NPASS Compound

Structure

NPC302701 OpenBabel07101718332D 23 25 0 0 1 0 0 0 0 0999 V2000 0.5176 1.9319 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 0.7765 2.8978 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 2.1907 1.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 0.2588 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 1.2247 1.2247 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 1.7424 3.1566 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 2.4495 2.4495 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 2 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 2.0012 4.1225 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 3.4154 2.7083 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1305 -0.9914 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 3 2 0 0 0 0 1 8 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 16 1 0 0 0 0 7 16 1 0 0 0 0 7 23 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 6 0 0 0 15 21 1 0 0 0 0 16 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.09
Volume:	305.336
LogP:	0.708
LogD:	-0.004
LogS:	-3.227
# Rotatable Bonds:	2
TPSA:	130.61
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.453
Synthetic Accessibility Score:	3.674
Fsp3:	0.25
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:	-6.126
MDCK Permeability:	4.8835427151061594e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.151
Human Intestinal Absorption (HIA):	0.799
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	96.20028686523438%
Volume Distribution (VD):	0.552
Pgp-substrate:	4.051826000213623%

ADMET: Metabolism

CYP1A2-inhibitor:	0.513
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.274
CYP2C9-substrate:	0.642
CYP2D6-inhibitor:	0.12
CYP2D6-substrate:	0.322
CYP3A4-inhibitor:	0.134
CYP3A4-substrate:	0.121

ADMET: Excretion

Clearance (CL):	13.541
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.33
AMES Toxicity:	0.788
Rat Oral Acute Toxicity:	0.585
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.945
Carcinogencity:	0.093
Eye Corrosion:	0.003
Eye Irritation:	0.912
Respiratory Toxicity:	0.064

Download Data

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

Natural Product: NPC302701

Natural Product ID:	NPC302701
*Common Name:**	Epihematoxylol
IUPAC Name:	(3R,4R)-3-[(3,4-dihydroxyphenyl)methyl]-2,4-dihydrochromene-3,4,7,8-tetrol
Synonyms:	Epihematoxylol
Standard InCHIKey:	FUVGPYLFLOWRMC-HZPDHXFCSA-N
Standard InCHI:	InChI=1S/C16H16O7/c17-10-3-1-8(5-12(10)19)6-16(22)7-23-14-9(15(16)21)2-4-11(18)13(14)20/h1-5,15,17-22H,6-7H2/t15-,16-/m1/s1
SMILES:	c1cc(c(cc1C[C@]1(COc2c(ccc(c2O)O)[C@H]1O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478611
PubChem CID:	24949852
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
IC50	5
Others	7

Activity Type	# Activity
Individual Protein	12

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	=	91.0	%	PMID[468684]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	Inhibition	=	95.3	%	PMID[468684]
NPT1479	Individual Protein	Stem cell growth factor receptor	Homo sapiens	Inhibition	=	93.2	%	PMID[468684]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	Inhibition	=	66.6	%	PMID[468684]
NPT1480	Individual Protein	Fibroblast growth factor receptor 1	Homo sapiens	Inhibition	=	97.5	%	PMID[468684]
NPT1481	Individual Protein	Fibroblast growth factor receptor 2	Homo sapiens	Inhibition	=	84.9	%	PMID[468684]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	Inhibition	=	96.2	%	PMID[468684]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	IC50	=	360.0	nM	PMID[468684]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	=	360.0	nM	PMID[468684]
NPT1480	Individual Protein	Fibroblast growth factor receptor 1	Homo sapiens	IC50	=	560.0	nM	PMID[468684]
NPT1479	Individual Protein	Stem cell growth factor receptor	Homo sapiens	IC50	=	700.0	nM	PMID[468684]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	IC50	=	2100.0	nM	PMID[468684]

☑ 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 NPC302701 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	484
0.1-0.2	1700
0.2-0.3	5153
0.3-0.4	12425
0.4-0.5	5109
0.5-0.6	4119
0.6-0.7	6006
0.7-0.8	5746
0.8-0.85	1065
0.85-0.9	568
0.9-0.95	274
0.95-1	48

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC269091
0.9922	High Similarity	NPC164787
0.9846	High Similarity	NPC227503
0.9846	High Similarity	NPC306441
0.9846	High Similarity	NPC474639
0.9846	High Similarity	NPC16435
0.9846	High Similarity	NPC230734
0.9769	High Similarity	NPC94750
0.9769	High Similarity	NPC474206
0.9769	High Similarity	NPC470356
0.9769	High Similarity	NPC47398
0.9769	High Similarity	NPC121812
0.9769	High Similarity	NPC151224
0.9769	High Similarity	NPC260898
0.9769	High Similarity	NPC112939
0.9769	High Similarity	NPC112246
0.9769	High Similarity	NPC61946
0.9769	High Similarity	NPC234333
0.969	High Similarity	NPC261619
0.969	High Similarity	NPC15658
0.969	High Similarity	NPC78770
0.969	High Similarity	NPC126029
0.969	High Similarity	NPC185604
0.969	High Similarity	NPC61477
0.969	High Similarity	NPC219876
0.9621	High Similarity	NPC474282
0.9621	High Similarity	NPC176051
0.9621	High Similarity	NPC103976
0.9621	High Similarity	NPC211549
0.9621	High Similarity	NPC102904
0.9621	High Similarity	NPC107551
0.9621	High Similarity	NPC326797
0.9615	High Similarity	NPC11060
0.9615	High Similarity	NPC263064
0.9615	High Similarity	NPC475840
0.9612	High Similarity	NPC268266
0.9612	High Similarity	NPC42760
0.9612	High Similarity	NPC268342
0.9612	High Similarity	NPC220825
0.9552	High Similarity	NPC471389
0.9545	High Similarity	NPC470802
0.9545	High Similarity	NPC472334
0.9545	High Similarity	NPC162659
0.9545	High Similarity	NPC248727
0.9545	High Similarity	NPC270456
0.9545	High Similarity	NPC472336
0.9545	High Similarity	NPC265433
0.9542	High Similarity	NPC317380
0.9542	High Similarity	NPC170694
0.9538	High Similarity	NPC86655
0.9538	High Similarity	NPC127624
0.9538	High Similarity	NPC253105
0.9538	High Similarity	NPC470752
0.9538	High Similarity	NPC202762
0.9538	High Similarity	NPC201587
0.9478	High Similarity	NPC309124
0.9478	High Similarity	NPC184797
0.9474	High Similarity	NPC276490
0.947	High Similarity	NPC473413
0.947	High Similarity	NPC472337
0.9466	High Similarity	NPC229442
0.9466	High Similarity	NPC168059
0.9462	High Similarity	NPC309787
0.9462	High Similarity	NPC472597
0.9412	High Similarity	NPC81638
0.9407	High Similarity	NPC178054
0.9403	High Similarity	NPC70682
0.9403	High Similarity	NPC260741
0.9403	High Similarity	NPC232164
0.9403	High Similarity	NPC473739
0.9403	High Similarity	NPC25966
0.9403	High Similarity	NPC127218
0.9403	High Similarity	NPC236306
0.9403	High Similarity	NPC471388
0.9403	High Similarity	NPC319647
0.9403	High Similarity	NPC245207
0.9398	High Similarity	NPC234952
0.9394	High Similarity	NPC478085
0.9389	High Similarity	NPC16208
0.9389	High Similarity	NPC184447
0.9389	High Similarity	NPC35932
0.9389	High Similarity	NPC160991
0.9389	High Similarity	NPC7903
0.9385	High Similarity	NPC472338
0.9385	High Similarity	NPC91291
0.938	High Similarity	NPC46274
0.938	High Similarity	NPC226331
0.938	High Similarity	NPC72529
0.9343	High Similarity	NPC171932
0.9343	High Similarity	NPC28440
0.9338	High Similarity	NPC475891
0.9338	High Similarity	NPC107161
0.9338	High Similarity	NPC204347
0.9338	High Similarity	NPC59841
0.9338	High Similarity	NPC2613
0.9333	High Similarity	NPC22317
0.9328	High Similarity	NPC474390
0.9323	High Similarity	NPC195022
0.9308	High Similarity	NPC190629
0.9308	High Similarity	NPC5851
0.9308	High Similarity	NPC218856
0.9308	High Similarity	NPC202582
0.9308	High Similarity	NPC86030
0.9308	High Similarity	NPC3439
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	NPC273295
0.9308	High Similarity	NPC210623
0.9308	High Similarity	NPC222004
0.9308	High Similarity	NPC285339
0.9302	High Similarity	NPC5447
0.9302	High Similarity	NPC250432
0.9281	High Similarity	NPC474397
0.9275	High Similarity	NPC475096
0.9265	High Similarity	NPC87725
0.9265	High Similarity	NPC263261
0.9265	High Similarity	NPC35216
0.9265	High Similarity	NPC247291
0.9265	High Similarity	NPC469661
0.9259	High Similarity	NPC32630
0.9259	High Similarity	NPC22517
0.9254	High Similarity	NPC173660
0.9248	High Similarity	NPC310854
0.9248	High Similarity	NPC106215
0.9231	High Similarity	NPC222572
0.9231	High Similarity	NPC31707
0.9231	High Similarity	NPC245826
0.9231	High Similarity	NPC470213
0.9231	High Similarity	NPC186843
0.9231	High Similarity	NPC206615
0.9231	High Similarity	NPC252307
0.9231	High Similarity	NPC474178
0.9231	High Similarity	NPC87224
0.9231	High Similarity	NPC98631
0.9214	High Similarity	NPC473876
0.9209	High Similarity	NPC190714
0.9209	High Similarity	NPC125755
0.9209	High Similarity	NPC233980
0.9209	High Similarity	NPC99515
0.9203	High Similarity	NPC473108
0.9203	High Similarity	NPC168579
0.9203	High Similarity	NPC50250
0.9203	High Similarity	NPC76176
0.9203	High Similarity	NPC138227
0.9203	High Similarity	NPC280092
0.9203	High Similarity	NPC93323
0.9203	High Similarity	NPC12641
0.9203	High Similarity	NPC45257
0.9203	High Similarity	NPC469313
0.9197	High Similarity	NPC189115
0.9197	High Similarity	NPC475084
0.9191	High Similarity	NPC160283
0.9191	High Similarity	NPC262189
0.9191	High Similarity	NPC254759
0.9191	High Similarity	NPC266197
0.9191	High Similarity	NPC27495
0.9191	High Similarity	NPC259519
0.9191	High Similarity	NPC291101
0.9179	High Similarity	NPC256262
0.9179	High Similarity	NPC134968
0.9173	High Similarity	NPC36661
0.9167	High Similarity	NPC469613
0.9167	High Similarity	NPC474017
0.9167	High Similarity	NPC103799
0.9167	High Similarity	NPC470095
0.9167	High Similarity	NPC469625
0.9167	High Similarity	NPC30043
0.9167	High Similarity	NPC470096
0.916	High Similarity	NPC469963
0.916	High Similarity	NPC469951
0.9154	High Similarity	NPC169474
0.9154	High Similarity	NPC474119
0.9154	High Similarity	NPC124452
0.9154	High Similarity	NPC163332
0.9154	High Similarity	NPC159968
0.9154	High Similarity	NPC74817
0.9154	High Similarity	NPC292056
0.9154	High Similarity	NPC111247
0.9154	High Similarity	NPC210355
0.9154	High Similarity	NPC236791
0.9154	High Similarity	NPC147821
0.9154	High Similarity	NPC246620
0.9154	High Similarity	NPC319625
0.9154	High Similarity	NPC118787
0.9154	High Similarity	NPC82679
0.9154	High Similarity	NPC183181
0.9154	High Similarity	NPC293054
0.9154	High Similarity	NPC41706
0.9154	High Similarity	NPC470699
0.9154	High Similarity	NPC324112
0.9154	High Similarity	NPC282000
0.9154	High Similarity	NPC242032
0.9147	High Similarity	NPC278552
0.9147	High Similarity	NPC207179
0.9147	High Similarity	NPC167571
0.9143	High Similarity	NPC21776
0.9143	High Similarity	NPC101376

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 NPC302701 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	413
0.1-0.2	870
0.2-0.3	2037
0.3-0.4	2664
0.4-0.5	1502
0.5-0.6	861
0.6-0.7	626
0.7-0.8	161
0.8-0.85	10
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.969	High Similarity	NPD1613	Approved
0.969	High Similarity	NPD1612	Clinical (unspecified phase)
0.938	High Similarity	NPD1529	Clinical (unspecified phase)
0.9308	High Similarity	NPD3027	Phase 3
0.9302	High Similarity	NPD1530	Clinical (unspecified phase)
0.855	High Similarity	NPD1610	Phase 2
0.8519	High Similarity	NPD4908	Phase 1
0.8514	High Similarity	NPD1934	Approved
0.8394	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD1548	Phase 1
0.8367	Intermediate Similarity	NPD1653	Approved
0.8333	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD2861	Phase 2
0.8224	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD6166	Phase 2
0.8205	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD4625	Phase 3
0.8148	Intermediate Similarity	NPD4749	Approved
0.8129	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD2801	Approved
0.8043	Intermediate Similarity	NPD3018	Phase 2
0.8	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD1091	Approved
0.7987	Intermediate Similarity	NPD3818	Discontinued
0.7973	Intermediate Similarity	NPD1511	Approved
0.7945	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7054	Approved
0.7888	Intermediate Similarity	NPD7472	Approved
0.7883	Intermediate Similarity	NPD2983	Phase 2
0.7883	Intermediate Similarity	NPD2982	Phase 2
0.7871	Intermediate Similarity	NPD3882	Suspended
0.7867	Intermediate Similarity	NPD1512	Approved
0.7846	Intermediate Similarity	NPD228	Approved
0.7823	Intermediate Similarity	NPD6674	Discontinued
0.781	Intermediate Similarity	NPD2981	Phase 2
0.7778	Intermediate Similarity	NPD4380	Phase 2
0.7771	Intermediate Similarity	NPD6234	Discontinued
0.7744	Intermediate Similarity	NPD6671	Approved
0.7744	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6797	Phase 2
0.7727	Intermediate Similarity	NPD5283	Phase 1
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
0.7707	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1652	Phase 2
0.7692	Intermediate Similarity	NPD3817	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
0.7677	Intermediate Similarity	NPD37	Approved
0.7673	Intermediate Similarity	NPD7199	Phase 2
0.7671	Intermediate Similarity	NPD5588	Approved
0.7671	Intermediate Similarity	NPD5960	Phase 3
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	NPD3620	Phase 2
0.7639	Intermediate Similarity	NPD4060	Phase 1
0.7639	Intermediate Similarity	NPD1558	Phase 1
0.7639	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7808	Phase 3
0.7635	Intermediate Similarity	NPD1549	Phase 2
0.7628	Intermediate Similarity	NPD1465	Phase 2
0.7626	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7213	Phase 3
0.7616	Intermediate Similarity	NPD7212	Phase 2
0.7615	Intermediate Similarity	NPD2684	Approved
0.7595	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5177	Phase 3
0.7571	Intermediate Similarity	NPD8651	Approved
0.7566	Intermediate Similarity	NPD7447	Phase 1
0.755	Intermediate Similarity	NPD5058	Phase 3
0.7548	Intermediate Similarity	NPD4675	Approved
0.7548	Intermediate Similarity	NPD4678	Approved
0.7538	Intermediate Similarity	NPD290	Approved
0.7519	Intermediate Similarity	NPD7843	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD5494	Approved
0.7484	Intermediate Similarity	NPD7075	Discontinued
0.7483	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6190	Approved
0.7482	Intermediate Similarity	NPD422	Phase 1
0.7481	Intermediate Similarity	NPD7157	Approved
0.7469	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD5846	Approved
0.7464	Intermediate Similarity	NPD6516	Phase 2
0.7451	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3540	Phase 1
0.7425	Intermediate Similarity	NPD7549	Discontinued
0.7424	Intermediate Similarity	NPD3022	Approved
0.7424	Intermediate Similarity	NPD3021	Approved
0.7417	Intermediate Similarity	NPD3892	Phase 2
0.7407	Intermediate Similarity	NPD3787	Discontinued
0.7405	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2424	Discontinued
0.7383	Intermediate Similarity	NPD3539	Phase 1
0.7379	Intermediate Similarity	NPD6798	Discontinued
0.7372	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4005	Discontinued
0.7368	Intermediate Similarity	NPD2677	Approved
0.7365	Intermediate Similarity	NPD6559	Discontinued
0.7358	Intermediate Similarity	NPD5402	Approved
0.7357	Intermediate Similarity	NPD3705	Approved
0.7353	Intermediate Similarity	NPD4663	Approved
0.7351	Intermediate Similarity	NPD3060	Approved
0.7343	Intermediate Similarity	NPD6584	Phase 3
0.7338	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8054	Approved
0.7337	Intermediate Similarity	NPD8053	Approved
0.7328	Intermediate Similarity	NPD968	Approved
0.7315	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7033	Discontinued
0.7315	Intermediate Similarity	NPD1510	Phase 2
0.731	Intermediate Similarity	NPD7095	Approved
0.7303	Intermediate Similarity	NPD3750	Approved
0.7303	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6232	Discontinued
0.729	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2238	Phase 2
0.7278	Intermediate Similarity	NPD4577	Approved
0.7278	Intermediate Similarity	NPD4578	Approved
0.7278	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1774	Approved
0.7267	Intermediate Similarity	NPD2796	Approved
0.7266	Intermediate Similarity	NPD1357	Approved
0.7254	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5403	Approved
0.7237	Intermediate Similarity	NPD4237	Approved
0.7237	Intermediate Similarity	NPD4236	Phase 3
0.7237	Intermediate Similarity	NPD4162	Approved
0.7233	Intermediate Similarity	NPD6801	Discontinued
0.723	Intermediate Similarity	NPD5735	Approved
0.723	Intermediate Similarity	NPD6355	Discontinued
0.7229	Intermediate Similarity	NPD3751	Discontinued
0.7226	Intermediate Similarity	NPD4123	Phase 3
0.7226	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5762	Approved
0.7219	Intermediate Similarity	NPD1375	Discontinued
0.7219	Intermediate Similarity	NPD5763	Approved
0.7212	Intermediate Similarity	NPD2489	Approved
0.7212	Intermediate Similarity	NPD27	Approved
0.7211	Intermediate Similarity	NPD6233	Phase 2
0.7209	Intermediate Similarity	NPD7906	Approved
0.7209	Intermediate Similarity	NPD1242	Phase 1
0.719	Intermediate Similarity	NPD7466	Approved
0.719	Intermediate Similarity	NPD6331	Phase 2
0.719	Intermediate Similarity	NPD4535	Phase 3
0.719	Intermediate Similarity	NPD4628	Phase 3
0.7188	Intermediate Similarity	NPD7819	Suspended
0.7188	Intermediate Similarity	NPD8455	Phase 2
0.7183	Intermediate Similarity	NPD2231	Phase 2
0.7183	Intermediate Similarity	NPD2235	Phase 2
0.7176	Intermediate Similarity	NPD7313	Approved
0.7176	Intermediate Similarity	NPD7311	Approved
0.7176	Intermediate Similarity	NPD7312	Approved
0.7176	Intermediate Similarity	NPD7310	Approved
0.7169	Intermediate Similarity	NPD7473	Discontinued
0.7161	Intermediate Similarity	NPD4357	Discontinued
0.7161	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6799	Approved
0.716	Intermediate Similarity	NPD7240	Approved
0.7154	Intermediate Similarity	NPD940	Approved
0.7154	Intermediate Similarity	NPD846	Approved
0.7154	Intermediate Similarity	NPD291	Approved
0.7152	Intermediate Similarity	NPD2969	Approved
0.7152	Intermediate Similarity	NPD2970	Approved
0.7143	Intermediate Similarity	NPD2560	Approved
0.7143	Intermediate Similarity	NPD2563	Approved
0.7135	Intermediate Similarity	NPD7309	Approved
0.7134	Intermediate Similarity	NPD6959	Discontinued
0.7133	Intermediate Similarity	NPD6583	Phase 3
0.7133	Intermediate Similarity	NPD7097	Phase 1
0.7133	Intermediate Similarity	NPD6582	Phase 2
0.7123	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5536	Phase 2
0.7115	Intermediate Similarity	NPD5401	Approved
0.7115	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD230	Phase 1
0.7114	Intermediate Similarity	NPD4340	Discontinued
0.7097	Intermediate Similarity	NPD7124	Phase 2
0.7093	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6071	Discontinued
0.7091	Intermediate Similarity	NPD3051	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