NPASS Compound

Structure

NPC471044 OpenBabel07101718232D 28 31 0 0 1 0 0 0 0 0999 V2000 -0.4258 -3.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 -1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4190 2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 -0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 -1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 -1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0871 -2.8138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.6182 0.3693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2579 -0.7014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0108 -0.7200 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8868 -1.0520 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2471 0.0187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0869 -2.8288 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8477 -1.2329 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 2.2382 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3999 -1.9404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 4 27 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 18 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 12 27 1 0 0 0 0 13 21 1 0 0 0 0 13 28 1 0 0 0 0 14 24 2 0 0 0 0 14 28 1 0 0 0 0 15 6 1 1 0 0 0 15 16 1 0 0 0 0 16 20 1 0 0 0 0 17 22 1 6 0 0 0 17 23 1 0 0 0 0 18 21 1 6 0 0 0 18 22 1 0 0 0 0 19 23 1 6 0 0 0 19 25 1 0 0 0 0 20 23 1 0 0 0 0 20 26 2 0 0 0 0 21 2 1 6 0 0 0 22 3 1 6 0 0 0 23 11 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.26
Volume:	410.817
LogP:	2.528
LogD:	2.621
LogS:	-4.108
# Rotatable Bonds:	5
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.743
Synthetic Accessibility Score:	5.945
Fsp3:	0.913
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.746
MDCK Permeability:	3.082022521994077e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.84
30% Bioavailability (F30%):	0.875

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.837
Plasma Protein Binding (PPB):	55.903526306152344%
Volume Distribution (VD):	0.912
Pgp-substrate:	47.79522705078125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.516
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.771
CYP3A4-substrate:	0.465

ADMET: Excretion

Clearance (CL):	4.729
Half-life (T1/2):	0.65

ADMET: Toxicity

hERG Blockers:	0.307
Human Hepatotoxicity (H-HT):	0.371
Drug-inuced Liver Injury (DILI):	0.141
AMES Toxicity:	0.112
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.632
Carcinogencity:	0.527
Eye Corrosion:	0.596
Eye Irritation:	0.535
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC471044

Natural Product ID:	NPC471044
*Common Name:**	Crotonkinin G
IUPAC Name:	n.a.
Synonyms:	crotonkinin G
Standard InCHIKey:	GDGOVQAHSVMHTH-GMLUZKLCSA-N
Standard InCHI:	InChI=1S/C23H36O5/c1-14(24)28-13-21(2)8-5-9-22(3)17-7-6-15-11-23(17,19(25)10-18(21)22)20(26)16(15)12-27-4/h15-19,25H,5-13H2,1-4H3/t15-,16?,17+,18-,19-,21-,22+,23-/m1/s1
SMILES:	COCC1[C@@H]2CC[C@@H]3[C@](C1=O)(C2)[C@H](O)C[C@H]1[C@@]3(C)CCC[C@]1(C)COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337583
PubChem CID:	71578805
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510600]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18161942]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[19899773]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22085418]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22085418]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22197145]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	whole plants	Vietnam	2009-Aug	PMID[23347584]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	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
Others	1

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	11.14	%	PMID[534807]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4290.0	nM	PMID[534807]

☑ 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 NPC471044 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	367
0.1-0.2	2862
0.2-0.3	8239
0.3-0.4	14378
0.4-0.5	6038
0.5-0.6	4771
0.6-0.7	4532
0.7-0.8	1216
0.8-0.85	208
0.85-0.9	68
0.9-0.95	16
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473336
0.9359	High Similarity	NPC201276
0.9359	High Similarity	NPC80891
0.9231	High Similarity	NPC80089
0.9231	High Similarity	NPC224802
0.9231	High Similarity	NPC34046
0.9231	High Similarity	NPC324700
0.9231	High Similarity	NPC171426
0.907	High Similarity	NPC476189
0.9024	High Similarity	NPC219535
0.9024	High Similarity	NPC319909
0.9024	High Similarity	NPC237938
0.9012	High Similarity	NPC289486
0.9012	High Similarity	NPC61107
0.8974	High Similarity	NPC4209
0.8916	High Similarity	NPC473350
0.8875	High Similarity	NPC320144
0.8864	High Similarity	NPC62407
0.8864	High Similarity	NPC287354
0.8861	High Similarity	NPC207010
0.8861	High Similarity	NPC477918
0.8861	High Similarity	NPC317913
0.8846	High Similarity	NPC212733
0.881	High Similarity	NPC302111
0.881	High Similarity	NPC83242
0.8795	High Similarity	NPC477434
0.878	High Similarity	NPC121121
0.8765	High Similarity	NPC261616
0.875	High Similarity	NPC47853
0.875	High Similarity	NPC185465
0.8736	High Similarity	NPC52756
0.8734	High Similarity	NPC477933
0.8734	High Similarity	NPC477932
0.8721	High Similarity	NPC61688
0.8721	High Similarity	NPC471459
0.8721	High Similarity	NPC200580
0.8721	High Similarity	NPC67653
0.8718	High Similarity	NPC280026
0.8718	High Similarity	NPC167702
0.8659	High Similarity	NPC58631
0.8625	High Similarity	NPC471151
0.8625	High Similarity	NPC143133
0.8625	High Similarity	NPC298168
0.8621	High Similarity	NPC77756
0.8608	High Similarity	NPC477934
0.8605	High Similarity	NPC131104
0.8605	High Similarity	NPC3032
0.8605	High Similarity	NPC473319
0.859	High Similarity	NPC232112
0.8571	High Similarity	NPC50438
0.8571	High Similarity	NPC473299
0.8556	High Similarity	NPC116683
0.8556	High Similarity	NPC329910
0.8554	High Similarity	NPC30583
0.8537	High Similarity	NPC477851
0.8506	High Similarity	NPC56962
0.8506	High Similarity	NPC24705
0.8488	Intermediate Similarity	NPC252714
0.8481	Intermediate Similarity	NPC477930
0.8462	Intermediate Similarity	NPC58057
0.8462	Intermediate Similarity	NPC320549
0.8462	Intermediate Similarity	NPC156277
0.8462	Intermediate Similarity	NPC253586
0.8462	Intermediate Similarity	NPC469940
0.8462	Intermediate Similarity	NPC151018
0.8452	Intermediate Similarity	NPC292458
0.8452	Intermediate Similarity	NPC217559
0.8452	Intermediate Similarity	NPC268578
0.8444	Intermediate Similarity	NPC470229
0.8444	Intermediate Similarity	NPC470232
0.8434	Intermediate Similarity	NPC12933
0.8434	Intermediate Similarity	NPC73515
0.8434	Intermediate Similarity	NPC469745
0.8415	Intermediate Similarity	NPC476176
0.8415	Intermediate Similarity	NPC220379
0.8409	Intermediate Similarity	NPC475211
0.8409	Intermediate Similarity	NPC88337
0.8395	Intermediate Similarity	NPC212453
0.8391	Intermediate Similarity	NPC226491
0.8391	Intermediate Similarity	NPC477614
0.8375	Intermediate Similarity	NPC97534
0.8375	Intermediate Similarity	NPC159789
0.8375	Intermediate Similarity	NPC174964
0.8375	Intermediate Similarity	NPC195155
0.8375	Intermediate Similarity	NPC273366
0.8372	Intermediate Similarity	NPC472272
0.8372	Intermediate Similarity	NPC80700
0.837	Intermediate Similarity	NPC78427
0.837	Intermediate Similarity	NPC16911
0.837	Intermediate Similarity	NPC471038
0.8352	Intermediate Similarity	NPC193785
0.8333	Intermediate Similarity	NPC13494
0.8333	Intermediate Similarity	NPC475118
0.8333	Intermediate Similarity	NPC470386
0.8333	Intermediate Similarity	NPC477929
0.8333	Intermediate Similarity	NPC477935
0.8333	Intermediate Similarity	NPC470385
0.8313	Intermediate Similarity	NPC470609
0.8295	Intermediate Similarity	NPC477443
0.8295	Intermediate Similarity	NPC477440
0.8295	Intermediate Similarity	NPC471043
0.8293	Intermediate Similarity	NPC471045
0.8293	Intermediate Similarity	NPC329117
0.828	Intermediate Similarity	NPC108371
0.828	Intermediate Similarity	NPC94906
0.828	Intermediate Similarity	NPC287676
0.8276	Intermediate Similarity	NPC263802
0.8276	Intermediate Similarity	NPC239938
0.8272	Intermediate Similarity	NPC475742
0.8272	Intermediate Similarity	NPC472487
0.8272	Intermediate Similarity	NPC474020
0.8272	Intermediate Similarity	NPC471046
0.8272	Intermediate Similarity	NPC472486
0.8272	Intermediate Similarity	NPC5767
0.8256	Intermediate Similarity	NPC477445
0.8256	Intermediate Similarity	NPC477205
0.825	Intermediate Similarity	NPC254340
0.8228	Intermediate Similarity	NPC89310
0.8222	Intermediate Similarity	NPC473690
0.8222	Intermediate Similarity	NPC287118
0.8222	Intermediate Similarity	NPC471902
0.8205	Intermediate Similarity	NPC476734
0.8205	Intermediate Similarity	NPC131892
0.8205	Intermediate Similarity	NPC469941
0.8205	Intermediate Similarity	NPC252032
0.8205	Intermediate Similarity	NPC213178
0.8205	Intermediate Similarity	NPC319671
0.8205	Intermediate Similarity	NPC6120
0.8205	Intermediate Similarity	NPC327728
0.8202	Intermediate Similarity	NPC477444
0.8202	Intermediate Similarity	NPC477442
0.8202	Intermediate Similarity	NPC477433
0.8191	Intermediate Similarity	NPC163963
0.8191	Intermediate Similarity	NPC75941
0.8191	Intermediate Similarity	NPC52899
0.8191	Intermediate Similarity	NPC289148
0.8191	Intermediate Similarity	NPC46848
0.8182	Intermediate Similarity	NPC471221
0.8172	Intermediate Similarity	NPC474793
0.8172	Intermediate Similarity	NPC472028
0.8171	Intermediate Similarity	NPC475031
0.8171	Intermediate Similarity	NPC221420
0.8171	Intermediate Similarity	NPC23884
0.8161	Intermediate Similarity	NPC114378
0.8161	Intermediate Similarity	NPC103782
0.8152	Intermediate Similarity	NPC470387
0.8152	Intermediate Similarity	NPC29410
0.8152	Intermediate Similarity	NPC200054
0.8148	Intermediate Similarity	NPC125767
0.8148	Intermediate Similarity	NPC472311
0.8148	Intermediate Similarity	NPC21220
0.8148	Intermediate Similarity	NPC186851
0.814	Intermediate Similarity	NPC181871
0.814	Intermediate Similarity	NPC9060
0.8132	Intermediate Similarity	NPC470424
0.8118	Intermediate Similarity	NPC100366
0.8118	Intermediate Similarity	NPC154043
0.8118	Intermediate Similarity	NPC268040
0.8118	Intermediate Similarity	NPC242771
0.8118	Intermediate Similarity	NPC202688
0.8118	Intermediate Similarity	NPC60018
0.8118	Intermediate Similarity	NPC311642
0.8118	Intermediate Similarity	NPC477936
0.8118	Intermediate Similarity	NPC164289
0.8111	Intermediate Similarity	NPC470230
0.8111	Intermediate Similarity	NPC475416
0.8111	Intermediate Similarity	NPC198242
0.8111	Intermediate Similarity	NPC471901
0.8111	Intermediate Similarity	NPC211403
0.8105	Intermediate Similarity	NPC246736
0.8105	Intermediate Similarity	NPC124544
0.8105	Intermediate Similarity	NPC214946
0.8105	Intermediate Similarity	NPC286519
0.8105	Intermediate Similarity	NPC470172
0.8105	Intermediate Similarity	NPC275990
0.8105	Intermediate Similarity	NPC88203
0.8105	Intermediate Similarity	NPC76866
0.8105	Intermediate Similarity	NPC304832
0.8105	Intermediate Similarity	NPC148628
0.8095	Intermediate Similarity	NPC472853
0.809	Intermediate Similarity	NPC213832
0.809	Intermediate Similarity	NPC57954
0.8085	Intermediate Similarity	NPC41971
0.8085	Intermediate Similarity	NPC37047
0.8085	Intermediate Similarity	NPC180733
0.8072	Intermediate Similarity	NPC476732
0.8072	Intermediate Similarity	NPC243594
0.8072	Intermediate Similarity	NPC199965
0.8072	Intermediate Similarity	NPC31031
0.8068	Intermediate Similarity	NPC202937
0.8068	Intermediate Similarity	NPC33768
0.8068	Intermediate Similarity	NPC470920
0.8065	Intermediate Similarity	NPC472273
0.8046	Intermediate Similarity	NPC131350
0.8046	Intermediate Similarity	NPC62572
0.8046	Intermediate Similarity	NPC266651
0.8046	Intermediate Similarity	NPC474572
0.8043	Intermediate Similarity	NPC263135
0.8043	Intermediate Similarity	NPC305808
0.8043	Intermediate Similarity	NPC279974

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 NPC471044 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	3219
0.2-0.3	3561
0.3-0.4	1220
0.4-0.5	324
0.5-0.6	232
0.6-0.7	166
0.7-0.8	22
0.8-0.85	6
0.85-0.9	5
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD6118	Approved
0.9231	High Similarity	NPD6697	Approved
0.9231	High Similarity	NPD6115	Approved
0.9231	High Similarity	NPD6114	Approved
0.8974	High Similarity	NPD6117	Approved
0.8861	High Similarity	NPD6116	Phase 1
0.8718	High Similarity	NPD6113	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD3703	Phase 2
0.8205	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5777	Approved
0.8	Intermediate Similarity	NPD6081	Approved
0.7875	Intermediate Similarity	NPD4789	Approved
0.7875	Intermediate Similarity	NPD4244	Approved
0.7875	Intermediate Similarity	NPD4245	Approved
0.7848	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5360	Phase 3
0.7841	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD4224	Phase 2
0.775	Intermediate Similarity	NPD3698	Phase 2
0.7717	Intermediate Similarity	NPD8035	Phase 2
0.7717	Intermediate Similarity	NPD8034	Phase 2
0.7711	Intermediate Similarity	NPD3702	Approved
0.7692	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3671	Phase 1
0.7423	Intermediate Similarity	NPD7638	Approved
0.7349	Intermediate Similarity	NPD4758	Discontinued
0.7347	Intermediate Similarity	NPD7640	Approved
0.7347	Intermediate Similarity	NPD7639	Approved
0.7347	Intermediate Similarity	NPD8418	Phase 2
0.7317	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6928	Phase 2
0.7263	Intermediate Similarity	NPD6399	Phase 3
0.7241	Intermediate Similarity	NPD5364	Discontinued
0.7228	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7632	Discontinued
0.7045	Intermediate Similarity	NPD4802	Phase 2
0.7045	Intermediate Similarity	NPD4238	Approved
0.7019	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7748	Approved
0.699	Remote Similarity	NPD7128	Approved
0.699	Remote Similarity	NPD6402	Approved
0.699	Remote Similarity	NPD6675	Approved
0.699	Remote Similarity	NPD5739	Approved
0.6979	Remote Similarity	NPD7515	Phase 2
0.6957	Remote Similarity	NPD4786	Approved
0.6947	Remote Similarity	NPD5328	Approved
0.6931	Remote Similarity	NPD1700	Approved
0.6857	Remote Similarity	NPD6881	Approved
0.6857	Remote Similarity	NPD6899	Approved
0.6857	Remote Similarity	NPD7320	Approved
0.6848	Remote Similarity	NPD4788	Approved
0.6824	Remote Similarity	NPD4787	Phase 1
0.6809	Remote Similarity	NPD3618	Phase 1
0.6804	Remote Similarity	NPD6079	Approved
0.68	Remote Similarity	NPD7902	Approved
0.68	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD6084	Phase 2
0.6792	Remote Similarity	NPD6373	Approved
0.6792	Remote Similarity	NPD6372	Approved
0.6786	Remote Similarity	NPD6319	Approved
0.6762	Remote Similarity	NPD5697	Approved
0.6762	Remote Similarity	NPD5701	Approved
0.6739	Remote Similarity	NPD3667	Approved
0.6729	Remote Similarity	NPD7290	Approved
0.6729	Remote Similarity	NPD6883	Approved
0.6729	Remote Similarity	NPD7102	Approved
0.6727	Remote Similarity	NPD6940	Discontinued
0.6698	Remote Similarity	NPD6011	Approved
0.6697	Remote Similarity	NPD4632	Approved
0.6697	Remote Similarity	NPD8133	Approved
0.6696	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6638	Remote Similarity	NPD6616	Approved
0.6637	Remote Similarity	NPD6059	Approved
0.6637	Remote Similarity	NPD6054	Approved
0.6636	Remote Similarity	NPD6012	Approved
0.6636	Remote Similarity	NPD6013	Approved
0.6636	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6014	Approved
0.6632	Remote Similarity	NPD5330	Approved
0.6632	Remote Similarity	NPD7521	Approved
0.6632	Remote Similarity	NPD7334	Approved
0.6632	Remote Similarity	NPD7146	Approved
0.6632	Remote Similarity	NPD6409	Approved
0.6632	Remote Similarity	NPD6684	Approved
0.6625	Remote Similarity	NPD3198	Approved
0.6606	Remote Similarity	NPD6882	Approved
0.6606	Remote Similarity	NPD8297	Approved
0.6581	Remote Similarity	NPD7078	Approved
0.6581	Remote Similarity	NPD8293	Discontinued
0.6566	Remote Similarity	NPD4202	Approved
0.6566	Remote Similarity	NPD8171	Discontinued
0.6535	Remote Similarity	NPD4697	Phase 3
0.6535	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5222	Approved
0.6535	Remote Similarity	NPD5221	Approved
0.6522	Remote Similarity	NPD7525	Registered
0.6522	Remote Similarity	NPD6370	Approved
0.6518	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6009	Approved
0.6509	Remote Similarity	NPD6920	Discontinued
0.65	Remote Similarity	NPD7900	Approved
0.65	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6903	Approved
0.6481	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4755	Approved
0.6471	Remote Similarity	NPD5173	Approved
0.6471	Remote Similarity	NPD7319	Approved
0.6466	Remote Similarity	NPD7604	Phase 2
0.6465	Remote Similarity	NPD7637	Suspended
0.6458	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6412	Phase 2
0.6436	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5695	Phase 3
0.6435	Remote Similarity	NPD6015	Approved
0.6435	Remote Similarity	NPD5983	Phase 2
0.6435	Remote Similarity	NPD6016	Approved
0.6429	Remote Similarity	NPD6868	Approved
0.6422	Remote Similarity	NPD4634	Approved
0.6421	Remote Similarity	NPD3666	Approved
0.6421	Remote Similarity	NPD3133	Approved
0.6421	Remote Similarity	NPD3665	Phase 1
0.641	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5696	Approved
0.6396	Remote Similarity	NPD8298	Phase 2
0.6379	Remote Similarity	NPD5988	Approved
0.6356	Remote Similarity	NPD7507	Approved
0.6356	Remote Similarity	NPD6336	Discontinued
0.6346	Remote Similarity	NPD5285	Approved
0.6346	Remote Similarity	NPD5286	Approved
0.6346	Remote Similarity	NPD4696	Approved
0.6346	Remote Similarity	NPD4700	Approved
0.6325	Remote Similarity	NPD8328	Phase 3
0.6316	Remote Similarity	NPD6335	Approved
0.6316	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD3669	Approved
0.63	Remote Similarity	NPD6411	Approved
0.6293	Remote Similarity	NPD6921	Approved
0.6289	Remote Similarity	NPD6098	Approved
0.6286	Remote Similarity	NPD5223	Approved
0.6283	Remote Similarity	NPD6274	Approved
0.6277	Remote Similarity	NPD1780	Approved
0.6277	Remote Similarity	NPD1779	Approved
0.6275	Remote Similarity	NPD7991	Discontinued
0.6273	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD4753	Phase 2
0.6263	Remote Similarity	NPD6673	Approved
0.6263	Remote Similarity	NPD6080	Approved
0.6263	Remote Similarity	NPD6904	Approved
0.6261	Remote Similarity	NPD7101	Approved
0.6261	Remote Similarity	NPD7100	Approved
0.625	Remote Similarity	NPD6033	Approved
0.625	Remote Similarity	NPD3668	Phase 3
0.6239	Remote Similarity	NPD6415	Discontinued
0.6228	Remote Similarity	NPD6317	Approved
0.6226	Remote Similarity	NPD5226	Approved
0.6226	Remote Similarity	NPD5211	Phase 2
0.6226	Remote Similarity	NPD5225	Approved
0.6226	Remote Similarity	NPD5224	Approved
0.6226	Remote Similarity	NPD4633	Approved
0.6207	Remote Similarity	NPD229	Approved
0.62	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6700	Approved
0.6174	Remote Similarity	NPD6313	Approved
0.6174	Remote Similarity	NPD6314	Approved
0.6168	Remote Similarity	NPD5175	Approved
0.6168	Remote Similarity	NPD4754	Approved
0.6168	Remote Similarity	NPD5174	Approved
0.6154	Remote Similarity	NPD6909	Approved
0.6154	Remote Similarity	NPD6908	Approved
0.6139	Remote Similarity	NPD6703	Approved
0.6139	Remote Similarity	NPD6702	Approved
0.6129	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3617	Approved
0.6122	Remote Similarity	NPD8308	Discontinued
0.6122	Remote Similarity	NPD5279	Phase 3
0.6118	Remote Similarity	NPD7909	Approved
0.6111	Remote Similarity	NPD5141	Approved
0.6105	Remote Similarity	NPD5369	Approved
0.61	Remote Similarity	NPD6101	Approved
0.61	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4225	Approved
0.6091	Remote Similarity	NPD6686	Approved
0.6078	Remote Similarity	NPD5779	Approved
0.6078	Remote Similarity	NPD5778	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