NPASS Compound

Structure

NPC112246 OpenBabel07101718322D 21 23 0 0 1 0 0 0 0 0999 V2000 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 -0.0000 -2.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 -2.5981 -0.5000 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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 7 2 0 0 0 0 4 12 1 0 0 0 0 5 8 1 0 0 0 0 5 11 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 16 2 0 0 0 0 13 19 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 12 1 6 0 0 0 15 21 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.12
Volume:	296.261
LogP:	3.562
LogD:	3.445
LogS:	-4.855
# Rotatable Bonds:	3
TPSA:	47.92
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.938
Synthetic Accessibility Score:	2.586
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.712
MDCK Permeability:	2.9741242542513646e-05
Pgp-inhibitor:	0.182
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	96.45316314697266%
Volume Distribution (VD):	1.046
Pgp-substrate:	3.1654839515686035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.904
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.944
CYP2C19-substrate:	0.741
CYP2C9-inhibitor:	0.833
CYP2C9-substrate:	0.944
CYP2D6-inhibitor:	0.583
CYP2D6-substrate:	0.945
CYP3A4-inhibitor:	0.769
CYP3A4-substrate:	0.729

ADMET: Excretion

Clearance (CL):	13.043
Half-life (T1/2):	0.405

ADMET: Toxicity

hERG Blockers:	0.206
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.829
AMES Toxicity:	0.224
Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.87
Skin Sensitization:	0.8
Carcinogencity:	0.482
Eye Corrosion:	0.043
Eye Irritation:	0.746
Respiratory Toxicity:	0.721

Download Data

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

Natural Product: NPC112246

Natural Product ID:	NPC112246
*Common Name:**	(2S)-4'-Hydroxy-7,3'-Dimethoxyflavan
IUPAC Name:	2-methoxy-4-[(2S)-7-methoxy-3,4-dihydro-2H-chromen-2-yl]phenol
Synonyms:
Standard InCHIKey:	TVAVOTKWLPPGTE-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C17H18O4/c1-19-13-6-3-11-5-8-15(21-16(11)10-13)12-4-7-14(18)17(9-12)20-2/h3-4,6-7,9-10,15,18H,5,8H2,1-2H3/t15-/m0/s1
SMILES:	COc1ccc2CC[C@@H](c3ccc(c(c3)OC)O)Oc2c1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409059
PubChem CID:	14017332
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO12425	Combretum griffithii	Species	Combretaceae	Eukaryota	n.a.	stem	n.a.	PMID[21919533]
NPO12425	Combretum griffithii	Species	Combretaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23795891]
NPO12425	Combretum griffithii	Species	Combretaceae	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	60250.0	nM	PMID[505840]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	88390.0	nM	PMID[505840]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	97880.0	nM	PMID[505840]

☑ 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 NPC112246 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	423
0.1-0.2	1649
0.2-0.3	5042
0.3-0.4	12652
0.4-0.5	4974
0.5-0.6	4031
0.6-0.7	5772
0.7-0.8	5950
0.8-0.85	1127
0.85-0.9	657
0.9-0.95	338
0.95-1	82

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470356
1.0	High Similarity	NPC474206
1.0	High Similarity	NPC121812
1.0	High Similarity	NPC112939
1.0	High Similarity	NPC94750
0.9922	High Similarity	NPC306441
0.9922	High Similarity	NPC16435
0.9922	High Similarity	NPC474639
0.9922	High Similarity	NPC227503
0.9922	High Similarity	NPC230734
0.9846	High Similarity	NPC474282
0.9846	High Similarity	NPC211549
0.9846	High Similarity	NPC107551
0.9846	High Similarity	NPC103976
0.9846	High Similarity	NPC102904
0.9846	High Similarity	NPC176051
0.9846	High Similarity	NPC326797
0.9845	High Similarity	NPC151224
0.9845	High Similarity	NPC260898
0.9845	High Similarity	NPC234333
0.9845	High Similarity	NPC61946
0.9845	High Similarity	NPC47398
0.9844	High Similarity	NPC11060
0.9769	High Similarity	NPC270456
0.9769	High Similarity	NPC265433
0.9769	High Similarity	NPC248727
0.9769	High Similarity	NPC269091
0.9769	High Similarity	NPC302701
0.9769	High Similarity	NPC162659
0.9767	High Similarity	NPC317380
0.9766	High Similarity	NPC127624
0.9766	High Similarity	NPC202762
0.9766	High Similarity	NPC86655
0.9697	High Similarity	NPC184797
0.9697	High Similarity	NPC309124
0.9695	High Similarity	NPC276490
0.9692	High Similarity	NPC473413
0.9692	High Similarity	NPC164787
0.969	High Similarity	NPC263064
0.969	High Similarity	NPC168059
0.969	High Similarity	NPC229442
0.969	High Similarity	NPC475840
0.9624	High Similarity	NPC471389
0.9621	High Similarity	NPC127218
0.9621	High Similarity	NPC25966
0.9621	High Similarity	NPC70682
0.9621	High Similarity	NPC473739
0.9621	High Similarity	NPC236306
0.9621	High Similarity	NPC260741
0.9621	High Similarity	NPC232164
0.9621	High Similarity	NPC245207
0.9621	High Similarity	NPC319647
0.9618	High Similarity	NPC472336
0.9618	High Similarity	NPC234952
0.9618	High Similarity	NPC470802
0.9618	High Similarity	NPC472334
0.9615	High Similarity	NPC170694
0.9612	High Similarity	NPC78770
0.9612	High Similarity	NPC261619
0.9612	High Similarity	NPC253105
0.9612	High Similarity	NPC201587
0.9612	High Similarity	NPC185604
0.9612	High Similarity	NPC15658
0.9612	High Similarity	NPC61477
0.9612	High Similarity	NPC219876
0.9612	High Similarity	NPC126029
0.9552	High Similarity	NPC107161
0.9549	High Similarity	NPC22317
0.9542	High Similarity	NPC195022
0.9542	High Similarity	NPC472337
0.9535	High Similarity	NPC268266
0.9535	High Similarity	NPC268342
0.9535	High Similarity	NPC220825
0.9535	High Similarity	NPC472597
0.9535	High Similarity	NPC42760
0.9481	High Similarity	NPC81638
0.9478	High Similarity	NPC247291
0.9478	High Similarity	NPC35216
0.9474	High Similarity	NPC32630
0.9474	High Similarity	NPC471388
0.947	High Similarity	NPC173660
0.9466	High Similarity	NPC478085
0.9466	High Similarity	NPC106215
0.9462	High Similarity	NPC7903
0.9462	High Similarity	NPC35932
0.9462	High Similarity	NPC470752
0.9462	High Similarity	NPC160991
0.9462	High Similarity	NPC16208
0.9462	High Similarity	NPC184447
0.9457	High Similarity	NPC91291
0.9457	High Similarity	NPC472338
0.9453	High Similarity	NPC46274
0.9453	High Similarity	NPC31707
0.9453	High Similarity	NPC226331
0.9412	High Similarity	NPC50250
0.9412	High Similarity	NPC93323
0.9412	High Similarity	NPC473108
0.9412	High Similarity	NPC280092
0.9412	High Similarity	NPC45257
0.9412	High Similarity	NPC12641
0.9407	High Similarity	NPC2613
0.9407	High Similarity	NPC204347
0.9407	High Similarity	NPC59841
0.9407	High Similarity	NPC475891
0.9403	High Similarity	NPC160283
0.9403	High Similarity	NPC254759
0.9403	High Similarity	NPC259519
0.9403	High Similarity	NPC27495
0.9394	High Similarity	NPC134968
0.9385	High Similarity	NPC309787
0.938	High Similarity	NPC86030
0.938	High Similarity	NPC5851
0.938	High Similarity	NPC190629
0.938	High Similarity	NPC212015
0.938	High Similarity	NPC218856
0.938	High Similarity	NPC273295
0.938	High Similarity	NPC222004
0.938	High Similarity	NPC476968
0.938	High Similarity	NPC170844
0.938	High Similarity	NPC285339
0.938	High Similarity	NPC210623
0.938	High Similarity	NPC3439
0.938	High Similarity	NPC226788
0.938	High Similarity	NPC202582
0.938	High Similarity	NPC470258
0.9375	High Similarity	NPC5447
0.9375	High Similarity	NPC250432
0.9375	High Similarity	NPC124452
0.9375	High Similarity	NPC82679
0.9375	High Similarity	NPC236791
0.9375	High Similarity	NPC246620
0.9375	High Similarity	NPC282000
0.9375	High Similarity	NPC159968
0.9375	High Similarity	NPC74817
0.9375	High Similarity	NPC169474
0.9375	High Similarity	NPC210355
0.9375	High Similarity	NPC324112
0.9375	High Similarity	NPC293054
0.9343	High Similarity	NPC475096
0.9338	High Similarity	NPC85264
0.9338	High Similarity	NPC47633
0.9338	High Similarity	NPC102044
0.9333	High Similarity	NPC263261
0.9333	High Similarity	NPC87725
0.9333	High Similarity	NPC178054
0.9333	High Similarity	NPC265075
0.9328	High Similarity	NPC292882
0.9328	High Similarity	NPC22517
0.9318	High Similarity	NPC310854
0.9308	High Similarity	NPC214860
0.9308	High Similarity	NPC51840
0.9308	High Similarity	NPC299221
0.9308	High Similarity	NPC234488
0.9308	High Similarity	NPC311680
0.9302	High Similarity	NPC470213
0.9302	High Similarity	NPC252307
0.9302	High Similarity	NPC206615
0.9302	High Similarity	NPC245826
0.9302	High Similarity	NPC474178
0.9302	High Similarity	NPC98631
0.9302	High Similarity	NPC186843
0.9302	High Similarity	NPC87224
0.9302	High Similarity	NPC222572
0.9302	High Similarity	NPC72529
0.9297	High Similarity	NPC223136
0.9297	High Similarity	NPC103823
0.9297	High Similarity	NPC18924
0.9297	High Similarity	NPC44748
0.9297	High Similarity	NPC28730
0.9297	High Similarity	NPC214406
0.9297	High Similarity	NPC78974
0.9275	High Similarity	NPC233980
0.9275	High Similarity	NPC99515
0.9275	High Similarity	NPC125755
0.9275	High Similarity	NPC190714
0.927	High Similarity	NPC171932
0.927	High Similarity	NPC63879
0.927	High Similarity	NPC28440
0.9265	High Similarity	NPC475084
0.9265	High Similarity	NPC189115
0.9259	High Similarity	NPC266197
0.9259	High Similarity	NPC262189
0.9259	High Similarity	NPC291101
0.9254	High Similarity	NPC474390
0.9248	High Similarity	NPC256262
0.9242	High Similarity	NPC36661
0.9242	High Similarity	NPC158331
0.9237	High Similarity	NPC469613
0.9237	High Similarity	NPC470095
0.9237	High Similarity	NPC469625
0.9237	High Similarity	NPC474017
0.9237	High Similarity	NPC470096
0.9237	High Similarity	NPC30043
0.9237	High Similarity	NPC103799
0.9231	High Similarity	NPC10225
0.9231	High Similarity	NPC469963
0.9231	High Similarity	NPC45824
0.9231	High Similarity	NPC469951
0.9231	High Similarity	NPC58164
0.9225	High Similarity	NPC242032

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 NPC112246 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	892
0.2-0.3	1908
0.3-0.4	2695
0.4-0.5	1552
0.5-0.6	876
0.6-0.7	658
0.7-0.8	175
0.8-0.85	12
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9612	High Similarity	NPD1612	Clinical (unspecified phase)
0.9612	High Similarity	NPD1613	Approved
0.9453	High Similarity	NPD1529	Clinical (unspecified phase)
0.938	High Similarity	NPD3027	Phase 3
0.9375	High Similarity	NPD1530	Clinical (unspecified phase)
0.8722	High Similarity	NPD4908	Phase 1
0.8699	High Similarity	NPD1934	Approved
0.8615	High Similarity	NPD1610	Phase 2
0.8593	High Similarity	NPD4907	Clinical (unspecified phase)
0.8514	High Similarity	NPD2393	Clinical (unspecified phase)
0.845	Intermediate Similarity	NPD1548	Phase 1
0.837	Intermediate Similarity	NPD2861	Phase 2
0.8299	Intermediate Similarity	NPD1653	Approved
0.8278	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD2801	Approved
0.8258	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6166	Phase 2
0.8248	Intermediate Similarity	NPD4625	Phase 3
0.8235	Intermediate Similarity	NPD3018	Phase 2
0.8209	Intermediate Similarity	NPD4749	Approved
0.8074	Intermediate Similarity	NPD2982	Phase 2
0.8074	Intermediate Similarity	NPD2983	Phase 2
0.8058	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD7074	Phase 3
0.8047	Intermediate Similarity	NPD228	Approved
0.8039	Intermediate Similarity	NPD3882	Suspended
0.8027	Intermediate Similarity	NPD1511	Approved
0.8	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2981	Phase 2
0.7987	Intermediate Similarity	NPD7054	Approved
0.7937	Intermediate Similarity	NPD7472	Approved
0.7935	Intermediate Similarity	NPD6234	Discontinued
0.7926	Intermediate Similarity	NPD1091	Approved
0.7925	Intermediate Similarity	NPD3818	Discontinued
0.7923	Intermediate Similarity	NPD5283	Phase 1
0.7919	Intermediate Similarity	NPD1512	Approved
0.7877	Intermediate Similarity	NPD6674	Discontinued
0.7857	Intermediate Similarity	NPD3817	Phase 2
0.7817	Intermediate Similarity	NPD1558	Phase 1
0.7817	Intermediate Similarity	NPD4060	Phase 1
0.781	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD6671	Approved
0.7801	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7212	Phase 2
0.7785	Intermediate Similarity	NPD7213	Phase 3
0.7778	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD4536	Approved
0.7778	Intermediate Similarity	NPD4538	Approved
0.7764	Intermediate Similarity	NPD5844	Phase 1
0.7755	Intermediate Similarity	NPD1652	Phase 2
0.774	Intermediate Similarity	NPD7266	Discontinued
0.774	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7447	Phase 1
0.773	Intermediate Similarity	NPD7251	Discontinued
0.7727	Intermediate Similarity	NPD37	Approved
0.7722	Intermediate Similarity	NPD7199	Phase 2
0.7712	Intermediate Similarity	NPD4380	Phase 2
0.7712	Intermediate Similarity	NPD4675	Approved
0.7712	Intermediate Similarity	NPD4678	Approved
0.7702	Intermediate Similarity	NPD7228	Approved
0.7692	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4966	Approved
0.7692	Intermediate Similarity	NPD4965	Approved
0.7692	Intermediate Similarity	NPD4967	Phase 2
0.7692	Intermediate Similarity	NPD3620	Phase 2
0.7687	Intermediate Similarity	NPD1549	Phase 2
0.7683	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7808	Phase 3
0.7677	Intermediate Similarity	NPD1465	Phase 2
0.7674	Intermediate Similarity	NPD2684	Approved
0.7669	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD422	Phase 1
0.7658	Intermediate Similarity	NPD5494	Approved
0.7651	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7075	Discontinued
0.7643	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD5124	Phase 1
0.7635	Intermediate Similarity	NPD5177	Phase 3
0.7626	Intermediate Similarity	NPD8651	Approved
0.7625	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3540	Phase 1
0.7616	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD3021	Approved
0.7615	Intermediate Similarity	NPD3022	Approved
0.7603	Intermediate Similarity	NPD5588	Approved
0.7603	Intermediate Similarity	NPD5960	Phase 3
0.7597	Intermediate Similarity	NPD290	Approved
0.7576	Intermediate Similarity	NPD7843	Approved
0.7564	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6798	Discontinued
0.7551	Intermediate Similarity	NPD3539	Phase 1
0.7551	Intermediate Similarity	NPD6100	Approved
0.7551	Intermediate Similarity	NPD6099	Approved
0.7537	Intermediate Similarity	NPD7157	Approved
0.7536	Intermediate Similarity	NPD3705	Approved
0.7532	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6584	Phase 3
0.7518	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8053	Approved
0.7485	Intermediate Similarity	NPD8054	Approved
0.7483	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5058	Phase 3
0.747	Intermediate Similarity	NPD7549	Discontinued
0.7453	Intermediate Similarity	NPD6232	Discontinued
0.7451	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2796	Approved
0.7429	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4005	Discontinued
0.7417	Intermediate Similarity	NPD2677	Approved
0.741	Intermediate Similarity	NPD6559	Discontinued
0.7405	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3060	Approved
0.7397	Intermediate Similarity	NPD6355	Discontinued
0.7391	Intermediate Similarity	NPD5846	Approved
0.7391	Intermediate Similarity	NPD6516	Phase 2
0.7386	Intermediate Similarity	NPD4123	Phase 3
0.7385	Intermediate Similarity	NPD968	Approved
0.7379	Intermediate Similarity	NPD6233	Phase 2
0.7365	Intermediate Similarity	NPD1510	Phase 2
0.7361	Intermediate Similarity	NPD7095	Approved
0.7351	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3750	Approved
0.7351	Intermediate Similarity	NPD3892	Phase 2
0.7351	Intermediate Similarity	NPD6331	Phase 2
0.7344	Intermediate Similarity	NPD940	Approved
0.7344	Intermediate Similarity	NPD846	Approved
0.7342	Intermediate Similarity	NPD7819	Suspended
0.7333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2424	Discontinued
0.732	Intermediate Similarity	NPD6799	Approved
0.732	Intermediate Similarity	NPD1774	Approved
0.732	Intermediate Similarity	NPD4357	Discontinued
0.732	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1357	Approved
0.7317	Intermediate Similarity	NPD7473	Discontinued
0.7305	Intermediate Similarity	NPD6583	Phase 3
0.7305	Intermediate Similarity	NPD6582	Phase 2
0.7303	Intermediate Similarity	NPD6190	Approved
0.7299	Intermediate Similarity	NPD5536	Phase 2
0.7296	Intermediate Similarity	NPD5402	Approved
0.7292	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4237	Approved
0.7285	Intermediate Similarity	NPD4162	Approved
0.7285	Intermediate Similarity	NPD4236	Phase 3
0.7284	Intermediate Similarity	NPD6959	Discontinued
0.7279	Intermediate Similarity	NPD230	Phase 1
0.7279	Intermediate Similarity	NPD5735	Approved
0.7278	Intermediate Similarity	NPD6801	Discontinued
0.7273	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5763	Approved
0.7267	Intermediate Similarity	NPD5762	Approved
0.7267	Intermediate Similarity	NPD1375	Discontinued
0.7266	Intermediate Similarity	NPD1242	Phase 1
0.7256	Intermediate Similarity	NPD27	Approved
0.7256	Intermediate Similarity	NPD2489	Approved
0.7255	Intermediate Similarity	NPD7124	Phase 2
0.7251	Intermediate Similarity	NPD7906	Approved
0.7248	Intermediate Similarity	NPD7033	Discontinued
0.7239	Intermediate Similarity	NPD3787	Discontinued
0.7237	Intermediate Similarity	NPD4535	Phase 3
0.7237	Intermediate Similarity	NPD4628	Phase 3
0.7237	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7466	Approved
0.7237	Intermediate Similarity	NPD4110	Phase 3
0.7226	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7313	Approved
0.7219	Intermediate Similarity	NPD7310	Approved
0.7219	Intermediate Similarity	NPD7311	Approved
0.7219	Intermediate Similarity	NPD7312	Approved
0.7219	Intermediate Similarity	NPD4577	Approved
0.7219	Intermediate Similarity	NPD4578	Approved
0.7218	Intermediate Similarity	NPD4750	Phase 3
0.7215	Intermediate Similarity	NPD7411	Suspended
0.7214	Intermediate Similarity	NPD3496	Discontinued
0.7211	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1240	Approved
0.7211	Intermediate Similarity	NPD2238	Phase 2
0.7209	Intermediate Similarity	NPD291	Approved
0.7202	Intermediate Similarity	NPD7240	Approved
0.72	Intermediate Similarity	NPD6032	Approved
0.7195	Intermediate Similarity	NPD2970	Approved
0.7195	Intermediate Similarity	NPD2969	Approved
0.7193	Intermediate Similarity	NPD4663	Approved
0.719	Intermediate Similarity	NPD2219	Phase 1
0.7188	Intermediate Similarity	NPD2560	Approved
0.7188	Intermediate Similarity	NPD2563	Approved
0.7185	Intermediate Similarity	NPD5535	Approved
0.7181	Intermediate Similarity	NPD7097	Phase 1
0.7179	Intermediate Similarity	NPD5403	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