NPASS Compound

Structure

NPC116104 OpenBabel07101718312D 37 40 0 0 1 0 0 0 0 0999 V2000 -3.4263 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 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 6.0622 1.5000 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 7.7942 0.5000 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 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 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 6.0622 0.5000 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 1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 2 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 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 2 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 -0.0000 2.0000 0.0000 C 0 0 1 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 -2.6831 0.3090 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 -2.9921 -2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -1.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 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 3.4641 2.0000 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 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 33 1 0 0 0 0 3 6 1 0 0 0 0 3 13 2 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 14 1 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 25 1 0 0 0 0 10 34 1 0 0 0 0 11 16 1 0 0 0 0 11 24 1 0 0 0 0 12 35 1 0 0 0 0 14 33 1 0 0 0 0 15 12 1 1 0 0 0 15 18 1 0 0 0 0 15 36 1 0 0 0 0 16 25 1 6 0 0 0 16 26 1 0 0 0 0 17 27 2 0 0 0 0 17 35 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 29 1 1 0 0 0 20 22 1 0 0 0 0 20 30 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 1 0 0 0 21 25 1 0 0 0 0 22 36 1 0 0 0 0 22 37 1 1 0 0 0 23 34 1 0 0 0 0 23 37 1 6 0 0 0 24 1 1 1 0 0 0 24 31 1 0 0 0 0 25 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.19
Volume:	496.394
LogP:	0.945
LogD:	-0.106
LogS:	-3.096
# Rotatable Bonds:	8
TPSA:	184.6
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.185
Synthetic Accessibility Score:	4.824
Fsp3:	0.56
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.214
MDCK Permeability:	9.211233555106446e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.944
20% Bioavailability (F20%):	0.275
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	59.837974548339844%
Volume Distribution (VD):	0.38
Pgp-substrate:	33.715152740478516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.52
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.206
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.332
CYP3A4-substrate:	0.111

ADMET: Excretion

Clearance (CL):	1.748
Half-life (T1/2):	0.652

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.335
Drug-inuced Liver Injury (DILI):	0.082
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.275
Skin Sensitization:	0.131
Carcinogencity:	0.516
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC116104

Natural Product ID:	NPC116104
*Common Name:**	6'-O-Z-Para-Methoxycinnamoylharpagide
IUPAC Name:	[(2R,3S,4S,5R,6S)-6-[[(1S,4aS,5R,7S,7aR)-4a,5,7-trihydroxy-7-methyl-1,5,6,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl (Z)-3-(4-methoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	FLGNDYLGJFFGQZ-DGJQUCGESA-N
Standard InCHI:	InChI=1S/C25H32O12/c1-24(31)11-16(26)25(32)9-10-34-23(21(24)25)37-22-20(30)19(29)18(28)15(36-22)12-35-17(27)8-5-13-3-6-14(33-2)7-4-13/h3-10,15-16,18-23,26,28-32H,11-12H2,1-2H3/b8-5-/t15-,16-,18-,19+,20-,21-,22+,23+,24+,25-/m1/s1
SMILES:	C[C@@]1(C[C@H]([C@@]2(C=CO[C@H]([C@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)/C=Cc2ccc(cc2)OC)O1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465250
PubChem CID:	10896666
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-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
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	roots	n.a.	n.a.	PMID[12444706]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6541	Scrophularia buergeriana	Species	Scrophulariaceae	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	3

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Activity	=	46.6	%	PMID[522925]
NPT2	Others	Unspecified	Activity	=	47.6	%	PMID[522925]
NPT2	Others	Unspecified	Activity	=	33.3	%	PMID[522925]

☑ 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 NPC116104 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	291
0.1-0.2	1224
0.2-0.3	3006
0.3-0.4	7048
0.4-0.5	10755
0.5-0.6	8923
0.6-0.7	9561
0.7-0.8	1686
0.8-0.85	143
0.85-0.9	38
0.9-0.95	14
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC263397
1.0	High Similarity	NPC88754
1.0	High Similarity	NPC237872
1.0	High Similarity	NPC302286
0.9783	High Similarity	NPC37838
0.9638	High Similarity	NPC478240
0.9559	High Similarity	NPC49597
0.9507	High Similarity	NPC147224
0.9366	High Similarity	NPC308178
0.9306	High Similarity	NPC269914
0.9306	High Similarity	NPC478249
0.9281	High Similarity	NPC46644
0.922	High Similarity	NPC251062
0.922	High Similarity	NPC184464
0.9178	High Similarity	NPC478241
0.9178	High Similarity	NPC229548
0.9178	High Similarity	NPC89693
0.9041	High Similarity	NPC475379
0.9014	High Similarity	NPC186296
0.9014	High Similarity	NPC475213
0.9014	High Similarity	NPC152796
0.9007	High Similarity	NPC137501
0.9007	High Similarity	NPC154262
0.9007	High Similarity	NPC159387
0.9007	High Similarity	NPC7518
0.8993	High Similarity	NPC478248
0.8986	High Similarity	NPC478232
0.894	High Similarity	NPC478265
0.8905	High Similarity	NPC254819
0.8904	High Similarity	NPC478234
0.8897	High Similarity	NPC18789
0.8844	High Similarity	NPC117346
0.8844	High Similarity	NPC240592
0.8815	High Similarity	NPC276047
0.8815	High Similarity	NPC267733
0.8776	High Similarity	NPC478236
0.8776	High Similarity	NPC96599
0.8767	High Similarity	NPC473149
0.8759	High Similarity	NPC295970
0.8725	High Similarity	NPC194705
0.8699	High Similarity	NPC474234
0.8693	High Similarity	NPC474936
0.869	High Similarity	NPC296659
0.869	High Similarity	NPC202391
0.8667	High Similarity	NPC145287
0.8658	High Similarity	NPC289021
0.8658	High Similarity	NPC158546
0.8633	High Similarity	NPC475824
0.8627	High Similarity	NPC179914
0.8618	High Similarity	NPC478266
0.8613	High Similarity	NPC106677
0.8601	High Similarity	NPC220936
0.8601	High Similarity	NPC31745
0.8581	High Similarity	NPC476011
0.8581	High Similarity	NPC206815
0.8543	High Similarity	NPC469699
0.8535	High Similarity	NPC301910
0.8535	High Similarity	NPC130730
0.85	High Similarity	NPC478255
0.85	High Similarity	NPC225384
0.85	High Similarity	NPC246869
0.85	High Similarity	NPC138777
0.8497	Intermediate Similarity	NPC475378
0.8493	Intermediate Similarity	NPC293154
0.8483	Intermediate Similarity	NPC476442
0.8483	Intermediate Similarity	NPC215512
0.8481	Intermediate Similarity	NPC208818
0.8478	Intermediate Similarity	NPC471882
0.8478	Intermediate Similarity	NPC45224
0.8478	Intermediate Similarity	NPC471881
0.8478	Intermediate Similarity	NPC156692
0.8478	Intermediate Similarity	NPC173150
0.8478	Intermediate Similarity	NPC175333
0.8478	Intermediate Similarity	NPC35288
0.8477	Intermediate Similarity	NPC203664
0.8462	Intermediate Similarity	NPC166180
0.8451	Intermediate Similarity	NPC169398
0.8435	Intermediate Similarity	NPC473281
0.8435	Intermediate Similarity	NPC110063
0.8435	Intermediate Similarity	NPC77922
0.8431	Intermediate Similarity	NPC475484
0.8421	Intermediate Similarity	NPC229354
0.8418	Intermediate Similarity	NPC282551
0.8417	Intermediate Similarity	NPC225307
0.8417	Intermediate Similarity	NPC146540
0.8406	Intermediate Similarity	NPC252114
0.8406	Intermediate Similarity	NPC61181
0.8406	Intermediate Similarity	NPC471157
0.8389	Intermediate Similarity	NPC97240
0.8382	Intermediate Similarity	NPC52097
0.8369	Intermediate Similarity	NPC235294
0.8369	Intermediate Similarity	NPC46137
0.8367	Intermediate Similarity	NPC469367
0.8357	Intermediate Similarity	NPC253595
0.8355	Intermediate Similarity	NPC478235
0.8345	Intermediate Similarity	NPC288416
0.8345	Intermediate Similarity	NPC226005
0.8345	Intermediate Similarity	NPC103533
0.8333	Intermediate Similarity	NPC220282
0.8333	Intermediate Similarity	NPC103409
0.8333	Intermediate Similarity	NPC169510
0.8333	Intermediate Similarity	NPC83218
0.8333	Intermediate Similarity	NPC157554
0.8333	Intermediate Similarity	NPC37468
0.8333	Intermediate Similarity	NPC472132
0.8333	Intermediate Similarity	NPC138993
0.8333	Intermediate Similarity	NPC126991
0.8313	Intermediate Similarity	NPC21956
0.8311	Intermediate Similarity	NPC63304
0.8309	Intermediate Similarity	NPC11724
0.8299	Intermediate Similarity	NPC140502
0.8276	Intermediate Similarity	NPC101686
0.8276	Intermediate Similarity	NPC469364
0.8276	Intermediate Similarity	NPC65262
0.8267	Intermediate Similarity	NPC296377
0.8267	Intermediate Similarity	NPC175275
0.8255	Intermediate Similarity	NPC34927
0.8255	Intermediate Similarity	NPC476382
0.8255	Intermediate Similarity	NPC287615
0.8255	Intermediate Similarity	NPC34587
0.8255	Intermediate Similarity	NPC252292
0.8255	Intermediate Similarity	NPC262182
0.8255	Intermediate Similarity	NPC83743
0.8255	Intermediate Similarity	NPC85624
0.8255	Intermediate Similarity	NPC100998
0.8255	Intermediate Similarity	NPC216819
0.825	Intermediate Similarity	NPC286809
0.8248	Intermediate Similarity	NPC476142
0.8243	Intermediate Similarity	NPC478239
0.8235	Intermediate Similarity	NPC478268
0.8235	Intermediate Similarity	NPC476872
0.8231	Intermediate Similarity	NPC186406
0.8224	Intermediate Similarity	NPC470934
0.8224	Intermediate Similarity	NPC188393
0.8219	Intermediate Similarity	NPC100389
0.8212	Intermediate Similarity	NPC95990
0.821	Intermediate Similarity	NPC470685
0.82	Intermediate Similarity	NPC119773
0.82	Intermediate Similarity	NPC475539
0.82	Intermediate Similarity	NPC474268
0.82	Intermediate Similarity	NPC143246
0.8194	Intermediate Similarity	NPC471029
0.8188	Intermediate Similarity	NPC471028
0.8188	Intermediate Similarity	NPC297342
0.8187	Intermediate Similarity	NPC475621
0.8176	Intermediate Similarity	NPC145319
0.8176	Intermediate Similarity	NPC157816
0.8176	Intermediate Similarity	NPC109990
0.8163	Intermediate Similarity	NPC202700
0.8158	Intermediate Similarity	NPC478242
0.8153	Intermediate Similarity	NPC469384
0.8146	Intermediate Similarity	NPC232992
0.8146	Intermediate Similarity	NPC471764
0.8146	Intermediate Similarity	NPC87950
0.8138	Intermediate Similarity	NPC263829
0.8138	Intermediate Similarity	NPC185778
0.8133	Intermediate Similarity	NPC475528
0.8133	Intermediate Similarity	NPC226722
0.8129	Intermediate Similarity	NPC287429
0.8125	Intermediate Similarity	NPC28637
0.8125	Intermediate Similarity	NPC254398
0.8113	Intermediate Similarity	NPC145847
0.8112	Intermediate Similarity	NPC281798
0.8108	Intermediate Similarity	NPC80098
0.8105	Intermediate Similarity	NPC35097
0.8105	Intermediate Similarity	NPC69367
0.8102	Intermediate Similarity	NPC198734
0.8102	Intermediate Similarity	NPC469412
0.8102	Intermediate Similarity	NPC269242
0.8095	Intermediate Similarity	NPC328273
0.8095	Intermediate Similarity	NPC171134
0.8095	Intermediate Similarity	NPC321638
0.8095	Intermediate Similarity	NPC321184
0.8092	Intermediate Similarity	NPC201148
0.8092	Intermediate Similarity	NPC215095
0.8092	Intermediate Similarity	NPC300262
0.8092	Intermediate Similarity	NPC261122
0.8092	Intermediate Similarity	NPC189631
0.8092	Intermediate Similarity	NPC28651
0.8092	Intermediate Similarity	NPC210611
0.8092	Intermediate Similarity	NPC192763
0.8092	Intermediate Similarity	NPC199311
0.8092	Intermediate Similarity	NPC80732
0.8092	Intermediate Similarity	NPC3460
0.8089	Intermediate Similarity	NPC286919
0.8089	Intermediate Similarity	NPC329997
0.8089	Intermediate Similarity	NPC475663
0.8082	Intermediate Similarity	NPC186418
0.8079	Intermediate Similarity	NPC473147
0.8079	Intermediate Similarity	NPC199928
0.8079	Intermediate Similarity	NPC476865
0.8071	Intermediate Similarity	NPC470510
0.8069	Intermediate Similarity	NPC471883
0.8067	Intermediate Similarity	NPC232228
0.8067	Intermediate Similarity	NPC194938
0.8067	Intermediate Similarity	NPC476867
0.8067	Intermediate Similarity	NPC292443
0.8056	Intermediate Similarity	NPC473285
0.8056	Intermediate Similarity	NPC473924
0.8054	Intermediate Similarity	NPC296643

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 NPC116104 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	735
0.2-0.3	1712
0.3-0.4	2787
0.4-0.5	2106
0.5-0.6	1196
0.6-0.7	339
0.7-0.8	36
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8385	Intermediate Similarity	NPD7685	Pre-registration
0.7973	Intermediate Similarity	NPD7266	Discontinued
0.7806	Intermediate Similarity	NPD1653	Approved
0.7786	Intermediate Similarity	NPD1091	Approved
0.7703	Intermediate Similarity	NPD6653	Approved
0.75	Intermediate Similarity	NPD5763	Approved
0.75	Intermediate Similarity	NPD5762	Approved
0.7448	Intermediate Similarity	NPD6362	Approved
0.7417	Intermediate Similarity	NPD7097	Phase 1
0.7403	Intermediate Similarity	NPD1652	Phase 2
0.74	Intermediate Similarity	NPD5124	Phase 1
0.74	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD8455	Phase 2
0.7333	Intermediate Similarity	NPD1358	Approved
0.7317	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5647	Approved
0.7273	Intermediate Similarity	NPD6005	Phase 3
0.7273	Intermediate Similarity	NPD6002	Phase 3
0.7273	Intermediate Similarity	NPD6004	Phase 3
0.7273	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD3134	Approved
0.7244	Intermediate Similarity	NPD4628	Phase 3
0.7241	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4140	Approved
0.7186	Intermediate Similarity	NPD7199	Phase 2
0.7178	Intermediate Similarity	NPD37	Approved
0.7176	Intermediate Similarity	NPD7228	Approved
0.7171	Intermediate Similarity	NPD5735	Approved
0.7171	Intermediate Similarity	NPD6355	Discontinued
0.7171	Intermediate Similarity	NPD4340	Discontinued
0.7152	Intermediate Similarity	NPD4965	Approved
0.7152	Intermediate Similarity	NPD4966	Approved
0.7152	Intermediate Similarity	NPD4967	Phase 2
0.7152	Intermediate Similarity	NPD5058	Phase 3
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7114	Intermediate Similarity	NPD2861	Phase 2
0.7107	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8127	Discontinued
0.7071	Intermediate Similarity	NPD7843	Approved
0.707	Intermediate Similarity	NPD6674	Discontinued
0.7066	Intermediate Similarity	NPD6234	Discontinued
0.7055	Intermediate Similarity	NPD3705	Approved
0.7055	Intermediate Similarity	NPD422	Phase 1
0.7042	Intermediate Similarity	NPD7157	Approved
0.7039	Intermediate Similarity	NPD6233	Phase 2
0.7035	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7054	Approved
0.7011	Intermediate Similarity	NPD6559	Discontinued
0.7	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD969	Suspended
0.6994	Remote Similarity	NPD7472	Approved
0.6981	Remote Similarity	NPD6190	Approved
0.698	Remote Similarity	NPD3094	Phase 2
0.6977	Remote Similarity	NPD3818	Discontinued
0.6966	Remote Similarity	NPD1357	Approved
0.6951	Remote Similarity	NPD7028	Phase 2
0.6951	Remote Similarity	NPD4380	Phase 2
0.6933	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD8313	Approved
0.6932	Remote Similarity	NPD8312	Approved
0.6914	Remote Similarity	NPD7251	Discontinued
0.6914	Remote Similarity	NPD6273	Approved
0.6914	Remote Similarity	NPD7240	Approved
0.6914	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3027	Phase 3
0.6908	Remote Similarity	NPD7095	Approved
0.6906	Remote Similarity	NPD2684	Approved
0.6905	Remote Similarity	NPD7075	Discontinued
0.6899	Remote Similarity	NPD2424	Discontinued
0.6897	Remote Similarity	NPD7074	Phase 3
0.689	Remote Similarity	NPD7458	Discontinued
0.6883	Remote Similarity	NPD4060	Phase 1
0.6883	Remote Similarity	NPD3620	Phase 2
0.6883	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7808	Phase 3
0.6871	Remote Similarity	NPD5403	Approved
0.6867	Remote Similarity	NPD6801	Discontinued
0.6867	Remote Similarity	NPD2797	Approved
0.6863	Remote Similarity	NPD6798	Discontinued
0.6863	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6797	Phase 2
0.6851	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4908	Phase 1
0.6835	Remote Similarity	NPD290	Approved
0.6826	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5125	Phase 3
0.6803	Remote Similarity	NPD5126	Approved
0.68	Remote Similarity	NPD3225	Approved
0.68	Remote Similarity	NPD8651	Approved
0.6795	Remote Similarity	NPD6353	Approved
0.6782	Remote Similarity	NPD7799	Discontinued
0.6781	Remote Similarity	NPD9545	Approved
0.6776	Remote Similarity	NPD5736	Approved
0.6774	Remote Similarity	NPD1613	Approved
0.6774	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3496	Discontinued
0.6753	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD3268	Approved
0.6752	Remote Similarity	NPD4538	Approved
0.6752	Remote Similarity	NPD4536	Approved
0.6752	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5401	Approved
0.6748	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5327	Phase 3
0.6713	Remote Similarity	NPD5535	Approved
0.6711	Remote Similarity	NPD4624	Approved
0.6711	Remote Similarity	NPD3092	Approved
0.6711	Remote Similarity	NPD1610	Phase 2
0.671	Remote Similarity	NPD4062	Phase 3
0.6709	Remote Similarity	NPD5588	Approved
0.6689	Remote Similarity	NPD4626	Approved
0.6687	Remote Similarity	NPD6799	Approved
0.6686	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD1548	Phase 1
0.6667	Remote Similarity	NPD7741	Discontinued
0.6646	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3764	Approved
0.6627	Remote Similarity	NPD5760	Phase 2
0.6627	Remote Similarity	NPD5761	Phase 2
0.6627	Remote Similarity	NPD7819	Suspended
0.6624	Remote Similarity	NPD1933	Approved
0.6623	Remote Similarity	NPD3685	Discontinued
0.6622	Remote Similarity	NPD5691	Approved
0.6607	Remote Similarity	NPD7411	Suspended
0.6607	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD4110	Phase 3
0.6605	Remote Similarity	NPD3750	Approved
0.6605	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5960	Phase 3
0.6604	Remote Similarity	NPD4108	Discontinued
0.6603	Remote Similarity	NPD6663	Approved
0.6591	Remote Similarity	NPD3751	Discontinued
0.6588	Remote Similarity	NPD3817	Phase 2
0.6584	Remote Similarity	NPD5958	Discontinued
0.6584	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7497	Discontinued
0.6571	Remote Similarity	NPD9697	Approved
0.6554	Remote Similarity	NPD5844	Phase 1
0.6548	Remote Similarity	NPD6599	Discontinued
0.6547	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3536	Discontinued
0.6545	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8434	Phase 2
0.6536	Remote Similarity	NPD987	Approved
0.6533	Remote Similarity	NPD3847	Discontinued
0.6525	Remote Similarity	NPD6685	Approved
0.6524	Remote Similarity	NPD6666	Approved
0.6524	Remote Similarity	NPD6667	Approved
0.6519	Remote Similarity	NPD230	Phase 1
0.6516	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6832	Phase 2
0.6513	Remote Similarity	NPD4749	Approved
0.651	Remote Similarity	NPD7503	Approved
0.651	Remote Similarity	NPD7999	Approved
0.651	Remote Similarity	NPD5585	Approved
0.6503	Remote Similarity	NPD6842	Approved
0.6503	Remote Similarity	NPD6841	Approved
0.6503	Remote Similarity	NPD6843	Phase 3
0.65	Remote Similarity	NPD7549	Discontinued
0.6497	Remote Similarity	NPD7930	Approved
0.6494	Remote Similarity	NPD2798	Approved
0.6492	Remote Similarity	NPD7435	Discontinued
0.6491	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD2415	Discontinued
0.6486	Remote Similarity	NPD5536	Phase 2
0.6481	Remote Similarity	NPD1549	Phase 2
0.6477	Remote Similarity	NPD7583	Approved
0.6474	Remote Similarity	NPD3180	Approved
0.6474	Remote Similarity	NPD3179	Approved
0.6471	Remote Similarity	NPD1934	Approved
0.6471	Remote Similarity	NPD1876	Approved
0.6467	Remote Similarity	NPD1778	Approved
0.6467	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6516	Phase 2
0.6467	Remote Similarity	NPD5846	Approved
0.6463	Remote Similarity	NPD6671	Approved
0.646	Remote Similarity	NPD5712	Approved
0.646	Remote Similarity	NPD2935	Discontinued
0.646	Remote Similarity	NPD2438	Suspended
0.6457	Remote Similarity	NPD3787	Discontinued
0.6456	Remote Similarity	NPD2238	Phase 2
0.6455	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7768	Phase 2
0.6452	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD1608	Approved
0.6447	Remote Similarity	NPD9717	Approved
0.6444	Remote Similarity	NPD6765	Approved
0.6444	Remote Similarity	NPD6764	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