.8-0.85	1101
0.85-0.9	615
0.9-0.95	309
0.95-1	62

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC227503
1.0	High Similarity	NPC230734
0.9922	High Similarity	NPC470356
0.9922	High Similarity	NPC151224
0.9922	High Similarity	NPC94750
0.9922	High Similarity	NPC112939
0.9922	High Similarity	NPC121812
0.9922	High Similarity	NPC112246
0.9922	High Similarity	NPC474206
0.9846	High Similarity	NPC302701
0.9846	High Similarity	NPC306441
0.9846	High Similarity	NPC16435
0.9846	High Similarity	NPC269091
0.9771	High Similarity	NPC326797
0.9771	High Similarity	NPC474282
0.9771	High Similarity	NPC107551
0.9771	High Similarity	NPC103976
0.9771	High Similarity	NPC176051
0.9771	High Similarity	NPC211549
0.9771	High Similarity	NPC102904
0.9769	High Similarity	NPC164787
0.9769	High Similarity	NPC47398
0.9769	High Similarity	NPC260898
0.9769	High Similarity	NPC61946
0.9769	High Similarity	NPC234333
0.9767	High Similarity	NPC11060
0.9695	High Similarity	NPC270456
0.9695	High Similarity	NPC162659
0.9695	High Similarity	NPC248727
0.9695	High Similarity	NPC265433
0.9692	High Similarity	NPC317380
0.969	High Similarity	NPC127624
0.969	High Similarity	NPC86655
0.969	High Similarity	NPC202762
0.9624	High Similarity	NPC309124
0.9624	High Similarity	NPC184797
0.9621	High Similarity	NPC276490
0.9618	High Similarity	NPC473413
0.9615	High Similarity	NPC263064
0.9615	High Similarity	NPC229442
0.9615	High Similarity	NPC168059
0.9615	High Similarity	NPC475840
0.9556	High Similarity	NPC81638
0.9552	High Similarity	NPC471389
0.9549	High Similarity	NPC232164
0.9549	High Similarity	NPC319647
0.9549	High Similarity	NPC127218
0.9549	High Similarity	NPC25966
0.9549	High Similarity	NPC260741
0.9549	High Similarity	NPC236306
0.9549	High Similarity	NPC70682
0.9549	High Similarity	NPC473739
0.9549	High Similarity	NPC245207
0.9545	High Similarity	NPC470802
0.9545	High Similarity	NPC472334
0.9545	High Similarity	NPC472336
0.9545	High Similarity	NPC234952
0.9542	High Similarity	NPC170694
0.9538	High Similarity	NPC219876
0.9538	High Similarity	NPC61477
0.9538	High Similarity	NPC78770
0.9538	High Similarity	NPC15658
0.9538	High Similarity	NPC253105
0.9538	High Similarity	NPC126029
0.9538	High Similarity	NPC261619
0.9538	High Similarity	NPC185604
0.9538	High Similarity	NPC201587
0.9481	High Similarity	NPC107161
0.9481	High Similarity	NPC204347
0.9481	High Similarity	NPC475891
0.9481	High Similarity	NPC2613
0.9481	High Similarity	NPC59841
0.9478	High Similarity	NPC22317
0.947	High Similarity	NPC472337
0.947	High Similarity	NPC195022
0.9462	High Similarity	NPC268342
0.9462	High Similarity	NPC42760
0.9462	High Similarity	NPC268266
0.9462	High Similarity	NPC220825
0.9462	High Similarity	NPC472597
0.9407	High Similarity	NPC35216
0.9407	High Similarity	NPC247291
0.9403	High Similarity	NPC32630
0.9403	High Similarity	NPC471388
0.9398	High Similarity	NPC173660
0.9394	High Similarity	NPC478085
0.9394	High Similarity	NPC106215
0.9389	High Similarity	NPC16208
0.9389	High Similarity	NPC184447
0.9389	High Similarity	NPC35932
0.9389	High Similarity	NPC470752
0.9389	High Similarity	NPC160991
0.9389	High Similarity	NPC7903
0.9385	High Similarity	NPC472338
0.9385	High Similarity	NPC91291
0.938	High Similarity	NPC87224
0.938	High Similarity	NPC31707
0.938	High Similarity	NPC46274
0.938	High Similarity	NPC226331
0.938	High Similarity	NPC222572
0.9348	High Similarity	NPC233980
0.9343	High Similarity	NPC12641
0.9343	High Similarity	NPC473108
0.9343	High Similarity	NPC280092
0.9343	High Similarity	NPC50250
0.9343	High Similarity	NPC45257
0.9343	High Similarity	NPC93323
0.9333	High Similarity	NPC259519
0.9333	High Similarity	NPC254759
0.9333	High Similarity	NPC160283
0.9333	High Similarity	NPC27495
0.9323	High Similarity	NPC134968
0.9318	High Similarity	NPC36661
0.9313	High Similarity	NPC309787
0.9308	High Similarity	NPC190629
0.9308	High Similarity	NPC273295
0.9308	High Similarity	NPC202582
0.9308	High Similarity	NPC5851
0.9308	High Similarity	NPC3439
0.9308	High Similarity	NPC210623
0.9308	High Similarity	NPC86030
0.9308	High Similarity	NPC218856
0.9308	High Similarity	NPC470258
0.9308	High Similarity	NPC170844
0.9308	High Similarity	NPC226788
0.9308	High Similarity	NPC476968
0.9308	High Similarity	NPC212015
0.9308	High Similarity	NPC222004
0.9308	High Similarity	NPC285339
0.9302	High Similarity	NPC324112
0.9302	High Similarity	NPC282000
0.9302	High Similarity	NPC169474
0.9302	High Similarity	NPC210355
0.9302	High Similarity	NPC74817
0.9302	High Similarity	NPC159968
0.9302	High Similarity	NPC293054
0.9302	High Similarity	NPC246620
0.9302	High Similarity	NPC5447
0.9302	High Similarity	NPC250432
0.9302	High Similarity	NPC82679
0.9302	High Similarity	NPC124452
0.9302	High Similarity	NPC236791
0.9281	High Similarity	NPC474397
0.9281	High Similarity	NPC21776
0.9281	High Similarity	NPC16269
0.9275	High Similarity	NPC475096
0.927	High Similarity	NPC47633
0.927	High Similarity	NPC85264
0.927	High Similarity	NPC102044
0.9265	High Similarity	NPC87725
0.9265	High Similarity	NPC178054
0.9265	High Similarity	NPC265075
0.9265	High Similarity	NPC263261
0.9259	High Similarity	NPC22517
0.9259	High Similarity	NPC292882
0.9248	High Similarity	NPC310854
0.9237	High Similarity	NPC234488
0.9237	High Similarity	NPC299221
0.9237	High Similarity	NPC214860
0.9237	High Similarity	NPC311680
0.9237	High Similarity	NPC51840
0.9231	High Similarity	NPC252307
0.9231	High Similarity	NPC245826
0.9231	High Similarity	NPC470213
0.9231	High Similarity	NPC186843
0.9231	High Similarity	NPC72529
0.9231	High Similarity	NPC206615
0.9231	High Similarity	NPC474178
0.9231	High Similarity	NPC98631
0.9225	High Similarity	NPC44748
0.9225	High Similarity	NPC78974
0.9225	High Similarity	NPC214406
0.9225	High Similarity	NPC223136
0.9225	High Similarity	NPC28730
0.9225	High Similarity	NPC103823
0.9225	High Similarity	NPC18924
0.9214	High Similarity	NPC473876
0.9209	High Similarity	NPC87794
0.9209	High Similarity	NPC190714
0.9209	High Similarity	NPC125755
0.9209	High Similarity	NPC211758
0.9209	High Similarity	NPC99515
0.9203	High Similarity	NPC171932
0.9203	High Similarity	NPC63879
0.9203	High Similarity	NPC28440
0.9197	High Similarity	NPC189115
0.9197	High Similarity	NPC475084
0.9191	High Similarity	NPC262189
0.9191	High Similarity	NPC266197
0.9191	High Similarity	NPC291101
0.9185	High Similarity	NPC474390
0.9179	High Similarity	NPC256262
0.9173	High Similarity	NPC158331
0.9167	High Similarity	NPC469613
0.9167	High Similarity	NPC474017
0.9167	High Similarity	NPC103799
0.9167	High Similarity	NPC30043
0.9167	High Similarity	NPC162801
0.9167	High Similarity	NPC470095
0.9167	High Similarity	NPC469625

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 NPC474639 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	890
0.2-0.3	1933
0.3-0.4	2696
0.4-0.5	1529
0.5-0.6	881
0.6-0.7	656
0.7-0.8	165
0.8-0.85	12
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9538	High Similarity	NPD1612	Clinical (unspecified phase)
0.9538	High Similarity	NPD1613	Approved
0.938	High Similarity	NPD1529	Clinical (unspecified phase)
0.9308	High Similarity	NPD3027	Phase 3
0.9302	High Similarity	NPD1530	Clinical (unspecified phase)
0.8657	High Similarity	NPD4908	Phase 1
0.8639	High Similarity	NPD1934	Approved
0.855	High Similarity	NPD1610	Phase 2
0.8529	High Similarity	NPD4907	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD1548	Phase 1
0.8321	Intermediate Similarity	NPD4625	Phase 3
0.8309	Intermediate Similarity	NPD2861	Phase 2
0.8284	Intermediate Similarity	NPD4749	Approved
0.8243	Intermediate Similarity	NPD1653	Approved
0.8224	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD2801	Approved
0.8205	Intermediate Similarity	NPD6166	Phase 2
0.8205	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD3018	Phase 2
0.8129	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD2983	Phase 2
0.8015	Intermediate Similarity	NPD2982	Phase 2
0.8	Intermediate Similarity	NPD7074	Phase 3
0.7987	Intermediate Similarity	NPD3882	Suspended
0.7984	Intermediate Similarity	NPD228	Approved
0.7973	Intermediate Similarity	NPD1511	Approved
0.7945	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD2981	Phase 2
0.7937	Intermediate Similarity	NPD7054	Approved
0.7888	Intermediate Similarity	NPD7472	Approved
0.7885	Intermediate Similarity	NPD6234	Discontinued
0.7879	Intermediate Similarity	NPD6671	Approved
0.7875	Intermediate Similarity	NPD3818	Discontinued
0.7868	Intermediate Similarity	NPD1091	Approved
0.7867	Intermediate Similarity	NPD1512	Approved
0.7863	Intermediate Similarity	NPD5283	Phase 1
0.7823	Intermediate Similarity	NPD6674	Discontinued
0.7806	Intermediate Similarity	NPD3817	Phase 2
0.7762	Intermediate Similarity	NPD1558	Phase 1
0.7762	Intermediate Similarity	NPD4060	Phase 1
0.7754	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7213	Phase 3
0.7733	Intermediate Similarity	NPD7212	Phase 2
0.773	Intermediate Similarity	NPD6797	Phase 2
0.7724	Intermediate Similarity	NPD4536	Approved
0.7724	Intermediate Similarity	NPD4538	Approved
0.7724	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5844	Phase 1
0.7708	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5124	Phase 1
0.7703	Intermediate Similarity	NPD1652	Phase 2
0.7687	Intermediate Similarity	NPD7266	Discontinued
0.7687	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7251	Discontinued
0.7682	Intermediate Similarity	NPD7447	Phase 1
0.7677	Intermediate Similarity	NPD37	Approved
0.7673	Intermediate Similarity	NPD7199	Phase 2
0.7662	Intermediate Similarity	NPD4380	Phase 2
0.7662	Intermediate Similarity	NPD4678	Approved
0.7662	Intermediate Similarity	NPD4675	Approved
0.7654	Intermediate Similarity	NPD7228	Approved
0.7643	Intermediate Similarity	NPD4966	Approved
0.7643	Intermediate Similarity	NPD4965	Approved
0.7643	Intermediate Similarity	NPD4967	Phase 2
0.7639	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3620	Phase 2
0.7636	Intermediate Similarity	NPD7808	Phase 3
0.7636	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1549	Phase 2
0.7628	Intermediate Similarity	NPD1465	Phase 2
0.7622	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6100	Approved
0.7619	Intermediate Similarity	NPD6099	Approved
0.7615	Intermediate Similarity	NPD2684	Approved
0.761	Intermediate Similarity	NPD5494	Approved
0.7609	Intermediate Similarity	NPD422	Phase 1
0.76	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7075	Discontinued
0.7595	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5177	Phase 3
0.7578	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8651	Approved
0.7568	Intermediate Similarity	NPD3540	Phase 1
0.7566	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD3022	Approved
0.7557	Intermediate Similarity	NPD3021	Approved
0.7551	Intermediate Similarity	NPD5588	Approved
0.7551	Intermediate Similarity	NPD5960	Phase 3
0.755	Intermediate Similarity	NPD5058	Phase 3
0.7538	Intermediate Similarity	NPD290	Approved
0.753	Intermediate Similarity	NPD7549	Discontinued
0.7519	Intermediate Similarity	NPD7843	Approved
0.7516	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3539	Phase 1
0.75	Intermediate Similarity	NPD6798	Discontinued
0.7484	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD3705	Approved
0.7481	Intermediate Similarity	NPD7157	Approved
0.7468	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6584	Phase 3
0.744	Intermediate Similarity	NPD8054	Approved
0.744	Intermediate Similarity	NPD8053	Approved
0.7432	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD7095	Approved
0.7417	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6232	Discontinued
0.7403	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2424	Discontinued
0.7389	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2796	Approved
0.7376	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4005	Discontinued
0.7368	Intermediate Similarity	NPD2677	Approved
0.7368	Intermediate Similarity	NPD6190	Approved
0.7365	Intermediate Similarity	NPD6559	Discontinued
0.7358	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3060	Approved
0.7347	Intermediate Similarity	NPD6355	Discontinued
0.7338	Intermediate Similarity	NPD4123	Phase 3
0.7338	Intermediate Similarity	NPD6516	Phase 2
0.7338	Intermediate Similarity	NPD5846	Approved
0.7333	Intermediate Similarity	NPD1375	Discontinued
0.7329	Intermediate Similarity	NPD6233	Phase 2
0.7328	Intermediate Similarity	NPD968	Approved
0.7315	Intermediate Similarity	NPD1510	Phase 2
0.7315	Intermediate Similarity	NPD7033	Discontinued
0.731	Intermediate Similarity	NPD7906	Approved
0.7303	Intermediate Similarity	NPD6331	Phase 2
0.7303	Intermediate Similarity	NPD3750	Approved
0.7303	Intermediate Similarity	NPD3892	Phase 2
0.7303	Intermediate Similarity	NPD7466	Approved
0.7301	Intermediate Similarity	NPD3787	Discontinued
0.7296	Intermediate Similarity	NPD7819	Suspended
0.7289	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD940	Approved
0.7287	Intermediate Similarity	NPD846	Approved
0.7279	Intermediate Similarity	NPD2238	Phase 2
0.7278	Intermediate Similarity	NPD4577	Approved
0.7278	Intermediate Similarity	NPD7313	Approved
0.7278	Intermediate Similarity	NPD7310	Approved
0.7278	Intermediate Similarity	NPD7312	Approved
0.7278	Intermediate Similarity	NPD4578	Approved
0.7278	Intermediate Similarity	NPD7311	Approved
0.7273	Intermediate Similarity	NPD7473	Discontinued
0.7273	Intermediate Similarity	NPD6799	Approved
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4357	Discontinued
0.7273	Intermediate Similarity	NPD1774	Approved
0.7266	Intermediate Similarity	NPD1357	Approved
0.7254	Intermediate Similarity	NPD6582	Phase 2
0.7254	Intermediate Similarity	NPD6583	Phase 3
0.7251	Intermediate Similarity	NPD4663	Approved
0.725	Intermediate Similarity	NPD5402	Approved
0.7248	Intermediate Similarity	NPD7097	Phase 1
0.7246	Intermediate Similarity	NPD5536	Phase 2
0.7241	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6959	Discontinued
0.7237	Intermediate Similarity	NPD4162	Approved
0.7237	Intermediate Similarity	NPD4237	Approved
0.7237	Intermediate Similarity	NPD4236	Phase 3
0.7235	Intermediate Similarity	NPD7309	Approved
0.7233	Intermediate Similarity	NPD6801	Discontinued
0.723	Intermediate Similarity	NPD230	Phase 1
0.723	Intermediate Similarity	NPD5735	Approved
0.7226	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5762	Approved
0.7219	Intermediate Similarity	NPD5763	Approved
0.7212	Intermediate Similarity	NPD27	Approved
0.7212	Intermediate Similarity	NPD2489	Approved
0.7209	Intermediate Similarity	NPD1242	Phase 1
0.7208	Intermediate Similarity	NPD7124	Phase 2
0.7203	Intermediate Similarity	NPD6696	Suspended
0.7193	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4535	Phase 3
0.719	Intermediate Similarity	NPD4110	Phase 3
0.719	Intermediate Similarity	NPD4628	Phase 3
0.7179	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6072	Discontinued
0.717	Intermediate Similarity	NPD7411	Suspended
0.7164	Intermediate Similarity	NPD4750	Phase 3
0.7163	Intermediate Similarity	NPD3496	Discontinued
0.7162	Intermediate Similarity	NPD1240	Approved
0.7162	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7240	Approved
0.7154	Intermediate Similarity	NPD291	Approved
0.7152	Intermediate Similarity	NPD2969	Approved
0.7152	Intermediate Similarity	NPD2970	Approved
0.7152	Intermediate Similarity	NPD6032	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