NPASS Compound

Structure

NPC213416 OpenBabel07101719512D 26 30 0 0 1 0 0 0 0 0999 V2000 -6.8690 1.0000 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 0.0000 1.0000 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 -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 0 0 0 0 0 0 0 0 0 0 -5.8690 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 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 -4.3301 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 -5.2812 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 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 -3.4641 -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 -4.3301 0.5000 0.0000 C 0 0 0 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 -1.7321 -0.0000 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 -5.5902 2.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 19 1 0 0 0 0 6 8 1 0 0 0 0 6 20 1 0 0 0 0 7 1 1 1 0 0 0 7 12 1 0 0 0 0 7 26 1 0 0 0 0 8 20 1 6 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 21 1 6 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 23 2 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 18 2 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.14
Volume:	351.253
LogP:	3.608
LogD:	2.001
LogS:	-3.566
# Rotatable Bonds:	0
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.539
Synthetic Accessibility Score:	4.861
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.109
MDCK Permeability:	9.52863319980679e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.258
Human Intestinal Absorption (HIA):	0.125
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	93.82219696044922%
Volume Distribution (VD):	0.931
Pgp-substrate:	9.277665138244629%

ADMET: Metabolism

CYP1A2-inhibitor:	0.268
CYP1A2-substrate:	0.906
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.542
CYP2C9-inhibitor:	0.293
CYP2C9-substrate:	0.343
CYP2D6-inhibitor:	0.145
CYP2D6-substrate:	0.183
CYP3A4-inhibitor:	0.19
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	10.326
Half-life (T1/2):	0.226

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.513
Rat Oral Acute Toxicity:	0.205
Maximum Recommended Daily Dose:	0.272
Skin Sensitization:	0.864
Carcinogencity:	0.443
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.441

Download Data

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

Natural Product: NPC213416

Natural Product ID:	NPC213416
*Common Name:**	QPWSRTWYKXMXRY-PHWXQYABSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QPWSRTWYKXMXRY-PHWXQYABSA-N
Standard InCHI:	InChI=1S/C20H22O6/c1-7-12(21)10-13(22)9-11(15(24)17(10)26-7)19(2)5-4-8-6-20(8,3)18(19)16(25)14(9)23/h7-8,12,21-22,24-25H,4-6H2,1-3H3/t7-,8-,12-,19+,20+/m0/s1
SMILES:	C[C@H]1[C@@H](c2c(c3c(c(c2O1)O)[C@@]1(C)CC[C@H]2C[C@@]2(C)C1=C(C3=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1287850
PubChem CID:	52949735
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO24239	Teucrium polium	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[21084196]
NPO24239	Teucrium polium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24239	Teucrium polium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24239	Teucrium polium	Species	Lamiaceae	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	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	84000.0	nM	PMID[493227]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	50.0	%	PMID[493227]

☑ 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 NPC213416 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	450
0.1-0.2	1921
0.2-0.3	3868
0.3-0.4	9277
0.4-0.5	9524
0.5-0.6	4860
0.6-0.7	6268
0.7-0.8	5766
0.8-0.85	681
0.85-0.9	50
0.9-0.95	18
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC232936
0.981	High Similarity	NPC146584
0.981	High Similarity	NPC21016
0.9747	High Similarity	NPC208120
0.9747	High Similarity	NPC173587
0.9686	High Similarity	NPC102372
0.9379	High Similarity	NPC475055
0.9259	High Similarity	NPC29055
0.9181	High Similarity	NPC240808
0.9119	High Similarity	NPC273248
0.9057	High Similarity	NPC161778
0.9006	High Similarity	NPC25850
0.9006	High Similarity	NPC246153
0.9006	High Similarity	NPC276815
0.9006	High Similarity	NPC228209
0.8951	High Similarity	NPC283301
0.8895	High Similarity	NPC240508
0.8895	High Similarity	NPC8927
0.8869	High Similarity	NPC315306
0.8869	High Similarity	NPC313717
0.8855	High Similarity	NPC326520
0.8855	High Similarity	NPC473286
0.883	High Similarity	NPC23553
0.883	High Similarity	NPC77179
0.8802	High Similarity	NPC170245
0.8788	High Similarity	NPC65746
0.875	High Similarity	NPC45760
0.8743	High Similarity	NPC25361
0.8727	High Similarity	NPC161947
0.8727	High Similarity	NPC155302
0.8721	High Similarity	NPC221820
0.869	High Similarity	NPC472452
0.8683	High Similarity	NPC475985
0.8683	High Similarity	NPC472278
0.8683	High Similarity	NPC270837
0.8683	High Similarity	NPC476822
0.8683	High Similarity	NPC472281
0.8683	High Similarity	NPC18100
0.8683	High Similarity	NPC205265
0.8683	High Similarity	NPC329669
0.8683	High Similarity	NPC220313
0.8683	High Similarity	NPC236132
0.8683	High Similarity	NPC473313
0.8683	High Similarity	NPC197168
0.8683	High Similarity	NPC7483
0.8678	High Similarity	NPC182693
0.8675	High Similarity	NPC87431
0.8675	High Similarity	NPC187354
0.8663	High Similarity	NPC478050
0.8647	High Similarity	NPC472276
0.8639	High Similarity	NPC117854
0.8639	High Similarity	NPC126204
0.8639	High Similarity	NPC470456
0.8639	High Similarity	NPC477154
0.8639	High Similarity	NPC6588
0.8631	High Similarity	NPC314653
0.8631	High Similarity	NPC316262
0.8631	High Similarity	NPC472277
0.8631	High Similarity	NPC470457
0.8631	High Similarity	NPC475888
0.8623	High Similarity	NPC215612
0.8623	High Similarity	NPC81679
0.8623	High Similarity	NPC294965
0.8623	High Similarity	NPC211107
0.8623	High Similarity	NPC470694
0.8614	High Similarity	NPC14353
0.8614	High Similarity	NPC56085
0.8614	High Similarity	NPC228785
0.8613	High Similarity	NPC246877
0.8606	High Similarity	NPC179732
0.8603	High Similarity	NPC314020
0.8589	High Similarity	NPC218628
0.8588	High Similarity	NPC475805
0.8588	High Similarity	NPC165456
0.858	High Similarity	NPC470462
0.8571	High Similarity	NPC474240
0.8571	High Similarity	NPC41301
0.8571	High Similarity	NPC470459
0.8571	High Similarity	NPC273959
0.8563	High Similarity	NPC32694
0.8563	High Similarity	NPC117985
0.8563	High Similarity	NPC474186
0.8563	High Similarity	NPC278052
0.8563	High Similarity	NPC61010
0.8563	High Similarity	NPC40491
0.8563	High Similarity	NPC476273
0.8563	High Similarity	NPC66288
0.8554	High Similarity	NPC250214
0.8554	High Similarity	NPC329091
0.8554	High Similarity	NPC95936
0.8554	High Similarity	NPC85121
0.8554	High Similarity	NPC100123
0.8547	High Similarity	NPC471969
0.8547	High Similarity	NPC470942
0.8538	High Similarity	NPC102277
0.8538	High Similarity	NPC101107
0.8538	High Similarity	NPC279209
0.8529	High Similarity	NPC474024
0.8529	High Similarity	NPC158761
0.8503	High Similarity	NPC246478
0.8503	High Similarity	NPC476283
0.8503	High Similarity	NPC282009
0.8503	High Similarity	NPC475886
0.8503	High Similarity	NPC320359
0.8503	High Similarity	NPC470810
0.8503	High Similarity	NPC287328
0.8503	High Similarity	NPC263449
0.8503	High Similarity	NPC36217
0.8503	High Similarity	NPC119224
0.8503	High Similarity	NPC474287
0.8503	High Similarity	NPC470326
0.8503	High Similarity	NPC313368
0.8503	High Similarity	NPC235018
0.8503	High Similarity	NPC45146
0.8503	High Similarity	NPC80375
0.8497	Intermediate Similarity	NPC245975
0.8494	Intermediate Similarity	NPC302258
0.8494	Intermediate Similarity	NPC217677
0.8494	Intermediate Similarity	NPC241904
0.8494	Intermediate Similarity	NPC469584
0.8494	Intermediate Similarity	NPC300727
0.8494	Intermediate Similarity	NPC223787
0.8494	Intermediate Similarity	NPC165977
0.8488	Intermediate Similarity	NPC121333
0.8485	Intermediate Similarity	NPC477687
0.8485	Intermediate Similarity	NPC477671
0.848	Intermediate Similarity	NPC476637
0.848	Intermediate Similarity	NPC242395
0.848	Intermediate Similarity	NPC326877
0.848	Intermediate Similarity	NPC152477
0.848	Intermediate Similarity	NPC288813
0.8471	Intermediate Similarity	NPC43319
0.8471	Intermediate Similarity	NPC128293
0.8471	Intermediate Similarity	NPC235610
0.8471	Intermediate Similarity	NPC37870
0.8466	Intermediate Similarity	NPC50269
0.8462	Intermediate Similarity	NPC152659
0.8462	Intermediate Similarity	NPC248638
0.8462	Intermediate Similarity	NPC236521
0.8462	Intermediate Similarity	NPC124038
0.8462	Intermediate Similarity	NPC476295
0.8457	Intermediate Similarity	NPC244903
0.8452	Intermediate Similarity	NPC474239
0.8452	Intermediate Similarity	NPC278427
0.8452	Intermediate Similarity	NPC474351
0.8452	Intermediate Similarity	NPC308992
0.8452	Intermediate Similarity	NPC472275
0.8452	Intermediate Similarity	NPC471499
0.8452	Intermediate Similarity	NPC475883
0.8452	Intermediate Similarity	NPC266314
0.8452	Intermediate Similarity	NPC474187
0.8448	Intermediate Similarity	NPC98943
0.8448	Intermediate Similarity	NPC8127
0.8448	Intermediate Similarity	NPC49667
0.8443	Intermediate Similarity	NPC22192
0.8443	Intermediate Similarity	NPC235448
0.8443	Intermediate Similarity	NPC476242
0.8443	Intermediate Similarity	NPC477410
0.8434	Intermediate Similarity	NPC470762
0.8434	Intermediate Similarity	NPC477674
0.8434	Intermediate Similarity	NPC164427
0.8434	Intermediate Similarity	NPC274730
0.8434	Intermediate Similarity	NPC474167
0.8434	Intermediate Similarity	NPC477675
0.8434	Intermediate Similarity	NPC142339
0.843	Intermediate Similarity	NPC477670
0.843	Intermediate Similarity	NPC17219
0.8427	Intermediate Similarity	NPC174486
0.8421	Intermediate Similarity	NPC225419
0.8421	Intermediate Similarity	NPC473094
0.8421	Intermediate Similarity	NPC150131
0.8421	Intermediate Similarity	NPC247973
0.8421	Intermediate Similarity	NPC218226
0.8415	Intermediate Similarity	NPC477672
0.8415	Intermediate Similarity	NPC477673
0.8412	Intermediate Similarity	NPC239752
0.8412	Intermediate Similarity	NPC472450
0.8412	Intermediate Similarity	NPC275780
0.8412	Intermediate Similarity	NPC108433
0.8412	Intermediate Similarity	NPC224280
0.8412	Intermediate Similarity	NPC62261
0.8402	Intermediate Similarity	NPC220912
0.8402	Intermediate Similarity	NPC25152
0.8402	Intermediate Similarity	NPC472635
0.8402	Intermediate Similarity	NPC472402
0.8402	Intermediate Similarity	NPC201800
0.8402	Intermediate Similarity	NPC48860
0.8395	Intermediate Similarity	NPC251188
0.8393	Intermediate Similarity	NPC472962
0.8393	Intermediate Similarity	NPC321399
0.8393	Intermediate Similarity	NPC84571
0.8393	Intermediate Similarity	NPC472961
0.8393	Intermediate Similarity	NPC472624
0.8391	Intermediate Similarity	NPC227906
0.8391	Intermediate Similarity	NPC287243
0.8383	Intermediate Similarity	NPC262286
0.8383	Intermediate Similarity	NPC470402
0.8383	Intermediate Similarity	NPC474836
0.8383	Intermediate Similarity	NPC472911
0.8383	Intermediate Similarity	NPC474208

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 NPC213416 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	1158
0.2-0.3	2322
0.3-0.4	2610
0.4-0.5	1638
0.5-0.6	691
0.6-0.7	261
0.7-0.8	88
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8214	Intermediate Similarity	NPD3882	Suspended
0.8204	Intermediate Similarity	NPD2801	Approved
0.8204	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5494	Approved
0.8144	Intermediate Similarity	NPD1934	Approved
0.8092	Intermediate Similarity	NPD6166	Phase 2
0.8092	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD2800	Approved
0.8049	Intermediate Similarity	NPD2533	Approved
0.8049	Intermediate Similarity	NPD2532	Approved
0.8049	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD3818	Discontinued
0.7955	Intermediate Similarity	NPD5844	Phase 1
0.7943	Intermediate Similarity	NPD7473	Discontinued
0.7877	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD6232	Discontinued
0.7816	Intermediate Similarity	NPD6959	Discontinued
0.7784	Intermediate Similarity	NPD1512	Approved
0.7733	Intermediate Similarity	NPD3817	Phase 2
0.7725	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7074	Phase 3
0.7702	Intermediate Similarity	NPD6651	Approved
0.7667	Intermediate Similarity	NPD6797	Phase 2
0.7665	Intermediate Similarity	NPD1511	Approved
0.7654	Intermediate Similarity	NPD7054	Approved
0.7644	Intermediate Similarity	NPD7075	Discontinued
0.7624	Intermediate Similarity	NPD7251	Discontinued
0.7616	Intermediate Similarity	NPD6801	Discontinued
0.7614	Intermediate Similarity	NPD1247	Approved
0.7611	Intermediate Similarity	NPD7472	Approved
0.7602	Intermediate Similarity	NPD6599	Discontinued
0.7602	Intermediate Similarity	NPD4380	Phase 2
0.7586	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7808	Phase 3
0.7572	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD6559	Discontinued
0.7527	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7473	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD5710	Approved
0.7472	Intermediate Similarity	NPD5711	Approved
0.7471	Intermediate Similarity	NPD1465	Phase 2
0.7471	Intermediate Similarity	NPD7819	Suspended
0.7459	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5402	Approved
0.7414	Intermediate Similarity	NPD37	Approved
0.7386	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD4965	Approved
0.7386	Intermediate Similarity	NPD4967	Phase 2
0.7366	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4111	Phase 1
0.7333	Intermediate Similarity	NPD3926	Phase 2
0.7308	Intermediate Similarity	NPD7228	Approved
0.7308	Intermediate Similarity	NPD3751	Discontinued
0.7305	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD919	Approved
0.7262	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1549	Phase 2
0.7251	Intermediate Similarity	NPD6799	Approved
0.7246	Intermediate Similarity	NPD6099	Approved
0.7246	Intermediate Similarity	NPD6100	Approved
0.7238	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8150	Discontinued
0.7222	Intermediate Similarity	NPD7199	Phase 2
0.7209	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD3787	Discontinued
0.7179	Intermediate Similarity	NPD6782	Approved
0.7179	Intermediate Similarity	NPD6779	Approved
0.7179	Intermediate Similarity	NPD6777	Approved
0.7179	Intermediate Similarity	NPD6776	Approved
0.7179	Intermediate Similarity	NPD6778	Approved
0.7179	Intermediate Similarity	NPD6781	Approved
0.7179	Intermediate Similarity	NPD6780	Approved
0.7176	Intermediate Similarity	NPD4628	Phase 3
0.7171	Intermediate Similarity	NPD4665	Approved
0.7143	Intermediate Similarity	NPD2796	Approved
0.7121	Intermediate Similarity	NPD4583	Approved
0.7121	Intermediate Similarity	NPD4582	Approved
0.711	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1510	Phase 2
0.7076	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD8312	Approved
0.7074	Intermediate Similarity	NPD8313	Approved
0.7071	Intermediate Similarity	NPD7435	Discontinued
0.7071	Intermediate Similarity	NPD4004	Approved
0.7071	Intermediate Similarity	NPD4002	Approved
0.7066	Intermediate Similarity	NPD1607	Approved
0.7062	Intermediate Similarity	NPD7411	Suspended
0.7056	Intermediate Similarity	NPD3749	Approved
0.7045	Intermediate Similarity	NPD3226	Approved
0.7029	Intermediate Similarity	NPD5403	Approved
0.7021	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7907	Approved
0.7018	Intermediate Similarity	NPD6674	Discontinued
0.7011	Intermediate Similarity	NPD2403	Approved
0.701	Intermediate Similarity	NPD6534	Approved
0.701	Intermediate Similarity	NPD6535	Approved
0.7005	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2346	Discontinued
0.6985	Remote Similarity	NPD7696	Phase 3
0.6985	Remote Similarity	NPD7698	Approved
0.6985	Remote Similarity	NPD7697	Approved
0.6977	Remote Similarity	NPD3750	Approved
0.697	Remote Similarity	NPD2494	Approved
0.697	Remote Similarity	NPD2493	Approved
0.6954	Remote Similarity	NPD7390	Discontinued
0.695	Remote Similarity	NPD7870	Phase 2
0.695	Remote Similarity	NPD7871	Phase 2
0.6946	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD943	Approved
0.6946	Remote Similarity	NPD1613	Approved
0.6946	Remote Similarity	NPD1240	Approved
0.6941	Remote Similarity	NPD2935	Discontinued
0.6932	Remote Similarity	NPD920	Approved
0.6931	Remote Similarity	NPD7701	Phase 2
0.6919	Remote Similarity	NPD4580	Approved
0.6919	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5401	Approved
0.6914	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7801	Approved
0.6906	Remote Similarity	NPD7768	Phase 2
0.6905	Remote Similarity	NPD230	Phase 1
0.6904	Remote Similarity	NPD7700	Phase 2
0.6904	Remote Similarity	NPD7699	Phase 2
0.6897	Remote Similarity	NPD8151	Discontinued
0.6889	Remote Similarity	NPD5761	Phase 2
0.6889	Remote Similarity	NPD5760	Phase 2
0.6884	Remote Similarity	NPD3452	Approved
0.6884	Remote Similarity	NPD3450	Approved
0.6879	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7240	Approved
0.6867	Remote Similarity	NPD3027	Phase 3
0.6863	Remote Similarity	NPD7874	Approved
0.6863	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD2490	Approved
0.6856	Remote Similarity	NPD2488	Approved
0.685	Remote Similarity	NPD3057	Approved
0.685	Remote Similarity	NPD2491	Approved
0.6848	Remote Similarity	NPD8127	Discontinued
0.6839	Remote Similarity	NPD6190	Approved
0.6836	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7783	Phase 2
0.6829	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7985	Registered
0.6811	Remote Similarity	NPD7229	Phase 3
0.6798	Remote Similarity	NPD1653	Approved
0.6792	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7685	Pre-registration
0.6777	Remote Similarity	NPD8366	Approved
0.6768	Remote Similarity	NPD2974	Approved
0.6768	Remote Similarity	NPD2973	Approved
0.6768	Remote Similarity	NPD2975	Approved
0.6766	Remote Similarity	NPD2972	Approved
0.6766	Remote Similarity	NPD3448	Approved
0.6766	Remote Similarity	NPD6823	Phase 2
0.6766	Remote Similarity	NPD3533	Approved
0.676	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7048	Phase 3
0.6747	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3620	Phase 2
0.6744	Remote Similarity	NPD1551	Phase 2
0.6724	Remote Similarity	NPD1243	Approved
0.6724	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD642	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7286	Phase 2
0.6707	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD447	Suspended
0.6705	Remote Similarity	NPD2344	Approved
0.6686	Remote Similarity	NPD3748	Approved
0.6686	Remote Similarity	NPD2799	Discontinued
0.6685	Remote Similarity	NPD6273	Approved
0.6684	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4363	Phase 3
0.6667	Remote Similarity	NPD6696	Suspended
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4360	Phase 2
0.6651	Remote Similarity	NPD8491	Approved
0.6649	Remote Similarity	NPD5953	Discontinued
0.6647	Remote Similarity	NPD4060	Phase 1
0.6633	Remote Similarity	NPD4361	Phase 2
0.6633	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8320	Phase 1
0.6618	Remote Similarity	NPD8319	Approved
0.6617	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD6214	Clinical (unspecified phase)

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