NPASS Compound

Structure

CID114740 OpenBabel06191715472D 35 38 0 0 1 0 0 0 0 0999 V2000 3.4641 4.0000 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 -5.1962 -2.0000 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 -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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 3.4641 1.0000 0.0000 C 0 0 2 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 2.5981 1.5000 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 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 -1.7321 0.0000 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 2 30 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 31 1 0 0 0 0 8 1 1 1 0 0 0 8 15 1 0 0 0 0 8 32 1 0 0 0 0 9 10 1 0 0 0 0 10 33 1 0 0 0 0 11 12 2 0 0 0 0 11 30 1 0 0 0 0 12 34 1 0 0 0 0 13 7 1 6 0 0 0 13 16 1 0 0 0 0 13 35 1 0 0 0 0 14 23 2 0 0 0 0 14 33 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 6 0 0 0 16 18 1 0 0 0 0 16 25 1 1 0 0 0 17 19 1 0 0 0 0 17 26 1 1 0 0 0 18 20 1 0 0 0 0 18 27 1 6 0 0 0 19 21 1 0 0 0 0 19 28 1 1 0 0 0 20 22 1 0 0 0 0 20 29 1 1 0 0 0 21 31 1 6 0 0 0 21 32 1 0 0 0 0 22 34 1 6 0 0 0 22 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.15
Volume:	455.933
LogP:	-0.372
LogD:	-0.632
LogS:	-2.157
# Rotatable Bonds:	6
TPSA:	197.74
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.235
Synthetic Accessibility Score:	4.43
Fsp3:	0.591
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:	-6.362
MDCK Permeability:	7.086284313118085e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.847
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	45.59575653076172%
Volume Distribution (VD):	0.552
Pgp-substrate:	25.54237174987793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.698
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.382
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.06
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	1.393
Half-life (T1/2):	0.633

ADMET: Toxicity

hERG Blockers:	0.518
Human Hepatotoxicity (H-HT):	0.125
Drug-inuced Liver Injury (DILI):	0.807
AMES Toxicity:	0.286
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.474
Carcinogencity:	0.334
Eye Corrosion:	0.004
Eye Irritation:	0.043
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC114740

Natural Product ID:	NPC114740
*Common Name:**	Haploperoside
IUPAC Name:	6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-2-one
Synonyms:	Haploperoside
Standard InCHIKey:	FCIZPHNZRNLUJD-HLUXVQISSA-N
Standard InCHI:	InChI=1S/C22H28O13/c1-8-15(24)17(26)19(28)21(32-8)31-7-13-16(25)18(27)20(29)22(35-13)34-12-6-10-9(5-11(12)30-2)3-4-14(23)33-10/h3-6,8,13,15-22,24-29H,7H2,1-2H3/t8-,13+,15-,16+,17+,18-,19+,20+,21+,22+/m0/s1
SMILES:	COc1cc2ccc(=O)oc2cc1O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928410
PubChem CID:	21607625
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0001743] Coumarin 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
NPO1762	Citropsis articulata	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[21985060]
NPO1762	Citropsis articulata	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[21985060]
NPO1762	Citropsis articulata	Species	Rutaceae	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
EC50	2
IC50	2

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	50.0	ug.mL-1	PMID[570863]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	>	100.0	ug.mL-1	PMID[570863]
NPT633	Organism	Leishmania donovani	Leishmania donovani	EC50	>	125.0	ug.mL-1	PMID[570863]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	EC50	>	125.0	ug.mL-1	PMID[570863]

☑ 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 NPC114740 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	411
0.1-0.2	1729
0.2-0.3	3978
0.3-0.4	9115
0.4-0.5	9089
0.5-0.6	4715
0.6-0.7	5418
0.7-0.8	5665
0.8-0.85	1719
0.85-0.9	700
0.9-0.95	150
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC96294
0.9789	High Similarity	NPC52740
0.9655	High Similarity	NPC213197
0.9589	High Similarity	NPC215060
0.9589	High Similarity	NPC476352
0.9517	High Similarity	NPC313334
0.9517	High Similarity	NPC212670
0.9517	High Similarity	NPC206264
0.9463	High Similarity	NPC284810
0.9448	High Similarity	NPC93924
0.9379	High Similarity	NPC41844
0.9379	High Similarity	NPC15577
0.9262	High Similarity	NPC150442
0.9241	High Similarity	NPC476450
0.9231	High Similarity	NPC300611
0.9195	High Similarity	NPC470264
0.9195	High Similarity	NPC176186
0.9195	High Similarity	NPC169404
0.9195	High Similarity	NPC53587
0.9189	High Similarity	NPC21184
0.9189	High Similarity	NPC294522
0.9189	High Similarity	NPC205727
0.9189	High Similarity	NPC120426
0.9184	High Similarity	NPC478237
0.9122	High Similarity	NPC30688
0.9122	High Similarity	NPC176903
0.9116	High Similarity	NPC87950
0.9116	High Similarity	NPC471764
0.9103	High Similarity	NPC138212
0.9091	High Similarity	NPC164148
0.9091	High Similarity	NPC43500
0.9085	High Similarity	NPC103409
0.9054	High Similarity	NPC187398
0.9054	High Similarity	NPC476348
0.9048	High Similarity	NPC199928
0.9048	High Similarity	NPC205361
0.9028	High Similarity	NPC210478
0.8993	High Similarity	NPC106138
0.8986	High Similarity	NPC476347
0.898	High Similarity	NPC85624
0.8966	High Similarity	NPC215512
0.8966	High Similarity	NPC476442
0.8951	High Similarity	NPC104167
0.8951	High Similarity	NPC37468
0.8944	High Similarity	NPC309953
0.894	High Similarity	NPC120774
0.894	High Similarity	NPC163598
0.894	High Similarity	NPC264875
0.8912	High Similarity	NPC292443
0.8912	High Similarity	NPC232228
0.8904	High Similarity	NPC145319
0.8897	High Similarity	NPC202700
0.8889	High Similarity	NPC20796
0.8882	High Similarity	NPC246893
0.8881	High Similarity	NPC470236
0.8873	High Similarity	NPC36437
0.8873	High Similarity	NPC241341
0.8873	High Similarity	NPC233018
0.8859	High Similarity	NPC296377
0.8851	High Similarity	NPC226722
0.8844	High Similarity	NPC478239
0.8844	High Similarity	NPC252169
0.8828	High Similarity	NPC13067
0.8828	High Similarity	NPC100389
0.882	High Similarity	NPC163165
0.8819	High Similarity	NPC164857
0.8803	High Similarity	NPC137669
0.8803	High Similarity	NPC162093
0.88	High Similarity	NPC169510
0.8792	High Similarity	NPC125755
0.8792	High Similarity	NPC476865
0.8784	High Similarity	NPC297342
0.8776	High Similarity	NPC157816
0.8776	High Similarity	NPC475084
0.8759	High Similarity	NPC52086
0.8759	High Similarity	NPC148835
0.8759	High Similarity	NPC20511
0.8759	High Similarity	NPC95162
0.8759	High Similarity	NPC76336
0.8759	High Similarity	NPC139548
0.875	High Similarity	NPC55040
0.875	High Similarity	NPC185778
0.875	High Similarity	NPC240915
0.8741	High Similarity	NPC49074
0.8741	High Similarity	NPC69513
0.8741	High Similarity	NPC215833
0.8733	High Similarity	NPC227902
0.8725	High Similarity	NPC476382
0.8725	High Similarity	NPC34927
0.8725	High Similarity	NPC476869
0.8725	High Similarity	NPC252292
0.8725	High Similarity	NPC277867
0.8725	High Similarity	NPC34587
0.8725	High Similarity	NPC100998
0.8725	High Similarity	NPC476866
0.8725	High Similarity	NPC161700
0.8725	High Similarity	NPC476868
0.8725	High Similarity	NPC476864
0.8707	High Similarity	NPC186406
0.8707	High Similarity	NPC472520
0.8707	High Similarity	NPC279851
0.8701	High Similarity	NPC8712
0.8693	High Similarity	NPC302610
0.869	High Similarity	NPC186418
0.869	High Similarity	NPC126682
0.869	High Similarity	NPC157554
0.869	High Similarity	NPC82271
0.8684	High Similarity	NPC238140
0.8681	High Similarity	NPC7163
0.8681	High Similarity	NPC48863
0.8681	High Similarity	NPC13745
0.8681	High Similarity	NPC251981
0.8675	High Similarity	NPC175976
0.8671	High Similarity	NPC299144
0.8671	High Similarity	NPC319969
0.8662	High Similarity	NPC19242
0.8662	High Similarity	NPC240722
0.8662	High Similarity	NPC244799
0.8658	High Similarity	NPC76176
0.8658	High Similarity	NPC138227
0.8658	High Similarity	NPC168579
0.8658	High Similarity	NPC469313
0.8658	High Similarity	NPC476867
0.865	High Similarity	NPC169645
0.865	High Similarity	NPC84482
0.8649	High Similarity	NPC473873
0.8649	High Similarity	NPC140502
0.8649	High Similarity	NPC473792
0.863	High Similarity	NPC124149
0.8621	High Similarity	NPC73071
0.8618	High Similarity	NPC283839
0.8618	High Similarity	NPC90896
0.8609	High Similarity	NPC473480
0.8609	High Similarity	NPC232992
0.8609	High Similarity	NPC231149
0.8609	High Similarity	NPC15538
0.8608	High Similarity	NPC25389
0.8608	High Similarity	NPC472859
0.8608	High Similarity	NPC311803
0.8601	High Similarity	NPC9912
0.86	High Similarity	NPC469701
0.86	High Similarity	NPC138915
0.86	High Similarity	NPC475096
0.8599	High Similarity	NPC173726
0.8599	High Similarity	NPC241600
0.8592	High Similarity	NPC123127
0.8592	High Similarity	NPC27239
0.8592	High Similarity	NPC295970
0.8591	High Similarity	NPC7439
0.8591	High Similarity	NPC110067
0.8591	High Similarity	NPC37793
0.8591	High Similarity	NPC91492
0.8591	High Similarity	NPC256555
0.8591	High Similarity	NPC34245
0.8571	High Similarity	NPC135345
0.8571	High Similarity	NPC289967
0.8571	High Similarity	NPC226005
0.8571	High Similarity	NPC270256
0.8571	High Similarity	NPC98777
0.8571	High Similarity	NPC212770
0.8571	High Similarity	NPC472611
0.8571	High Similarity	NPC472612
0.8562	High Similarity	NPC286843
0.8562	High Similarity	NPC166180
0.8562	High Similarity	NPC476871
0.8553	High Similarity	NPC48366
0.8552	High Similarity	NPC92830
0.8552	High Similarity	NPC87696
0.8552	High Similarity	NPC474600
0.8544	High Similarity	NPC166277
0.8544	High Similarity	NPC119125
0.8543	High Similarity	NPC190714
0.8543	High Similarity	NPC40222
0.8543	High Similarity	NPC99515
0.8543	High Similarity	NPC268515
0.8533	High Similarity	NPC471763
0.8531	High Similarity	NPC80600
0.8531	High Similarity	NPC472024
0.8528	High Similarity	NPC475155
0.8528	High Similarity	NPC172807
0.8528	High Similarity	NPC254540
0.8528	High Similarity	NPC211594
0.8528	High Similarity	NPC472386
0.8523	High Similarity	NPC469559
0.8523	High Similarity	NPC189115
0.8521	High Similarity	NPC302378
0.8516	High Similarity	NPC78809
0.8514	High Similarity	NPC312881
0.8509	High Similarity	NPC99957
0.8509	High Similarity	NPC181616
0.8503	High Similarity	NPC59324
0.8503	High Similarity	NPC153818
0.8503	High Similarity	NPC232246
0.8503	High Similarity	NPC65530
0.85	High Similarity	NPC121290
0.8497	Intermediate Similarity	NPC94871
0.8497	Intermediate Similarity	NPC306890
0.8497	Intermediate Similarity	NPC476398
0.8497	Intermediate Similarity	NPC259347
0.8497	Intermediate Similarity	NPC470933

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 NPC114740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	943
0.2-0.3	2007
0.3-0.4	2661
0.4-0.5	1829
0.5-0.6	891
0.6-0.7	289
0.7-0.8	128
0.8-0.85	25
0.85-0.9	7
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9517	High Similarity	NPD1653	Approved
0.8322	Intermediate Similarity	NPD7266	Discontinued
0.8313	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD7054	Approved
0.8242	Intermediate Similarity	NPD7472	Approved
0.8133	Intermediate Similarity	NPD7074	Phase 3
0.8095	Intermediate Similarity	NPD7808	Phase 3
0.8092	Intermediate Similarity	NPD1652	Phase 2
0.8084	Intermediate Similarity	NPD6797	Phase 2
0.8036	Intermediate Similarity	NPD7251	Discontinued
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.7964	Intermediate Similarity	NPD5844	Phase 1
0.7963	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1613	Approved
0.7919	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1091	Approved
0.7901	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD5124	Phase 1
0.784	Intermediate Similarity	NPD3817	Phase 2
0.7818	Intermediate Similarity	NPD7199	Phase 2
0.7798	Intermediate Similarity	NPD7228	Approved
0.7742	Intermediate Similarity	NPD6674	Discontinued
0.773	Intermediate Similarity	NPD5402	Approved
0.7718	Intermediate Similarity	NPD3027	Phase 3
0.7716	Intermediate Similarity	NPD37	Approved
0.7683	Intermediate Similarity	NPD4967	Phase 2
0.7683	Intermediate Similarity	NPD4966	Approved
0.7683	Intermediate Similarity	NPD4965	Approved
0.7679	Intermediate Similarity	NPD6166	Phase 2
0.7679	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7549	Discontinued
0.7669	Intermediate Similarity	NPD2801	Approved
0.7655	Intermediate Similarity	NPD422	Phase 1
0.7651	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7240	Approved
0.7616	Intermediate Similarity	NPD6559	Discontinued
0.7607	Intermediate Similarity	NPD1934	Approved
0.759	Intermediate Similarity	NPD6234	Discontinued
0.7584	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD8455	Phase 2
0.7561	Intermediate Similarity	NPD1465	Phase 2
0.7558	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5494	Approved
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.7458	Intermediate Similarity	NPD6841	Approved
0.7458	Intermediate Similarity	NPD6843	Phase 3
0.7458	Intermediate Similarity	NPD6842	Approved
0.7455	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5403	Approved
0.7391	Intermediate Similarity	NPD5401	Approved
0.7378	Intermediate Similarity	NPD4380	Phase 2
0.7351	Intermediate Similarity	NPD3018	Phase 2
0.7349	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3496	Discontinued
0.7346	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7075	Discontinued
0.732	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6190	Approved
0.7303	Intermediate Similarity	NPD4908	Phase 1
0.7297	Intermediate Similarity	NPD3705	Approved
0.7294	Intermediate Similarity	NPD8127	Discontinued
0.729	Intermediate Similarity	NPD447	Suspended
0.729	Intermediate Similarity	NPD1933	Approved
0.7289	Intermediate Similarity	NPD6801	Discontinued
0.7283	Intermediate Similarity	NPD3751	Discontinued
0.7262	Intermediate Similarity	NPD3882	Suspended
0.7251	Intermediate Similarity	NPD3787	Discontinued
0.7247	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7819	Suspended
0.7222	Intermediate Similarity	NPD1511	Approved
0.7222	Intermediate Similarity	NPD6799	Approved
0.7211	Intermediate Similarity	NPD1357	Approved
0.7208	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2982	Phase 2
0.72	Intermediate Similarity	NPD2983	Phase 2
0.7197	Intermediate Similarity	NPD7097	Phase 1
0.7179	Intermediate Similarity	NPD230	Phase 1
0.7161	Intermediate Similarity	NPD6233	Phase 2
0.7152	Intermediate Similarity	NPD3225	Approved
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3750	Approved
0.7135	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD8313	Approved
0.7134	Intermediate Similarity	NPD1512	Approved
0.7133	Intermediate Similarity	NPD2981	Phase 2
0.7127	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7411	Suspended
0.7124	Intermediate Similarity	NPD2861	Phase 2
0.7086	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD919	Approved
0.7067	Intermediate Similarity	NPD1610	Phase 2
0.7052	Intermediate Similarity	NPD6232	Discontinued
0.7048	Intermediate Similarity	NPD3687	Approved
0.7048	Intermediate Similarity	NPD3686	Approved
0.7044	Intermediate Similarity	NPD3748	Approved
0.7037	Intermediate Similarity	NPD4628	Phase 3
0.703	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2424	Discontinued
0.7018	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4060	Phase 1
0.7005	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2796	Approved
0.7	Intermediate Similarity	NPD5353	Approved
0.6987	Remote Similarity	NPD6798	Discontinued
0.6987	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4749	Approved
0.6972	Remote Similarity	NPD290	Approved
0.6972	Remote Similarity	NPD1358	Approved
0.6964	Remote Similarity	NPD6599	Discontinued
0.6962	Remote Similarity	NPD4340	Discontinued
0.6959	Remote Similarity	NPD5536	Phase 2
0.6957	Remote Similarity	NPD5763	Approved
0.6957	Remote Similarity	NPD5762	Approved
0.6951	Remote Similarity	NPD5058	Phase 3
0.6947	Remote Similarity	NPD7680	Approved
0.6936	Remote Similarity	NPD5677	Discontinued
0.6933	Remote Similarity	NPD1778	Approved
0.6932	Remote Similarity	NPD7473	Discontinued
0.6927	Remote Similarity	NPD7583	Approved
0.6914	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1549	Phase 2
0.6909	Remote Similarity	NPD4357	Discontinued
0.6897	Remote Similarity	NPD1247	Approved
0.6894	Remote Similarity	NPD2935	Discontinued
0.6894	Remote Similarity	NPD1551	Phase 2
0.6891	Remote Similarity	NPD7585	Approved
0.6883	Remote Similarity	NPD2797	Approved
0.6879	Remote Similarity	NPD1296	Phase 2
0.6872	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7783	Phase 2
0.6867	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7768	Phase 2
0.6855	Remote Similarity	NPD6355	Discontinued
0.6852	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3540	Phase 1
0.6849	Remote Similarity	NPD7843	Approved
0.6832	Remote Similarity	NPD7033	Discontinued
0.6831	Remote Similarity	NPD9697	Approved
0.6829	Remote Similarity	NPD4110	Phase 3
0.6829	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7157	Approved
0.6824	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6671	Approved
0.6818	Remote Similarity	NPD8651	Approved
0.6815	Remote Similarity	NPD4625	Phase 3
0.6815	Remote Similarity	NPD7095	Approved
0.6813	Remote Similarity	NPD6653	Approved
0.6809	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2684	Approved
0.6805	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6959	Discontinued
0.6792	Remote Similarity	NPD4140	Approved
0.679	Remote Similarity	NPD3539	Phase 1
0.6783	Remote Similarity	NPD3134	Approved
0.6781	Remote Similarity	NPD228	Approved
0.678	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3268	Approved
0.6771	Remote Similarity	NPD7435	Discontinued
0.677	Remote Similarity	NPD4536	Approved
0.677	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4538	Approved
0.6769	Remote Similarity	NPD8151	Discontinued
0.6768	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4678	Approved
0.6765	Remote Similarity	NPD4675	Approved
0.6755	Remote Similarity	NPD5691	Approved
0.6752	Remote Similarity	NPD6832	Phase 2
0.675	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1375	Discontinued
0.674	Remote Similarity	NPD7038	Approved
0.674	Remote Similarity	NPD7039	Approved
0.6735	Remote Similarity	NPD5535	Approved
0.6728	Remote Similarity	NPD1510	Phase 2
0.6727	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4626	Approved
0.6707	Remote Similarity	NPD1774	Approved
0.6707	Remote Similarity	NPD5297	Approved
0.6707	Remote Similarity	NPD7212	Phase 2
0.6707	Remote Similarity	NPD7213	Phase 3
0.6706	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2415	Discontinued
0.6702	Remote Similarity	NPD6777	Approved
0.6702	Remote Similarity	NPD6781	Approved
0.6702	Remote Similarity	NPD6782	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