NPASS Compound

Structure

NPC83218 OpenBabel07101719512D 30 32 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 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 0.8660 3.5000 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 3 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 -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 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 -1.7321 0.0000 0.0000 C 0 0 2 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 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 -0.8660 -2.5000 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 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 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 8 1 0 0 0 0 5 12 2 0 0 0 0 6 9 2 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 9 13 1 0 0 0 0 10 17 1 0 0 0 0 11 22 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 28 1 0 0 0 0 16 11 1 6 0 0 0 16 18 1 0 0 0 0 16 29 1 0 0 0 0 17 25 2 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 1 0 0 0 19 20 1 0 0 0 0 19 27 1 6 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 28 1 6 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.17
Volume:	412.033
LogP:	1.129
LogD:	1.57
LogS:	-1.917
# Rotatable Bonds:	7
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.316
Synthetic Accessibility Score:	4.045
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.919
MDCK Permeability:	2.9172422728152014e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.433
Human Intestinal Absorption (HIA):	0.951
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.308
Plasma Protein Binding (PPB):	85.09210205078125%
Volume Distribution (VD):	0.751
Pgp-substrate:	9.338380813598633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.134
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.6
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.097

ADMET: Excretion

Clearance (CL):	6.588
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.178
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.187
Rat Oral Acute Toxicity:	0.298
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.932
Carcinogencity:	0.111
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.061

Download Data

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

Natural Product: NPC83218

Natural Product ID:	NPC83218
*Common Name:**	Grandidentatin
IUPAC Name:	[(2R,3R,4S,5S,6R)-4,5-dihydroxy-2-(2-hydroxycyclohexyl)oxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:	Grandidentatin
Standard InCHIKey:	ZTMPDTJBTNGZJH-CBUJGKTRSA-N
Standard InCHI:	InChI=1S/C21H28O9/c22-11-16-18(26)19(27)20(21(29-16)28-15-4-2-1-3-14(15)24)30-17(25)10-7-12-5-8-13(23)9-6-12/h5-10,14-16,18-24,26-27H,1-4,11H2/b10-7+/t14?,15?,16-,18-,19+,20-,21-/m1/s1
SMILES:	C1CCC(C(C1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)OC(=O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517169
PubChem CID:	44559108
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

*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
NPO14695	Populus davidiana	Species	Salicaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[16989539]
NPO14695	Populus davidiana	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14695	Populus davidiana	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14695	Populus davidiana	Species	Salicaceae	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		Activity	=	1.27	n.a.	PMID[495248]

☑ 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 NPC83218 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	286
0.1-0.2	1286
0.2-0.3	3432
0.3-0.4	8467
0.4-0.5	9989
0.5-0.6	8277
0.6-0.7	8899
0.7-0.8	1711
0.8-0.85	204
0.85-0.9	107
0.9-0.95	22
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC126991
0.9916	High Similarity	NPC471157
0.9746	High Similarity	NPC52097
0.9669	High Similarity	NPC288416
0.9661	High Similarity	NPC11724
0.959	High Similarity	NPC225307
0.9587	High Similarity	NPC252114
0.9576	High Similarity	NPC476872
0.9508	High Similarity	NPC106677
0.936	High Similarity	NPC138777
0.936	High Similarity	NPC478255
0.936	High Similarity	NPC235294
0.936	High Similarity	NPC246869
0.936	High Similarity	NPC46137
0.936	High Similarity	NPC225384
0.9355	High Similarity	NPC477293
0.9355	High Similarity	NPC477294
0.9355	High Similarity	NPC253595
0.9355	High Similarity	NPC229784
0.935	High Similarity	NPC471881
0.935	High Similarity	NPC45224
0.935	High Similarity	NPC35288
0.935	High Similarity	NPC173150
0.935	High Similarity	NPC471882
0.935	High Similarity	NPC156692
0.9291	High Similarity	NPC886
0.9291	High Similarity	NPC34293
0.9291	High Similarity	NPC287597
0.9286	High Similarity	NPC473285
0.9274	High Similarity	NPC232880
0.9219	High Similarity	NPC476870
0.9213	High Similarity	NPC28637
0.9206	High Similarity	NPC254819
0.9206	High Similarity	NPC219677
0.9194	High Similarity	NPC476873
0.9134	High Similarity	NPC473924
0.9113	High Similarity	NPC61181
0.9077	High Similarity	NPC260425
0.9077	High Similarity	NPC78363
0.907	High Similarity	NPC263829
0.9062	High Similarity	NPC254398
0.9055	High Similarity	NPC281798
0.904	High Similarity	NPC103533
0.9008	High Similarity	NPC81515
0.9008	High Similarity	NPC197316
0.9008	High Similarity	NPC321184
0.9008	High Similarity	NPC171134
0.9008	High Similarity	NPC205195
0.9008	High Similarity	NPC472350
0.9008	High Similarity	NPC89105
0.9008	High Similarity	NPC328273
0.9008	High Similarity	NPC476383
0.9008	High Similarity	NPC64141
0.9008	High Similarity	NPC321638
0.9008	High Similarity	NPC68092
0.9	High Similarity	NPC471345
0.9	High Similarity	NPC166180
0.8992	High Similarity	NPC471883
0.8983	High Similarity	NPC313193
0.8931	High Similarity	NPC476376
0.8898	High Similarity	NPC295970
0.8872	High Similarity	NPC476377
0.8872	High Similarity	NPC47471
0.8872	High Similarity	NPC186406
0.8872	High Similarity	NPC134405
0.8872	High Similarity	NPC476385
0.8855	High Similarity	NPC470572
0.8855	High Similarity	NPC472132
0.8855	High Similarity	NPC157554
0.8846	High Similarity	NPC169398
0.8833	High Similarity	NPC175771
0.8806	High Similarity	NPC265648
0.8806	High Similarity	NPC140502
0.8806	High Similarity	NPC157816
0.8806	High Similarity	NPC222433
0.8797	High Similarity	NPC473799
0.8797	High Similarity	NPC475530
0.8797	High Similarity	NPC202700
0.878	High Similarity	NPC201402
0.878	High Similarity	NPC469703
0.878	High Similarity	NPC160854
0.878	High Similarity	NPC469704
0.8741	High Similarity	NPC298257
0.8741	High Similarity	NPC247032
0.8741	High Similarity	NPC119537
0.8741	High Similarity	NPC476384
0.8741	High Similarity	NPC175214
0.8741	High Similarity	NPC105005
0.8741	High Similarity	NPC76406
0.8741	High Similarity	NPC476380
0.8741	High Similarity	NPC112
0.8741	High Similarity	NPC476378
0.8741	High Similarity	NPC476375
0.8741	High Similarity	NPC476381
0.8741	High Similarity	NPC269141
0.8741	High Similarity	NPC40305
0.8741	High Similarity	NPC476397
0.8741	High Similarity	NPC478239
0.8741	High Similarity	NPC264632
0.8741	High Similarity	NPC205864
0.8741	High Similarity	NPC96795
0.8722	High Similarity	NPC100389
0.8722	High Similarity	NPC220936
0.8722	High Similarity	NPC49597
0.8722	High Similarity	NPC31745
0.8722	High Similarity	NPC226005
0.8722	High Similarity	NPC220942
0.8712	High Similarity	NPC186418
0.8712	High Similarity	NPC37468
0.871	High Similarity	NPC469686
0.8678	High Similarity	NPC148055
0.8676	High Similarity	NPC232228
0.8676	High Similarity	NPC110063
0.8676	High Similarity	NPC296954
0.8676	High Similarity	NPC292443
0.8676	High Similarity	NPC476867
0.8676	High Similarity	NPC64195
0.8676	High Similarity	NPC300894
0.8676	High Similarity	NPC141455
0.8676	High Similarity	NPC196063
0.8672	High Similarity	NPC146540
0.8667	High Similarity	NPC157338
0.8667	High Similarity	NPC145319
0.8647	High Similarity	NPC101686
0.8647	High Similarity	NPC469364
0.8647	High Similarity	NPC65262
0.864	High Similarity	NPC471067
0.8626	High Similarity	NPC114116
0.8613	High Similarity	NPC34587
0.8613	High Similarity	NPC100998
0.8613	High Similarity	NPC252292
0.8613	High Similarity	NPC476382
0.8613	High Similarity	NPC34927
0.8613	High Similarity	NPC287615
0.8613	High Similarity	NPC216819
0.8613	High Similarity	NPC476864
0.8613	High Similarity	NPC262182
0.8613	High Similarity	NPC476869
0.8613	High Similarity	NPC83743
0.8613	High Similarity	NPC476866
0.8613	High Similarity	NPC476868
0.8603	High Similarity	NPC204644
0.8603	High Similarity	NPC478250
0.8593	High Similarity	NPC46644
0.8571	High Similarity	NPC470907
0.8571	High Similarity	NPC178449
0.8571	High Similarity	NPC232454
0.856	High Similarity	NPC55608
0.8551	High Similarity	NPC229505
0.8551	High Similarity	NPC476865
0.8551	High Similarity	NPC199928
0.8548	High Similarity	NPC282409
0.8548	High Similarity	NPC469702
0.8529	High Similarity	NPC296643
0.8507	High Similarity	NPC124149
0.8496	Intermediate Similarity	NPC185778
0.8496	Intermediate Similarity	NPC123988
0.8489	Intermediate Similarity	NPC232992
0.848	Intermediate Similarity	NPC469548
0.848	Intermediate Similarity	NPC229600
0.848	Intermediate Similarity	NPC476445
0.848	Intermediate Similarity	NPC476448
0.8475	Intermediate Similarity	NPC184633
0.8467	Intermediate Similarity	NPC293154
0.8462	Intermediate Similarity	NPC469549
0.845	Intermediate Similarity	NPC264900
0.845	Intermediate Similarity	NPC108659
0.845	Intermediate Similarity	NPC231607
0.845	Intermediate Similarity	NPC79715
0.8433	Intermediate Similarity	NPC103409
0.843	Intermediate Similarity	NPC474641
0.8429	Intermediate Similarity	NPC80732
0.8429	Intermediate Similarity	NPC261122
0.8429	Intermediate Similarity	NPC3460
0.8429	Intermediate Similarity	NPC192763
0.8429	Intermediate Similarity	NPC215095
0.8429	Intermediate Similarity	NPC210611
0.8429	Intermediate Similarity	NPC28651
0.8429	Intermediate Similarity	NPC478237
0.8429	Intermediate Similarity	NPC201148
0.8429	Intermediate Similarity	NPC199311
0.8429	Intermediate Similarity	NPC300262
0.8417	Intermediate Similarity	NPC470825
0.8417	Intermediate Similarity	NPC291153
0.8417	Intermediate Similarity	NPC320734
0.8413	Intermediate Similarity	NPC266045
0.8409	Intermediate Similarity	NPC254275
0.8406	Intermediate Similarity	NPC251062
0.8406	Intermediate Similarity	NPC184464
0.8406	Intermediate Similarity	NPC77922
0.8406	Intermediate Similarity	NPC63304
0.8406	Intermediate Similarity	NPC473281
0.8406	Intermediate Similarity	NPC296659
0.8406	Intermediate Similarity	NPC297342
0.8406	Intermediate Similarity	NPC202391
0.8397	Intermediate Similarity	NPC470122
0.8397	Intermediate Similarity	NPC469705
0.8397	Intermediate Similarity	NPC17968
0.8394	Intermediate Similarity	NPC65833
0.8394	Intermediate Similarity	NPC148080

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 NPC83218 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	753
0.2-0.3	1601
0.3-0.4	3051
0.4-0.5	1948
0.5-0.6	1210
0.6-0.7	334
0.7-0.8	17
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9008	High Similarity	NPD7266	Discontinued
0.8112	Intermediate Similarity	NPD1653	Approved
0.7984	Intermediate Similarity	NPD1091	Approved
0.7943	Intermediate Similarity	NPD6190	Approved
0.7571	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD969	Suspended
0.75	Intermediate Similarity	NPD1358	Approved
0.7405	Intermediate Similarity	NPD9545	Approved
0.7368	Intermediate Similarity	NPD8455	Phase 2
0.7329	Intermediate Similarity	NPD7685	Pre-registration
0.731	Intermediate Similarity	NPD1652	Phase 2
0.7305	Intermediate Similarity	NPD4340	Discontinued
0.728	Intermediate Similarity	NPD3134	Approved
0.7266	Intermediate Similarity	NPD3027	Phase 3
0.726	Intermediate Similarity	NPD4628	Phase 3
0.7234	Intermediate Similarity	NPD1613	Approved
0.7234	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7097	Phase 1
0.7188	Intermediate Similarity	NPD3818	Discontinued
0.7183	Intermediate Similarity	NPD230	Phase 1
0.7178	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4380	Phase 2
0.7164	Intermediate Similarity	NPD5125	Phase 3
0.7164	Intermediate Similarity	NPD5126	Approved
0.7163	Intermediate Similarity	NPD6233	Phase 2
0.7161	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7054	Approved
0.7117	Intermediate Similarity	NPD6559	Discontinued
0.7099	Intermediate Similarity	NPD7472	Approved
0.7099	Intermediate Similarity	NPD7074	Phase 3
0.7092	Intermediate Similarity	NPD3764	Approved
0.709	Intermediate Similarity	NPD1357	Approved
0.7081	Intermediate Similarity	NPD7228	Approved
0.7078	Intermediate Similarity	NPD37	Approved
0.707	Intermediate Similarity	NPD6234	Discontinued
0.7063	Intermediate Similarity	NPD5124	Phase 1
0.7063	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD422	Phase 1
0.7055	Intermediate Similarity	NPD6797	Phase 2
0.7051	Intermediate Similarity	NPD4965	Approved
0.7051	Intermediate Similarity	NPD4966	Approved
0.7051	Intermediate Similarity	NPD4967	Phase 2
0.7047	Intermediate Similarity	NPD5058	Phase 3
0.7037	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7251	Discontinued
0.7006	Intermediate Similarity	NPD7075	Discontinued
0.6974	Remote Similarity	NPD5403	Approved
0.6972	Remote Similarity	NPD6798	Discontinued
0.697	Remote Similarity	NPD7808	Phase 3
0.6959	Remote Similarity	NPD6674	Discontinued
0.695	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7843	Approved
0.6934	Remote Similarity	NPD3705	Approved
0.6928	Remote Similarity	NPD8312	Approved
0.6928	Remote Similarity	NPD8313	Approved
0.6913	Remote Similarity	NPD8166	Discontinued
0.6906	Remote Similarity	NPD3225	Approved
0.6899	Remote Similarity	NPD2684	Approved
0.6889	Remote Similarity	NPD1548	Phase 1
0.6885	Remote Similarity	NPD2934	Approved
0.6885	Remote Similarity	NPD2933	Approved
0.6879	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2861	Phase 2
0.6875	Remote Similarity	NPD4060	Phase 1
0.6863	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6801	Discontinued
0.6853	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4536	Approved
0.6849	Remote Similarity	NPD4538	Approved
0.6846	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5401	Approved
0.6831	Remote Similarity	NPD4908	Phase 1
0.6829	Remote Similarity	NPD2859	Approved
0.6829	Remote Similarity	NPD2860	Approved
0.6828	Remote Similarity	NPD1933	Approved
0.6822	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD290	Approved
0.6818	Remote Similarity	NPD5535	Approved
0.6815	Remote Similarity	NPD5536	Phase 2
0.6815	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1610	Phase 2
0.6806	Remote Similarity	NPD4062	Phase 3
0.6803	Remote Similarity	NPD5588	Approved
0.6803	Remote Similarity	NPD5960	Phase 3
0.6803	Remote Similarity	NPD7033	Discontinued
0.68	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7157	Approved
0.6779	Remote Similarity	NPD1549	Phase 2
0.6776	Remote Similarity	NPD6799	Approved
0.6772	Remote Similarity	NPD5402	Approved
0.677	Remote Similarity	NPD7199	Phase 2
0.6759	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD1934	Approved
0.675	Remote Similarity	NPD689	Discontinued
0.6747	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1242	Phase 1
0.6744	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD968	Approved
0.6741	Remote Similarity	NPD9493	Approved
0.6741	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3496	Discontinued
0.6738	Remote Similarity	NPD3094	Phase 2
0.6736	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3536	Discontinued
0.6718	Remote Similarity	NPD3021	Approved
0.6718	Remote Similarity	NPD3022	Approved
0.6712	Remote Similarity	NPD6355	Discontinued
0.6711	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7240	Approved
0.6691	Remote Similarity	NPD1535	Discovery
0.669	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3750	Approved
0.6688	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD2424	Discontinued
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD5846	Approved
0.6667	Remote Similarity	NPD3020	Approved
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD3455	Phase 2
0.6667	Remote Similarity	NPD6516	Phase 2
0.6667	Remote Similarity	NPD6653	Approved
0.6646	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6166	Phase 2
0.6644	Remote Similarity	NPD1551	Phase 2
0.6644	Remote Similarity	NPD2935	Discontinued
0.6643	Remote Similarity	NPD1481	Phase 2
0.6643	Remote Similarity	NPD9269	Phase 2
0.6643	Remote Similarity	NPD5736	Approved
0.6642	Remote Similarity	NPD1894	Discontinued
0.6627	Remote Similarity	NPD5844	Phase 1
0.6623	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1203	Approved
0.662	Remote Similarity	NPD2797	Approved
0.6619	Remote Similarity	NPD3847	Discontinued
0.6617	Remote Similarity	NPD228	Approved
0.66	Remote Similarity	NPD5763	Approved
0.66	Remote Similarity	NPD5762	Approved
0.6596	Remote Similarity	NPD2983	Phase 2
0.6596	Remote Similarity	NPD2982	Phase 2
0.6585	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1510	Phase 2
0.6573	Remote Similarity	NPD5647	Approved
0.6571	Remote Similarity	NPD3092	Approved
0.6564	Remote Similarity	NPD8127	Discontinued
0.6562	Remote Similarity	NPD940	Approved
0.6562	Remote Similarity	NPD846	Approved
0.6555	Remote Similarity	NPD111	Approved
0.6552	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD8651	Approved
0.6547	Remote Similarity	NPD4626	Approved
0.6538	Remote Similarity	NPD5048	Discontinued
0.6538	Remote Similarity	NPD9697	Approved
0.6532	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4140	Approved
0.6528	Remote Similarity	NPD9494	Approved
0.6525	Remote Similarity	NPD2981	Phase 2
0.6524	Remote Similarity	NPD3787	Discontinued
0.6519	Remote Similarity	NPD6599	Discontinued
0.6516	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD3268	Approved
0.65	Remote Similarity	NPD2978	Approved
0.65	Remote Similarity	NPD2977	Approved
0.65	Remote Similarity	NPD1465	Phase 2
0.65	Remote Similarity	NPD7819	Suspended
0.65	Remote Similarity	NPD2801	Approved
0.6497	Remote Similarity	NPD3686	Approved
0.6497	Remote Similarity	NPD3687	Approved
0.6494	Remote Similarity	NPD7440	Discontinued
0.6483	Remote Similarity	NPD6832	Phase 2
0.6479	Remote Similarity	NPD4659	Approved
0.6479	Remote Similarity	NPD3685	Discontinued
0.6478	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD9268	Approved
0.6475	Remote Similarity	NPD5691	Approved
0.6471	Remote Similarity	NPD2629	Approved
0.6471	Remote Similarity	NPD3400	Discontinued
0.6471	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4108	Discontinued
0.6466	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6663	Approved
0.6452	Remote Similarity	NPD1511	Approved
0.6452	Remote Similarity	NPD4357	Discontinued
0.6446	Remote Similarity	NPD1282	Approved
0.6443	Remote Similarity	NPD2492	Phase 1
0.6438	Remote Similarity	NPD3179	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