NPASS Compound

Structure

NPC34456 OpenBabel07101719512D 24 25 0 0 1 0 0 0 0 0999 V2000 0.8660 5.5000 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 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 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 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 9 2 0 0 0 0 5 10 2 0 0 0 0 6 7 1 0 0 0 0 6 9 1 0 0 0 0 7 12 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 10 23 1 0 0 0 0 11 8 1 6 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 18 2 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 1 0 0 0 14 15 1 0 0 0 0 14 20 1 6 0 0 0 15 16 1 0 0 0 0 15 21 1 1 0 0 0 16 23 1 6 0 0 0 16 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.13
Volume:	327.955
LogP:	0.214
LogD:	0.517
LogS:	-1.338
# Rotatable Bonds:	7
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.484
Synthetic Accessibility Score:	3.421
Fsp3:	0.562
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:	-5.612
MDCK Permeability:	8.050427277339622e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.517
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.406
Plasma Protein Binding (PPB):	52.07964324951172%
Volume Distribution (VD):	0.483
Pgp-substrate:	24.980924606323242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.064
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.476
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.308
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	3.061
Half-life (T1/2):	0.928

ADMET: Toxicity

hERG Blockers:	0.147
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.064
AMES Toxicity:	0.206
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.161
Carcinogencity:	0.1
Eye Corrosion:	0.004
Eye Irritation:	0.042
Respiratory Toxicity:	0.014

Download Data

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

Natural Product: NPC34456

Natural Product ID:	NPC34456
*Common Name:**	Methyl Dihydromelilotoside
IUPAC Name:	methyl 3-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]propanoate
Synonyms:	Methyl Dihydromelilotoside
Standard InCHIKey:	UYKGMAOEQCYKNA-YMILTQATSA-N
Standard InCHI:	InChI=1S/C16H22O8/c1-22-12(18)7-6-9-4-2-3-5-10(9)23-16-15(21)14(20)13(19)11(8-17)24-16/h2-5,11,13-17,19-21H,6-8H2,1H3/t11-,13-,14+,15-,16-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccccc2CCC(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1087939
PubChem CID:	46881368
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[19555125]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	twigs	n.a.	n.a.	PMID[22677314]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31458	Cinnamomum cassia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	630000.0	nM	PMID[501168]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	Inhibition	=	22.4	%	PMID[501169]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[501169]

☑ 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 NPC34456 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	275
0.1-0.2	1161
0.2-0.3	3036
0.3-0.4	7276
0.4-0.5	10869
0.5-0.6	5612
0.6-0.7	8896
0.7-0.8	5298
0.8-0.85	236
0.85-0.9	31
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9843	High Similarity	NPC269421
0.9191	High Similarity	NPC164599
0.9098	High Similarity	NPC471029
0.9	High Similarity	NPC469700
0.8992	High Similarity	NPC123704
0.8978	High Similarity	NPC80098
0.8944	High Similarity	NPC107197
0.8931	High Similarity	NPC146540
0.8929	High Similarity	NPC474044
0.8913	High Similarity	NPC31081
0.8913	High Similarity	NPC245219
0.8841	High Similarity	NPC79908
0.8824	High Similarity	NPC294470
0.8794	High Similarity	NPC291153
0.8722	High Similarity	NPC295970
0.8714	High Similarity	NPC242756
0.8714	High Similarity	NPC469367
0.8702	High Similarity	NPC470510
0.8682	High Similarity	NPC226712
0.8681	High Similarity	NPC104172
0.8681	High Similarity	NPC88886
0.8671	High Similarity	NPC218685
0.8652	High Similarity	NPC471028
0.8643	High Similarity	NPC65833
0.8621	High Similarity	NPC213723
0.8613	High Similarity	NPC212729
0.8611	High Similarity	NPC199335
0.8605	High Similarity	NPC469412
0.8605	High Similarity	NPC198734
0.8582	High Similarity	NPC97326
0.8581	High Similarity	NPC127406
0.8562	High Similarity	NPC23253
0.8552	High Similarity	NPC100818
0.8552	High Similarity	NPC182350
0.8551	High Similarity	NPC166180
0.8542	High Similarity	NPC4958
0.8542	High Similarity	NPC302989
0.8542	High Similarity	NPC23084
0.8542	High Similarity	NPC140722
0.8542	High Similarity	NPC92054
0.8527	High Similarity	NPC469708
0.8527	High Similarity	NPC60589
0.8523	High Similarity	NPC43638
0.8511	High Similarity	NPC184053
0.8503	High Similarity	NPC137813
0.8493	Intermediate Similarity	NPC106025
0.8493	Intermediate Similarity	NPC477240
0.8493	Intermediate Similarity	NPC214454
0.8493	Intermediate Similarity	NPC191154
0.8485	Intermediate Similarity	NPC287429
0.8483	Intermediate Similarity	NPC22137
0.8478	Intermediate Similarity	NPC475029
0.8478	Intermediate Similarity	NPC476018
0.8473	Intermediate Similarity	NPC476142
0.8472	Intermediate Similarity	NPC474422
0.8472	Intermediate Similarity	NPC473149
0.8467	Intermediate Similarity	NPC43761
0.8467	Intermediate Similarity	NPC114116
0.8462	Intermediate Similarity	NPC269242
0.8446	Intermediate Similarity	NPC106625
0.8435	Intermediate Similarity	NPC36130
0.8435	Intermediate Similarity	NPC134905
0.8435	Intermediate Similarity	NPC134819
0.8435	Intermediate Similarity	NPC190217
0.8425	Intermediate Similarity	NPC229882
0.8425	Intermediate Similarity	NPC158635
0.8417	Intermediate Similarity	NPC103409
0.8414	Intermediate Similarity	NPC472339
0.8414	Intermediate Similarity	NPC83975
0.8406	Intermediate Similarity	NPC169398
0.8389	Intermediate Similarity	NPC27408
0.8389	Intermediate Similarity	NPC99233
0.8389	Intermediate Similarity	NPC10205
0.8389	Intermediate Similarity	NPC95090
0.8382	Intermediate Similarity	NPC80600
0.8382	Intermediate Similarity	NPC472024
0.8378	Intermediate Similarity	NPC183536
0.8378	Intermediate Similarity	NPC34965
0.8378	Intermediate Similarity	NPC259182
0.8378	Intermediate Similarity	NPC259767
0.8378	Intermediate Similarity	NPC121001
0.8378	Intermediate Similarity	NPC157898
0.8378	Intermediate Similarity	NPC88484
0.837	Intermediate Similarity	NPC40377
0.8367	Intermediate Similarity	NPC475379
0.8367	Intermediate Similarity	NPC93619
0.8367	Intermediate Similarity	NPC131874
0.8358	Intermediate Similarity	NPC233559
0.8356	Intermediate Similarity	NPC111785
0.8356	Intermediate Similarity	NPC287294
0.8355	Intermediate Similarity	NPC85707
0.8355	Intermediate Similarity	NPC259957
0.8355	Intermediate Similarity	NPC48093
0.8355	Intermediate Similarity	NPC216496
0.8355	Intermediate Similarity	NPC159579
0.8355	Intermediate Similarity	NPC224530
0.8355	Intermediate Similarity	NPC101636
0.8355	Intermediate Similarity	NPC129217
0.8345	Intermediate Similarity	NPC185778
0.8344	Intermediate Similarity	NPC279732
0.8333	Intermediate Similarity	NPC85624
0.8333	Intermediate Similarity	NPC295613
0.8333	Intermediate Similarity	NPC473657
0.8333	Intermediate Similarity	NPC226722
0.8333	Intermediate Similarity	NPC471405
0.8333	Intermediate Similarity	NPC45165
0.8333	Intermediate Similarity	NPC206378
0.8322	Intermediate Similarity	NPC299435
0.8322	Intermediate Similarity	NPC83283
0.8322	Intermediate Similarity	NPC29763
0.8322	Intermediate Similarity	NPC191046
0.8322	Intermediate Similarity	NPC78021
0.8322	Intermediate Similarity	NPC87304
0.8322	Intermediate Similarity	NPC143851
0.8322	Intermediate Similarity	NPC210003
0.8322	Intermediate Similarity	NPC194095
0.8322	Intermediate Similarity	NPC185103
0.8322	Intermediate Similarity	NPC475213
0.8322	Intermediate Similarity	NPC152796
0.8322	Intermediate Similarity	NPC268950
0.8322	Intermediate Similarity	NPC327032
0.8322	Intermediate Similarity	NPC211158
0.8322	Intermediate Similarity	NPC260604
0.8322	Intermediate Similarity	NPC108706
0.8322	Intermediate Similarity	NPC39360
0.831	Intermediate Similarity	NPC215512
0.831	Intermediate Similarity	NPC476442
0.8309	Intermediate Similarity	NPC270849
0.8309	Intermediate Similarity	NPC469549
0.8309	Intermediate Similarity	NPC26653
0.8301	Intermediate Similarity	NPC298171
0.8301	Intermediate Similarity	NPC27942
0.8299	Intermediate Similarity	NPC471214
0.8299	Intermediate Similarity	NPC205054
0.8289	Intermediate Similarity	NPC328093
0.8286	Intermediate Similarity	NPC471345
0.8286	Intermediate Similarity	NPC37468
0.8278	Intermediate Similarity	NPC65003
0.8278	Intermediate Similarity	NPC108831
0.8278	Intermediate Similarity	NPC129827
0.8278	Intermediate Similarity	NPC44931
0.8278	Intermediate Similarity	NPC60966
0.8278	Intermediate Similarity	NPC473512
0.8278	Intermediate Similarity	NPC23817
0.8278	Intermediate Similarity	NPC6985
0.8278	Intermediate Similarity	NPC182634
0.8276	Intermediate Similarity	NPC74320
0.8276	Intermediate Similarity	NPC107120
0.8267	Intermediate Similarity	NPC169248
0.8267	Intermediate Similarity	NPC470603
0.8267	Intermediate Similarity	NPC72649
0.8267	Intermediate Similarity	NPC470604
0.8267	Intermediate Similarity	NPC97052
0.8267	Intermediate Similarity	NPC470605
0.8267	Intermediate Similarity	NPC39351
0.8267	Intermediate Similarity	NPC26195
0.8255	Intermediate Similarity	NPC115466
0.8255	Intermediate Similarity	NPC61604
0.8255	Intermediate Similarity	NPC215811
0.8255	Intermediate Similarity	NPC245615
0.8255	Intermediate Similarity	NPC299706
0.8252	Intermediate Similarity	NPC145319
0.8248	Intermediate Similarity	NPC474491
0.8247	Intermediate Similarity	NPC121703
0.8243	Intermediate Similarity	NPC473966
0.8235	Intermediate Similarity	NPC210961
0.8235	Intermediate Similarity	NPC477628
0.8235	Intermediate Similarity	NPC195685
0.8235	Intermediate Similarity	NPC472994
0.8235	Intermediate Similarity	NPC302378
0.8235	Intermediate Similarity	NPC282169
0.8235	Intermediate Similarity	NPC198487
0.8235	Intermediate Similarity	NPC270675
0.8235	Intermediate Similarity	NPC477629
0.8227	Intermediate Similarity	NPC469364
0.8227	Intermediate Similarity	NPC262328
0.8227	Intermediate Similarity	NPC471069
0.8227	Intermediate Similarity	NPC65262
0.8227	Intermediate Similarity	NPC124149
0.8227	Intermediate Similarity	NPC471068
0.8227	Intermediate Similarity	NPC101686
0.8227	Intermediate Similarity	NPC87777
0.8224	Intermediate Similarity	NPC41121
0.8224	Intermediate Similarity	NPC138811
0.8224	Intermediate Similarity	NPC320283
0.8224	Intermediate Similarity	NPC473634
0.8224	Intermediate Similarity	NPC111929
0.8224	Intermediate Similarity	NPC472459
0.8224	Intermediate Similarity	NPC22062
0.8224	Intermediate Similarity	NPC73511
0.8224	Intermediate Similarity	NPC104677
0.8219	Intermediate Similarity	NPC471764
0.8219	Intermediate Similarity	NPC87950
0.8219	Intermediate Similarity	NPC296377
0.8214	Intermediate Similarity	NPC475011
0.8214	Intermediate Similarity	NPC79957
0.8212	Intermediate Similarity	NPC265480
0.8212	Intermediate Similarity	NPC17521
0.8212	Intermediate Similarity	NPC307938
0.8212	Intermediate Similarity	NPC170475

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 NPC34456 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	765
0.2-0.3	1610
0.3-0.4	2609
0.4-0.5	2027
0.5-0.6	1190
0.6-0.7	581
0.7-0.8	133
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8682	High Similarity	NPD1091	Approved
0.8382	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD8455	Phase 2
0.8158	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD7033	Discontinued
0.8116	Intermediate Similarity	NPD6798	Discontinued
0.8058	Intermediate Similarity	NPD6233	Phase 2
0.8	Intermediate Similarity	NPD4628	Phase 3
0.7943	Intermediate Similarity	NPD6355	Discontinued
0.7885	Intermediate Similarity	NPD7199	Phase 2
0.7838	Intermediate Similarity	NPD6799	Approved
0.7836	Intermediate Similarity	NPD1778	Approved
0.7832	Intermediate Similarity	NPD7097	Phase 1
0.7812	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7054	Approved
0.7801	Intermediate Similarity	NPD4062	Phase 3
0.7795	Intermediate Similarity	NPD290	Approved
0.7794	Intermediate Similarity	NPD1608	Approved
0.7793	Intermediate Similarity	NPD6002	Phase 3
0.7793	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6004	Phase 3
0.7793	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD6005	Phase 3
0.7785	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7472	Approved
0.7764	Intermediate Similarity	NPD7074	Phase 3
0.7748	Intermediate Similarity	NPD1653	Approved
0.773	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6797	Phase 2
0.7698	Intermediate Similarity	NPD5647	Approved
0.7692	Intermediate Similarity	NPD7075	Discontinued
0.7687	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1652	Phase 2
0.7682	Intermediate Similarity	NPD5403	Approved
0.7673	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7251	Discontinued
0.7667	Intermediate Similarity	NPD5401	Approved
0.7662	Intermediate Similarity	NPD6801	Discontinued
0.764	Intermediate Similarity	NPD3818	Discontinued
0.7639	Intermediate Similarity	NPD6653	Approved
0.7628	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD2797	Approved
0.7622	Intermediate Similarity	NPD7808	Phase 3
0.761	Intermediate Similarity	NPD3787	Discontinued
0.7606	Intermediate Similarity	NPD3268	Approved
0.76	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6832	Phase 2
0.7574	Intermediate Similarity	NPD17	Approved
0.7569	Intermediate Similarity	NPD1933	Approved
0.7564	Intermediate Similarity	NPD3817	Phase 2
0.7561	Intermediate Similarity	NPD6559	Discontinued
0.7556	Intermediate Similarity	NPD1894	Discontinued
0.7554	Intermediate Similarity	NPD3225	Approved
0.7551	Intermediate Similarity	NPD7266	Discontinued
0.7548	Intermediate Similarity	NPD37	Approved
0.7532	Intermediate Similarity	NPD6599	Discontinued
0.7532	Intermediate Similarity	NPD4380	Phase 2
0.7517	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4967	Phase 2
0.7516	Intermediate Similarity	NPD4966	Approved
0.7516	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD7843	Approved
0.75	Intermediate Similarity	NPD6362	Approved
0.7484	Intermediate Similarity	NPD7411	Suspended
0.747	Intermediate Similarity	NPD8312	Approved
0.747	Intermediate Similarity	NPD8313	Approved
0.7466	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD2684	Approved
0.7452	Intermediate Similarity	NPD5402	Approved
0.7436	Intermediate Similarity	NPD1934	Approved
0.7432	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5763	Approved
0.7432	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5762	Approved
0.7423	Intermediate Similarity	NPD7228	Approved
0.7421	Intermediate Similarity	NPD6234	Discontinued
0.741	Intermediate Similarity	NPD9717	Approved
0.7391	Intermediate Similarity	NPD3496	Discontinued
0.7389	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7819	Suspended
0.7383	Intermediate Similarity	NPD2424	Discontinued
0.7383	Intermediate Similarity	NPD1549	Phase 2
0.7376	Intermediate Similarity	NPD3266	Approved
0.7376	Intermediate Similarity	NPD3267	Approved
0.7372	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6032	Approved
0.7365	Intermediate Similarity	NPD2240	Approved
0.7365	Intermediate Similarity	NPD2239	Approved
0.7349	Intermediate Similarity	NPD7685	Pre-registration
0.7338	Intermediate Similarity	NPD422	Phase 1
0.7338	Intermediate Similarity	NPD1535	Discovery
0.7333	Intermediate Similarity	NPD6674	Discontinued
0.7333	Intermediate Similarity	NPD7157	Approved
0.7329	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD3751	Discontinued
0.7303	Intermediate Similarity	NPD5058	Phase 3
0.7301	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6166	Phase 2
0.7301	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD9545	Approved
0.7286	Intermediate Similarity	NPD1481	Phase 2
0.7285	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5844	Phase 1
0.7267	Intermediate Similarity	NPD4534	Discontinued
0.7267	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1613	Approved
0.726	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4060	Phase 1
0.7254	Intermediate Similarity	NPD1203	Approved
0.7248	Intermediate Similarity	NPD2796	Approved
0.7248	Intermediate Similarity	NPD1551	Phase 2
0.7248	Intermediate Similarity	NPD6099	Approved
0.7248	Intermediate Similarity	NPD6100	Approved
0.7246	Intermediate Similarity	NPD5585	Approved
0.7246	Intermediate Similarity	NPD7240	Approved
0.7244	Intermediate Similarity	NPD7458	Discontinued
0.7241	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6190	Approved
0.7226	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4618	Approved
0.7211	Intermediate Similarity	NPD447	Suspended
0.7211	Intermediate Similarity	NPD4622	Approved
0.7208	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1019	Discontinued
0.719	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD1241	Discontinued
0.7183	Intermediate Similarity	NPD8651	Approved
0.7172	Intermediate Similarity	NPD7095	Approved
0.7171	Intermediate Similarity	NPD4110	Phase 3
0.7171	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2801	Approved
0.7152	Intermediate Similarity	NPD5958	Discontinued
0.7152	Intermediate Similarity	NPD2897	Discontinued
0.7152	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3847	Discontinued
0.7133	Intermediate Similarity	NPD4476	Approved
0.7133	Intermediate Similarity	NPD4477	Approved
0.7125	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1048	Approved
0.7123	Intermediate Similarity	NPD2313	Discontinued
0.7123	Intermediate Similarity	NPD1296	Phase 2
0.7121	Intermediate Similarity	NPD1358	Approved
0.7114	Intermediate Similarity	NPD4538	Approved
0.7114	Intermediate Similarity	NPD5688	Approved
0.7114	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD5689	Approved
0.7114	Intermediate Similarity	NPD4536	Approved
0.7111	Intermediate Similarity	NPD5535	Approved
0.7105	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4908	Phase 1
0.7103	Intermediate Similarity	NPD2614	Approved
0.7095	Intermediate Similarity	NPD4340	Discontinued
0.7095	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD3705	Approved
0.7092	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4972	Discontinued
0.7086	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3882	Suspended
0.708	Intermediate Similarity	NPD6671	Approved
0.7076	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2799	Discontinued
0.7067	Intermediate Similarity	NPD4308	Phase 3
0.7059	Intermediate Similarity	NPD3750	Approved
0.7055	Intermediate Similarity	NPD3027	Phase 3
0.705	Intermediate Similarity	NPD1548	Phase 1
0.7037	Intermediate Similarity	NPD969	Suspended
0.7034	Intermediate Similarity	NPD2861	Phase 2
0.7032	Intermediate Similarity	NPD1511	Approved
0.7027	Intermediate Similarity	NPD1240	Approved
0.7025	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3226	Approved
0.702	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2438	Suspended
0.702	Intermediate Similarity	NPD2935	Discontinued
0.7013	Intermediate Similarity	NPD2354	Approved
0.7013	Intermediate Similarity	NPD3887	Approved
0.7012	Intermediate Similarity	NPD8127	Discontinued
0.7007	Intermediate Similarity	NPD7985	Registered
0.7007	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3685	Discontinued
0.6993	Remote Similarity	NPD4359	Approved
0.6993	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3146	Approved
0.6987	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.698	Remote Similarity	NPD230	Phase 1
0.6974	Remote Similarity	NPD2346	Discontinued
0.6974	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1610	Phase 2
0.697	Remote Similarity	NPD9697	Approved
0.697	Remote Similarity	NPD7229	Phase 3
0.6966	Remote Similarity	NPD2798	Approved
0.6957	Remote Similarity	NPD1465	Phase 2

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