NPASS Compound

Structure

NPC124149 OpenBabel07101718302D 29 31 0 0 1 0 0 0 0 0999 V2000 2.5981 -2.5000 0.0000 C 0 0 0 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 -2.5981 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 -5.1962 2.0000 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 -6.0622 1.5000 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 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 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 -0.0000 2.0000 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 1 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 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 2.5981 -1.5000 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 -0.0000 -0.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 3 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 6 1 0 0 0 0 4 13 2 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 17 2 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 11 27 1 0 0 0 0 12 22 2 0 0 0 0 12 28 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 6 0 0 0 19 20 1 0 0 0 0 19 25 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 6 0 0 0 21 27 1 0 0 0 0 21 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.13
Volume:	395.333
LogP:	2.432
LogD:	2.276
LogS:	-2.78
# Rotatable Bonds:	6
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.439
Synthetic Accessibility Score:	3.731
Fsp3:	0.286
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:	1.1530589290487114e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.963
Human Intestinal Absorption (HIA):	0.387
20% Bioavailability (F20%):	0.822
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	96.79436492919922%
Volume Distribution (VD):	0.617
Pgp-substrate:	2.536816120147705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.488
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.66
CYP2D6-inhibitor:	0.25
CYP2D6-substrate:	0.741
CYP3A4-inhibitor:	0.719
CYP3A4-substrate:	0.09

ADMET: Excretion

Clearance (CL):	4.962
Half-life (T1/2):	0.867

ADMET: Toxicity

hERG Blockers:	0.46
Human Hepatotoxicity (H-HT):	0.263
Drug-inuced Liver Injury (DILI):	0.679
AMES Toxicity:	0.485
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.303
Skin Sensitization:	0.953
Carcinogencity:	0.42
Eye Corrosion:	0.003
Eye Irritation:	0.146
Respiratory Toxicity:	0.11

Download Data

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

Natural Product: NPC124149

Natural Product ID:	NPC124149
*Common Name:**	(E)-Resveratrol 3-(4' '-Acetyl)-O-Beta-D-Xylopyranoside
IUPAC Name:	[(3R,4R,5R,6S)-4,5-dihydroxy-6-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]oxan-3-yl] acetate
Synonyms:
Standard InCHIKey:	UMVYQMNABVJEMU-UOHLNVAWSA-N
Standard InCHI:	InChI=1S/C21H22O8/c1-12(22)28-18-11-27-21(20(26)19(18)25)29-17-9-14(8-16(24)10-17)3-2-13-4-6-15(23)7-5-13/h2-10,18-21,23-26H,11H2,1H3/b3-2+/t18-,19+,20-,21+/m1/s1
SMILES:	CC(=O)O[C@@H]1CO[C@H]([C@@H]([C@H]1O)O)Oc1cc(/C=C/c2ccc(cc2)O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512671
PubChem CID:	11292556
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes [CHEMONTID:0000142] Stilbene 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
NPO32936	calligonum leucocladum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217293]

☑ 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.		Ratio	=	0.2	n.a.	PMID[555948]

☑ 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 NPC124149 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	299
0.1-0.2	1437
0.2-0.3	4036
0.3-0.4	10032
0.4-0.5	8464
0.5-0.6	4864
0.6-0.7	7614
0.7-0.8	5022
0.8-0.85	743
0.85-0.9	131
0.9-0.95	48
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9692	High Similarity	NPC115022
0.9692	High Similarity	NPC294166
0.9615	High Similarity	NPC85799
0.9615	High Similarity	NPC303422
0.9615	High Similarity	NPC26080
0.9615	High Similarity	NPC165686
0.9545	High Similarity	NPC238243
0.9538	High Similarity	NPC121376
0.9474	High Similarity	NPC197723
0.9474	High Similarity	NPC165482
0.9474	High Similarity	NPC40664
0.9474	High Similarity	NPC3293
0.9474	High Similarity	NPC138350
0.947	High Similarity	NPC130496
0.947	High Similarity	NPC188555
0.9398	High Similarity	NPC185778
0.9385	High Similarity	NPC218003
0.9333	High Similarity	NPC212770
0.9333	High Similarity	NPC98777
0.9328	High Similarity	NPC242028
0.9328	High Similarity	NPC203230
0.9286	High Similarity	NPC478237
0.9259	High Similarity	NPC59324
0.9259	High Similarity	NPC65530
0.922	High Similarity	NPC106138
0.9197	High Similarity	NPC210192
0.9197	High Similarity	NPC257095
0.9197	High Similarity	NPC89686
0.9197	High Similarity	NPC273932
0.913	High Similarity	NPC475084
0.913	High Similarity	NPC157816
0.913	High Similarity	NPC469559
0.913	High Similarity	NPC189115
0.913	High Similarity	NPC145319
0.9104	High Similarity	NPC49074
0.9098	High Similarity	NPC475067
0.9077	High Similarity	NPC12308
0.9071	High Similarity	NPC226722
0.9065	High Similarity	NPC478239
0.9065	High Similarity	NPC473044
0.9058	High Similarity	NPC186406
0.9058	High Similarity	NPC469661
0.9044	High Similarity	NPC164857
0.9044	High Similarity	NPC166180
0.903	High Similarity	NPC162093
0.9028	High Similarity	NPC169404
0.9028	High Similarity	NPC53587
0.9028	High Similarity	NPC176186
0.9014	High Similarity	NPC93924
0.9007	High Similarity	NPC107120
0.9007	High Similarity	NPC74320
0.9007	High Similarity	NPC199928
0.9	High Similarity	NPC25292
0.9	High Similarity	NPC473045
0.9	High Similarity	NPC292443
0.8978	High Similarity	NPC262328
0.8978	High Similarity	NPC87777
0.8978	High Similarity	NPC134260
0.8971	High Similarity	NPC470236
0.8966	High Similarity	NPC150442
0.8963	High Similarity	NPC132895
0.8951	High Similarity	NPC283839
0.8951	High Similarity	NPC90896
0.8947	High Similarity	NPC295970
0.8936	High Similarity	NPC475096
0.8929	High Similarity	NPC252169
0.8913	High Similarity	NPC100389
0.8905	High Similarity	NPC37468
0.8905	High Similarity	NPC471719
0.8897	High Similarity	NPC48863
0.8897	High Similarity	NPC251981
0.8897	High Similarity	NPC13745
0.8889	High Similarity	NPC299144
0.8881	High Similarity	NPC262606
0.8873	High Similarity	NPC476865
0.8873	High Similarity	NPC125755
0.8873	High Similarity	NPC99515
0.8873	High Similarity	NPC190714
0.8865	High Similarity	NPC476867
0.8865	High Similarity	NPC138227
0.8865	High Similarity	NPC76176
0.8865	High Similarity	NPC232228
0.8865	High Similarity	NPC168579
0.8865	High Similarity	NPC469313
0.8865	High Similarity	NPC297342
0.8857	High Similarity	NPC140502
0.8849	High Similarity	NPC210478
0.8849	High Similarity	NPC202700
0.8841	High Similarity	NPC470413
0.8841	High Similarity	NPC138738
0.8828	High Similarity	NPC213197
0.8824	High Similarity	NPC69513
0.8824	High Similarity	NPC215833
0.8815	High Similarity	NPC469698
0.8815	High Similarity	NPC473412
0.8811	High Similarity	NPC227902
0.8811	High Similarity	NPC39657
0.8811	High Similarity	NPC41844
0.8811	High Similarity	NPC473480
0.8811	High Similarity	NPC15538
0.8806	High Similarity	NPC248355
0.8803	High Similarity	NPC161700
0.8803	High Similarity	NPC277867
0.8803	High Similarity	NPC476864
0.8803	High Similarity	NPC476869
0.8803	High Similarity	NPC476866
0.8803	High Similarity	NPC476868
0.8794	High Similarity	NPC37793
0.8768	High Similarity	NPC172818
0.8768	High Similarity	NPC25695
0.8768	High Similarity	NPC186418
0.8768	High Similarity	NPC103409
0.8768	High Similarity	NPC157554
0.8767	High Similarity	NPC302610
0.8767	High Similarity	NPC476352
0.8767	High Similarity	NPC472612
0.8767	High Similarity	NPC472611
0.8767	High Similarity	NPC215060
0.8767	High Similarity	NPC289967
0.8759	High Similarity	NPC107478
0.8759	High Similarity	NPC309744
0.8759	High Similarity	NPC170694
0.8759	High Similarity	NPC187194
0.875	High Similarity	NPC96294
0.875	High Similarity	NPC470270
0.875	High Similarity	NPC175976
0.8732	High Similarity	NPC110063
0.8731	High Similarity	NPC302378
0.8723	High Similarity	NPC49542
0.8723	High Similarity	NPC472353
0.8723	High Similarity	NPC128337
0.8723	High Similarity	NPC84207
0.8723	High Similarity	NPC472714
0.8723	High Similarity	NPC5253
0.8723	High Similarity	NPC139976
0.8723	High Similarity	NPC5262
0.8723	High Similarity	NPC230718
0.8705	High Similarity	NPC195196
0.869	High Similarity	NPC212670
0.869	High Similarity	NPC55158
0.869	High Similarity	NPC313334
0.869	High Similarity	NPC206264
0.869	High Similarity	NPC51328
0.869	High Similarity	NPC286235
0.8681	High Similarity	NPC52740
0.8671	High Similarity	NPC252292
0.8671	High Similarity	NPC34587
0.8671	High Similarity	NPC100998
0.8671	High Similarity	NPC34927
0.8671	High Similarity	NPC138915
0.8671	High Similarity	NPC476382
0.8671	High Similarity	NPC85624
0.8671	High Similarity	NPC216819
0.8671	High Similarity	NPC287615
0.8671	High Similarity	NPC83743
0.8671	High Similarity	NPC262182
0.8667	High Similarity	NPC307110
0.8667	High Similarity	NPC160780
0.8667	High Similarity	NPC166040
0.8667	High Similarity	NPC289811
0.8652	High Similarity	NPC215512
0.8652	High Similarity	NPC108674
0.8652	High Similarity	NPC476442
0.8649	High Similarity	NPC260604
0.8649	High Similarity	NPC299435
0.8643	High Similarity	NPC226005
0.8633	High Similarity	NPC52277
0.8633	High Similarity	NPC104167
0.8633	High Similarity	NPC199459
0.8633	High Similarity	NPC177035
0.863	High Similarity	NPC100818
0.863	High Similarity	NPC114740
0.8623	High Similarity	NPC476411
0.8621	High Similarity	NPC187398
0.8621	High Similarity	NPC130449
0.8621	High Similarity	NPC248132
0.8621	High Similarity	NPC476348
0.8621	High Similarity	NPC169510
0.8621	High Similarity	NPC280945
0.8613	High Similarity	NPC35932
0.8613	High Similarity	NPC184447
0.8613	High Similarity	NPC16208
0.8613	High Similarity	NPC160991
0.8613	High Similarity	NPC7903
0.8611	High Similarity	NPC212890
0.8609	High Similarity	NPC239966
0.8609	High Similarity	NPC203020
0.8603	High Similarity	NPC80600
0.8603	High Similarity	NPC472024
0.8601	High Similarity	NPC473046
0.8601	High Similarity	NPC225445
0.8601	High Similarity	NPC472712
0.8601	High Similarity	NPC472713
0.8601	High Similarity	NPC187774
0.8601	High Similarity	NPC118385
0.86	High Similarity	NPC1913
0.8593	High Similarity	NPC40377
0.8592	High Similarity	NPC193722
0.8592	High Similarity	NPC278469
0.8582	High Similarity	NPC106944

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 NPC124149 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	820
0.2-0.3	1803
0.3-0.4	2808
0.4-0.5	1799
0.5-0.6	987
0.6-0.7	573
0.7-0.8	111
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.869	High Similarity	NPD1653	Approved
0.838	Intermediate Similarity	NPD7266	Discontinued
0.8346	Intermediate Similarity	NPD1091	Approved
0.8345	Intermediate Similarity	NPD1613	Approved
0.8345	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD3027	Phase 3
0.8117	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7054	Approved
0.7986	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD37	Approved
0.7963	Intermediate Similarity	NPD6559	Discontinued
0.795	Intermediate Similarity	NPD7472	Approved
0.795	Intermediate Similarity	NPD7074	Phase 3
0.7949	Intermediate Similarity	NPD6234	Discontinued
0.7937	Intermediate Similarity	NPD7228	Approved
0.7935	Intermediate Similarity	NPD4965	Approved
0.7935	Intermediate Similarity	NPD4967	Phase 2
0.7935	Intermediate Similarity	NPD4966	Approved
0.7929	Intermediate Similarity	NPD4908	Phase 1
0.7914	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6797	Phase 2
0.7891	Intermediate Similarity	NPD1652	Phase 2
0.7853	Intermediate Similarity	NPD7251	Discontinued
0.7848	Intermediate Similarity	NPD7199	Phase 2
0.7826	Intermediate Similarity	NPD3818	Discontinued
0.7821	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1610	Phase 2
0.7806	Intermediate Similarity	NPD8455	Phase 2
0.7805	Intermediate Similarity	NPD7808	Phase 3
0.7778	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1548	Phase 1
0.7708	Intermediate Similarity	NPD4060	Phase 1
0.7681	Intermediate Similarity	NPD422	Phase 1
0.7658	Intermediate Similarity	NPD7075	Discontinued
0.7655	Intermediate Similarity	NPD5124	Phase 1
0.7655	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD6233	Phase 2
0.7628	Intermediate Similarity	NPD1934	Approved
0.7616	Intermediate Similarity	NPD5058	Phase 3
0.7606	Intermediate Similarity	NPD2861	Phase 2
0.758	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD2983	Phase 2
0.7571	Intermediate Similarity	NPD2982	Phase 2
0.7551	Intermediate Similarity	NPD7097	Phase 1
0.7533	Intermediate Similarity	NPD6674	Discontinued
0.7532	Intermediate Similarity	NPD5402	Approved
0.7532	Intermediate Similarity	NPD3817	Phase 2
0.753	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD2981	Phase 2
0.75	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD7095	Approved
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7468	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1357	Approved
0.7451	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6798	Discontinued
0.7447	Intermediate Similarity	NPD4749	Approved
0.7434	Intermediate Similarity	NPD6190	Approved
0.7432	Intermediate Similarity	NPD4536	Approved
0.7432	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4538	Approved
0.7425	Intermediate Similarity	NPD7685	Pre-registration
0.7419	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5403	Approved
0.7417	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4340	Discontinued
0.7405	Intermediate Similarity	NPD6801	Discontinued
0.7365	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6653	Approved
0.7362	Intermediate Similarity	NPD3787	Discontinued
0.7361	Intermediate Similarity	NPD3018	Phase 2
0.7358	Intermediate Similarity	NPD2801	Approved
0.7358	Intermediate Similarity	NPD7819	Suspended
0.7349	Intermediate Similarity	NPD5844	Phase 1
0.7342	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6799	Approved
0.7333	Intermediate Similarity	NPD7843	Approved
0.7333	Intermediate Similarity	NPD5535	Approved
0.7324	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3705	Approved
0.7299	Intermediate Similarity	NPD7157	Approved
0.7297	Intermediate Similarity	NPD6355	Discontinued
0.7293	Intermediate Similarity	NPD2684	Approved
0.729	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5401	Approved
0.7285	Intermediate Similarity	NPD5763	Approved
0.7285	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5762	Approved
0.7279	Intermediate Similarity	NPD4062	Phase 3
0.7267	Intermediate Similarity	NPD5960	Phase 3
0.7267	Intermediate Similarity	NPD7033	Discontinued
0.7267	Intermediate Similarity	NPD5588	Approved
0.7255	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3750	Approved
0.7237	Intermediate Similarity	NPD1549	Phase 2
0.7235	Intermediate Similarity	NPD8313	Approved
0.7235	Intermediate Similarity	NPD8312	Approved
0.7234	Intermediate Similarity	NPD3496	Discontinued
0.7233	Intermediate Similarity	NPD7411	Suspended
0.723	Intermediate Similarity	NPD4140	Approved
0.7226	Intermediate Similarity	NPD1511	Approved
0.7219	Intermediate Similarity	NPD1551	Phase 2
0.7218	Intermediate Similarity	NPD290	Approved
0.7218	Intermediate Similarity	NPD1358	Approved
0.7214	Intermediate Similarity	NPD5585	Approved
0.7186	Intermediate Similarity	NPD3751	Discontinued
0.7181	Intermediate Similarity	NPD230	Phase 1
0.7179	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3536	Discontinued
0.7163	Intermediate Similarity	NPD1778	Approved
0.716	Intermediate Similarity	NPD3882	Suspended
0.7154	Intermediate Similarity	NPD1242	Phase 1
0.7153	Intermediate Similarity	NPD3225	Approved
0.7143	Intermediate Similarity	NPD968	Approved
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1512	Approved
0.7133	Intermediate Similarity	NPD1608	Approved
0.7115	Intermediate Similarity	NPD7212	Phase 2
0.7115	Intermediate Similarity	NPD7213	Phase 3
0.7105	Intermediate Similarity	NPD6100	Approved
0.7105	Intermediate Similarity	NPD6032	Approved
0.7105	Intermediate Similarity	NPD6099	Approved
0.7099	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7447	Phase 1
0.7063	Intermediate Similarity	NPD4678	Approved
0.7063	Intermediate Similarity	NPD4675	Approved
0.7063	Intermediate Similarity	NPD1535	Discovery
0.7063	Intermediate Similarity	NPD6599	Discontinued
0.7055	Intermediate Similarity	NPD7768	Phase 2
0.7055	Intermediate Similarity	NPD6584	Phase 3
0.7052	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6671	Approved
0.7048	Intermediate Similarity	NPD6232	Discontinued
0.7044	Intermediate Similarity	NPD3687	Approved
0.7044	Intermediate Similarity	NPD3686	Approved
0.7042	Intermediate Similarity	NPD5846	Approved
0.7042	Intermediate Similarity	NPD5125	Phase 3
0.7042	Intermediate Similarity	NPD6516	Phase 2
0.7042	Intermediate Similarity	NPD5126	Approved
0.7039	Intermediate Similarity	NPD4108	Discontinued
0.7034	Intermediate Similarity	NPD8651	Approved
0.7033	Intermediate Similarity	NPD7680	Approved
0.7025	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1894	Discontinued
0.7015	Intermediate Similarity	NPD3134	Approved
0.7014	Intermediate Similarity	NPD1481	Phase 2
0.7013	Intermediate Similarity	NPD2424	Discontinued
0.7013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD228	Approved
0.7006	Intermediate Similarity	NPD4357	Discontinued
0.6994	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2796	Approved
0.6993	Remote Similarity	NPD2935	Discontinued
0.6988	Remote Similarity	NPD6959	Discontinued
0.6986	Remote Similarity	NPD2797	Approved
0.6977	Remote Similarity	NPD7549	Discontinued
0.6971	Remote Similarity	NPD6842	Approved
0.6971	Remote Similarity	NPD6841	Approved
0.6971	Remote Similarity	NPD6843	Phase 3
0.6968	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4359	Approved
0.6964	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1933	Approved
0.6954	Remote Similarity	NPD5735	Approved
0.695	Remote Similarity	NPD5536	Phase 2
0.6946	Remote Similarity	NPD7229	Phase 3
0.6939	Remote Similarity	NPD5647	Approved
0.6939	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2977	Approved
0.6933	Remote Similarity	NPD2978	Approved
0.6928	Remote Similarity	NPD4666	Phase 3
0.6928	Remote Similarity	NPD1510	Phase 2
0.6928	Remote Similarity	NPD5677	Discontinued
0.6928	Remote Similarity	NPD3748	Approved
0.6923	Remote Similarity	NPD17	Approved
0.6923	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4110	Phase 3
0.6923	Remote Similarity	NPD4535	Phase 3
0.6923	Remote Similarity	NPD7473	Discontinued
0.6918	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6971	Discontinued
0.6906	Remote Similarity	NPD5283	Phase 1
0.6903	Remote Similarity	NPD4534	Discontinued
0.6897	Remote Similarity	NPD2231	Phase 2
0.6897	Remote Similarity	NPD2235	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