NPASS Compound

Structure

CID200988 OpenBabel06191715592D 26 27 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 -6.0622 -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 -6.0622 -0.5000 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 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 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 -0.8660 1.5000 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 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 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 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 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 -9.5263 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 0.8660 -0.5000 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 15 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 16 1 0 0 0 0 6 10 1 0 0 0 0 6 16 2 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 17 2 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 15 26 1 0 0 0 0 18 23 1 0 0 0 0 19 5 1 6 0 0 0 19 26 1 0 0 0 0 20 21 2 0 0 0 0 20 24 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.18
Volume:	380.155
LogP:	3.686
LogD:	3.518
LogS:	-3.374
# Rotatable Bonds:	10
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.357
Synthetic Accessibility Score:	2.695
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.808
MDCK Permeability:	2.538246917538345e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	97.69108581542969%
Volume Distribution (VD):	0.728
Pgp-substrate:	2.2958829402923584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.665
CYP1A2-substrate:	0.251
CYP2C19-inhibitor:	0.868
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.612
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.959
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.374
CYP3A4-substrate:	0.235

ADMET: Excretion

Clearance (CL):	10.244
Half-life (T1/2):	0.936

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.307
Drug-inuced Liver Injury (DILI):	0.081
AMES Toxicity:	0.288
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.948
Carcinogencity:	0.38
Eye Corrosion:	0.164
Eye Irritation:	0.953
Respiratory Toxicity:	0.185

Download Data

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

Natural Product: NPC200988

Natural Product ID:	NPC200988
*Common Name:**	(3R)-3-Acetoxy-1-(3,4-Dihydroxyphenyl)-7-(4-Hydroxyphenyl)Heptane
IUPAC Name:	[(3R)-1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)heptan-3-yl] acetate
Synonyms:
Standard InCHIKey:	FNZIZWQXFYAOOE-LJQANCHMSA-N
Standard InCHI:	InChI=1S/C21H26O5/c1-15(22)26-19(12-8-17-9-13-20(24)21(25)14-17)5-3-2-4-16-6-10-18(23)11-7-16/h6-7,9-11,13-14,19,23-25H,2-5,8,12H2,1H3/t19-/m1/s1
SMILES:	CC(=O)O[C@H](CCCCc1ccc(cc1)O)CCc1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1270154
PubChem CID:	49832001
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	28490.0	nM	PMID[523502]

☑ 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 NPC200988 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	217
0.1-0.2	1120
0.2-0.3	3235
0.3-0.4	9564
0.4-0.5	10053
0.5-0.6	6505
0.6-0.7	8554
0.7-0.8	3081
0.8-0.85	294
0.85-0.9	50
0.9-0.95	15
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC175799
1.0	High Similarity	NPC610
1.0	High Similarity	NPC145023
0.9909	High Similarity	NPC86198
0.982	High Similarity	NPC109371
0.982	High Similarity	NPC470214
0.982	High Similarity	NPC470215
0.982	High Similarity	NPC70084
0.9474	High Similarity	NPC470848
0.9474	High Similarity	NPC470849
0.9298	High Similarity	NPC263386
0.9298	High Similarity	NPC141791
0.9211	High Similarity	NPC309434
0.9182	High Similarity	NPC79793
0.9182	High Similarity	NPC174096
0.9182	High Similarity	NPC226401
0.9182	High Similarity	NPC120982
0.9182	High Similarity	NPC147634
0.9107	High Similarity	NPC264558
0.9099	High Similarity	NPC257430
0.9099	High Similarity	NPC179002
0.9099	High Similarity	NPC187583
0.9091	High Similarity	NPC62258
0.9091	High Similarity	NPC55617
0.906	High Similarity	NPC147654
0.906	High Similarity	NPC472271
0.9043	High Similarity	NPC275519
0.9043	High Similarity	NPC203124
0.9035	High Similarity	NPC281277
0.9009	High Similarity	NPC63345
0.8974	High Similarity	NPC98305
0.8947	High Similarity	NPC233669
0.8919	High Similarity	NPC228343
0.8919	High Similarity	NPC254833
0.886	High Similarity	NPC261453
0.886	High Similarity	NPC328593
0.886	High Similarity	NPC120280
0.886	High Similarity	NPC33749
0.8843	High Similarity	NPC213552
0.8843	High Similarity	NPC120225
0.8833	High Similarity	NPC85565
0.8807	High Similarity	NPC471511
0.8783	High Similarity	NPC474967
0.8772	High Similarity	NPC95381
0.8772	High Similarity	NPC148969
0.8761	High Similarity	NPC297657
0.876	High Similarity	NPC289459
0.8729	High Similarity	NPC265454
0.8729	High Similarity	NPC34634
0.8678	High Similarity	NPC288945
0.8678	High Similarity	NPC246704
0.8655	High Similarity	NPC207613
0.8632	High Similarity	NPC278652
0.8632	High Similarity	NPC65791
0.8629	High Similarity	NPC83062
0.8596	High Similarity	NPC226250
0.8583	High Similarity	NPC343720
0.8583	High Similarity	NPC473853
0.8583	High Similarity	NPC322332
0.8583	High Similarity	NPC113865
0.8583	High Similarity	NPC67247
0.8583	High Similarity	NPC54872
0.8583	High Similarity	NPC470212
0.8583	High Similarity	NPC324571
0.8583	High Similarity	NPC312675
0.8583	High Similarity	NPC262156
0.8583	High Similarity	NPC184651
0.8559	High Similarity	NPC239291
0.8559	High Similarity	NPC470626
0.8545	High Similarity	NPC196479
0.8537	High Similarity	NPC118584
0.8534	High Similarity	NPC217472
0.8532	High Similarity	NPC223393
0.8525	High Similarity	NPC20443
0.8525	High Similarity	NPC146886
0.8525	High Similarity	NPC60517
0.8522	High Similarity	NPC131530
0.8512	High Similarity	NPC86900
0.8509	High Similarity	NPC222084
0.8509	High Similarity	NPC183700
0.8504	High Similarity	NPC168799
0.8504	High Similarity	NPC155209
0.8492	Intermediate Similarity	NPC198388
0.8482	Intermediate Similarity	NPC477814
0.8482	Intermediate Similarity	NPC1786
0.8482	Intermediate Similarity	NPC1075
0.8482	Intermediate Similarity	NPC294902
0.848	Intermediate Similarity	NPC30174
0.848	Intermediate Similarity	NPC241354
0.8475	Intermediate Similarity	NPC293619
0.8455	Intermediate Similarity	NPC110764
0.8455	Intermediate Similarity	NPC280767
0.8455	Intermediate Similarity	NPC67951
0.845	Intermediate Similarity	NPC471988
0.8448	Intermediate Similarity	NPC471485
0.8443	Intermediate Similarity	NPC317769
0.8443	Intermediate Similarity	NPC473451
0.8443	Intermediate Similarity	NPC31344
0.8443	Intermediate Similarity	NPC471693
0.8443	Intermediate Similarity	NPC306100
0.8438	Intermediate Similarity	NPC300776
0.8438	Intermediate Similarity	NPC5310
0.8438	Intermediate Similarity	NPC4982
0.8438	Intermediate Similarity	NPC106406
0.8438	Intermediate Similarity	NPC176814
0.8438	Intermediate Similarity	NPC135127
0.8438	Intermediate Similarity	NPC68779
0.843	Intermediate Similarity	NPC290451
0.843	Intermediate Similarity	NPC127389
0.8425	Intermediate Similarity	NPC25581
0.8425	Intermediate Similarity	NPC61
0.8425	Intermediate Similarity	NPC18074
0.8425	Intermediate Similarity	NPC5419
0.8417	Intermediate Similarity	NPC227217
0.8417	Intermediate Similarity	NPC117780
0.8417	Intermediate Similarity	NPC165133
0.8417	Intermediate Similarity	NPC95614
0.8417	Intermediate Similarity	NPC242885
0.8417	Intermediate Similarity	NPC232316
0.8417	Intermediate Similarity	NPC56214
0.8403	Intermediate Similarity	NPC63126
0.8403	Intermediate Similarity	NPC206205
0.84	Intermediate Similarity	NPC478215
0.84	Intermediate Similarity	NPC110313
0.839	Intermediate Similarity	NPC61062
0.839	Intermediate Similarity	NPC277394
0.839	Intermediate Similarity	NPC299252
0.8387	Intermediate Similarity	NPC94179
0.8385	Intermediate Similarity	NPC281780
0.8374	Intermediate Similarity	NPC257682
0.8374	Intermediate Similarity	NPC131747
0.8374	Intermediate Similarity	NPC469568
0.8374	Intermediate Similarity	NPC146355
0.8364	Intermediate Similarity	NPC294741
0.8362	Intermediate Similarity	NPC51698
0.8361	Intermediate Similarity	NPC85488
0.8349	Intermediate Similarity	NPC109955
0.8347	Intermediate Similarity	NPC204466
0.8347	Intermediate Similarity	NPC470414
0.8346	Intermediate Similarity	NPC318799
0.8333	Intermediate Similarity	NPC241634
0.8333	Intermediate Similarity	NPC311595
0.8333	Intermediate Similarity	NPC24474
0.8333	Intermediate Similarity	NPC310338
0.8333	Intermediate Similarity	NPC281298
0.832	Intermediate Similarity	NPC79715
0.832	Intermediate Similarity	NPC108659
0.832	Intermediate Similarity	NPC231607
0.832	Intermediate Similarity	NPC264900
0.8319	Intermediate Similarity	NPC325295
0.8319	Intermediate Similarity	NPC76308
0.8319	Intermediate Similarity	NPC164386
0.8319	Intermediate Similarity	NPC92623
0.8319	Intermediate Similarity	NPC135464
0.8308	Intermediate Similarity	NPC154485
0.8308	Intermediate Similarity	NPC120852
0.8308	Intermediate Similarity	NPC90431
0.8308	Intermediate Similarity	NPC471872
0.8308	Intermediate Similarity	NPC476699
0.8306	Intermediate Similarity	NPC148627
0.8306	Intermediate Similarity	NPC53305
0.8306	Intermediate Similarity	NPC197832
0.8306	Intermediate Similarity	NPC194519
0.8306	Intermediate Similarity	NPC257589
0.8304	Intermediate Similarity	NPC12278
0.8304	Intermediate Similarity	NPC120719
0.8304	Intermediate Similarity	NPC52087
0.8295	Intermediate Similarity	NPC34293
0.8295	Intermediate Similarity	NPC287597
0.8295	Intermediate Similarity	NPC886
0.8293	Intermediate Similarity	NPC280704
0.8293	Intermediate Similarity	NPC285345
0.8293	Intermediate Similarity	NPC212541
0.8288	Intermediate Similarity	NPC91461
0.8288	Intermediate Similarity	NPC7686
0.8288	Intermediate Similarity	NPC40258
0.8279	Intermediate Similarity	NPC38996
0.8279	Intermediate Similarity	NPC70752
0.8279	Intermediate Similarity	NPC160380
0.8276	Intermediate Similarity	NPC268032
0.8273	Intermediate Similarity	NPC78119
0.8273	Intermediate Similarity	NPC51333
0.8273	Intermediate Similarity	NPC131587
0.8273	Intermediate Similarity	NPC216468
0.8273	Intermediate Similarity	NPC132078
0.8268	Intermediate Similarity	NPC319282
0.8268	Intermediate Similarity	NPC275724
0.8268	Intermediate Similarity	NPC244246
0.8268	Intermediate Similarity	NPC217052
0.8268	Intermediate Similarity	NPC32626
0.8268	Intermediate Similarity	NPC123196
0.8268	Intermediate Similarity	NPC215941
0.8268	Intermediate Similarity	NPC329344
0.8268	Intermediate Similarity	NPC65935
0.8268	Intermediate Similarity	NPC237506
0.8268	Intermediate Similarity	NPC311419
0.8268	Intermediate Similarity	NPC137427
0.8264	Intermediate Similarity	NPC202474
0.8264	Intermediate Similarity	NPC2058
0.8254	Intermediate Similarity	NPC226661

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 NPC200988 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	792
0.2-0.3	1467
0.3-0.4	2619
0.4-0.5	2117
0.5-0.6	1128
0.6-0.7	722
0.7-0.8	113
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8919	High Similarity	NPD3021	Approved
0.8919	High Similarity	NPD3022	Approved
0.8182	Intermediate Similarity	NPD7266	Discontinued
0.8165	Intermediate Similarity	NPD2859	Approved
0.8165	Intermediate Similarity	NPD2860	Approved
0.8108	Intermediate Similarity	NPD3020	Approved
0.8073	Intermediate Similarity	NPD2934	Approved
0.8073	Intermediate Similarity	NPD2933	Approved
0.8047	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD826	Approved
0.8	Intermediate Similarity	NPD825	Approved
0.8	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4060	Phase 1
0.7966	Intermediate Similarity	NPD228	Approved
0.7891	Intermediate Similarity	NPD5736	Approved
0.7868	Intermediate Similarity	NPD8166	Discontinued
0.7833	Intermediate Similarity	NPD5283	Phase 1
0.7681	Intermediate Similarity	NPD6190	Approved
0.7674	Intermediate Similarity	NPD258	Approved
0.7674	Intermediate Similarity	NPD257	Approved
0.7669	Intermediate Similarity	NPD555	Phase 2
0.7652	Intermediate Similarity	NPD6663	Approved
0.7634	Intermediate Similarity	NPD7095	Approved
0.7603	Intermediate Similarity	NPD5535	Approved
0.7594	Intermediate Similarity	NPD1613	Approved
0.7594	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6798	Discontinued
0.7559	Intermediate Similarity	NPD3092	Approved
0.7552	Intermediate Similarity	NPD3455	Phase 2
0.7537	Intermediate Similarity	NPD6355	Discontinued
0.7522	Intermediate Similarity	NPD844	Approved
0.752	Intermediate Similarity	NPD3091	Approved
0.7519	Intermediate Similarity	NPD259	Phase 1
0.7482	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD4110	Phase 3
0.748	Intermediate Similarity	NPD3847	Discontinued
0.748	Intermediate Similarity	NPD2629	Approved
0.7463	Intermediate Similarity	NPD3059	Approved
0.7463	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3061	Approved
0.7463	Intermediate Similarity	NPD3620	Phase 2
0.7463	Intermediate Similarity	NPD3062	Approved
0.7462	Intermediate Similarity	NPD3053	Approved
0.7462	Intermediate Similarity	NPD3055	Approved
0.7462	Intermediate Similarity	NPD3094	Phase 2
0.7459	Intermediate Similarity	NPD9379	Approved
0.7459	Intermediate Similarity	NPD9377	Approved
0.744	Intermediate Similarity	NPD5536	Phase 2
0.7424	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD2684	Approved
0.7414	Intermediate Similarity	NPD1242	Phase 1
0.7407	Intermediate Similarity	NPD230	Phase 1
0.7402	Intermediate Similarity	NPD4626	Approved
0.7402	Intermediate Similarity	NPD9381	Approved
0.7402	Intermediate Similarity	NPD9384	Approved
0.7391	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD4062	Phase 3
0.7388	Intermediate Similarity	NPD6233	Phase 2
0.7385	Intermediate Similarity	NPD5311	Approved
0.7385	Intermediate Similarity	NPD5310	Approved
0.7353	Intermediate Similarity	NPD5314	Approved
0.7348	Intermediate Similarity	NPD9569	Approved
0.7348	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD3496	Discontinued
0.7333	Intermediate Similarity	NPD4140	Approved
0.7333	Intermediate Similarity	NPD1358	Approved
0.7324	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD1357	Approved
0.7323	Intermediate Similarity	NPD5691	Approved
0.7317	Intermediate Similarity	NPD7843	Approved
0.7308	Intermediate Similarity	NPD9622	Approved
0.7308	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD288	Approved
0.7295	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD7157	Approved
0.728	Intermediate Similarity	NPD4198	Discontinued
0.7279	Intermediate Similarity	NPD275	Approved
0.7279	Intermediate Similarity	NPD274	Approved
0.7273	Intermediate Similarity	NPD6584	Phase 3
0.7266	Intermediate Similarity	NPD3019	Approved
0.7266	Intermediate Similarity	NPD2932	Approved
0.7266	Intermediate Similarity	NPD3095	Discontinued
0.7265	Intermediate Similarity	NPD3028	Approved
0.7265	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD1283	Approved
0.725	Intermediate Similarity	NPD3134	Approved
0.7248	Intermediate Similarity	NPD111	Approved
0.7244	Intermediate Similarity	NPD1894	Discontinued
0.7234	Intermediate Similarity	NPD4628	Phase 3
0.7218	Intermediate Similarity	NPD2861	Phase 2
0.7206	Intermediate Similarity	NPD943	Approved
0.7203	Intermediate Similarity	NPD846	Approved
0.7203	Intermediate Similarity	NPD940	Approved
0.7194	Intermediate Similarity	NPD6032	Approved
0.7194	Intermediate Similarity	NPD2935	Discontinued
0.7194	Intermediate Similarity	NPD9570	Approved
0.7188	Intermediate Similarity	NPD5585	Approved
0.7185	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD7635	Approved
0.7154	Intermediate Similarity	NPD1535	Discovery
0.7152	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD9620	Approved
0.7143	Intermediate Similarity	NPD9619	Approved
0.7143	Intermediate Similarity	NPD6671	Approved
0.7143	Intermediate Similarity	NPD9621	Approved
0.7143	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD5762	Approved
0.7133	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD2228	Approved
0.712	Intermediate Similarity	NPD2234	Approved
0.712	Intermediate Similarity	NPD2229	Approved
0.7114	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD9537	Phase 1
0.7111	Intermediate Similarity	NPD9536	Phase 1
0.7109	Intermediate Similarity	NPD9545	Approved
0.7107	Intermediate Similarity	NPD968	Approved
0.7101	Intermediate Similarity	NPD6653	Approved
0.7099	Intermediate Similarity	NPD9269	Phase 2
0.7099	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1481	Phase 2
0.7099	Intermediate Similarity	NPD1608	Approved
0.7092	Intermediate Similarity	NPD4534	Discontinued
0.709	Intermediate Similarity	NPD9494	Approved
0.708	Intermediate Similarity	NPD2979	Phase 3
0.708	Intermediate Similarity	NPD1558	Phase 1
0.7073	Intermediate Similarity	NPD4750	Phase 3
0.7073	Intermediate Similarity	NPD1792	Phase 2
0.7071	Intermediate Similarity	NPD2438	Suspended
0.7069	Intermediate Similarity	NPD1809	Phase 2
0.7059	Intermediate Similarity	NPD597	Approved
0.7059	Intermediate Similarity	NPD601	Approved
0.7059	Intermediate Similarity	NPD598	Approved
0.7059	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3764	Approved
0.7054	Intermediate Similarity	NPD4093	Discontinued
0.705	Intermediate Similarity	NPD7097	Phase 1
0.7049	Intermediate Similarity	NPD2342	Discontinued
0.7047	Intermediate Similarity	NPD1934	Approved
0.7045	Intermediate Similarity	NPD6583	Phase 3
0.7045	Intermediate Similarity	NPD6582	Phase 2
0.7043	Intermediate Similarity	NPD845	Approved
0.7042	Intermediate Similarity	NPD3060	Approved
0.7037	Intermediate Similarity	NPD4908	Phase 1
0.7029	Intermediate Similarity	NPD4340	Discontinued
0.7023	Intermediate Similarity	NPD3705	Approved
0.7023	Intermediate Similarity	NPD1281	Approved
0.7023	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD255	Approved
0.7008	Intermediate Similarity	NPD256	Approved
0.7007	Intermediate Similarity	NPD1136	Approved
0.7007	Intermediate Similarity	NPD1130	Approved
0.7007	Intermediate Similarity	NPD2674	Phase 3
0.7007	Intermediate Similarity	NPD1653	Approved
0.7007	Intermediate Similarity	NPD1132	Approved
0.7	Intermediate Similarity	NPD6516	Phase 2
0.7	Intermediate Similarity	NPD1778	Approved
0.7	Intermediate Similarity	NPD5846	Approved
0.7	Intermediate Similarity	NPD4059	Approved
0.6992	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5163	Phase 2
0.6984	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD817	Approved
0.6978	Remote Similarity	NPD823	Approved
0.6972	Remote Similarity	NPD5958	Discontinued
0.6967	Remote Similarity	NPD1444	Approved
0.6967	Remote Similarity	NPD1445	Approved
0.696	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6346	Approved
0.6949	Remote Similarity	NPD9495	Approved
0.694	Remote Similarity	NPD2797	Approved
0.694	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5451	Approved
0.6934	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD37	Approved
0.6929	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4162	Approved
0.6923	Remote Similarity	NPD1651	Approved
0.6918	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3536	Discontinued
0.6917	Remote Similarity	NPD2982	Phase 2
0.6917	Remote Similarity	NPD2983	Phase 2
0.6917	Remote Similarity	NPD4659	Approved
0.6917	Remote Similarity	NPD4359	Approved
0.6912	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD290	Approved
0.6908	Remote Similarity	NPD4965	Approved
0.6908	Remote Similarity	NPD4966	Approved
0.6908	Remote Similarity	NPD4967	Phase 2
0.6906	Remote Similarity	NPD5735	Approved
0.6894	Remote Similarity	NPD1610	Phase 2
0.6894	Remote Similarity	NPD422	Phase 1
0.6894	Remote Similarity	NPD1611	Approved
0.6892	Remote Similarity	NPD3686	Approved
0.6892	Remote Similarity	NPD3687	Approved
0.6887	Remote Similarity	NPD5563	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