NPASS Compound

Structure

NPC471040 OpenBabel07101719512D 27 30 0 0 1 0 0 0 0 0999 V2000 0.8510 -3.7991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 -1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3709 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8709 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2650 -1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9195 0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0896 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4576 -2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0735 -2.8242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5775 -0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0646 -1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5630 -1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2472 -0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.0801 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8709 -1.0801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4504 -2.2574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0291 -2.5294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3709 -0.2141 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3709 -1.9462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3405 -2.1440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 4 6 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 5 17 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 22 1 0 0 0 0 11 15 2 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 12 23 2 0 0 0 0 13 24 2 0 0 0 0 13 27 1 0 0 0 0 14 9 1 1 0 0 0 14 15 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 6 0 0 0 17 20 1 1 0 0 0 17 21 1 0 0 0 0 18 20 1 1 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 25 2 0 0 0 0 19 26 1 0 0 0 0 20 2 1 1 0 0 0 21 3 1 1 0 0 0 22 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.21
Volume:	388.248
LogP:	2.939
LogD:	2.201
LogS:	-3.36
# Rotatable Bonds:	4
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.601
Synthetic Accessibility Score:	5.973
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.634
MDCK Permeability:	4.944803367834538e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.961
Human Intestinal Absorption (HIA):	0.182
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.917

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.895
Plasma Protein Binding (PPB):	50.205116271972656%
Volume Distribution (VD):	0.347
Pgp-substrate:	44.29755401611328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.445
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.258
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.075
CYP3A4-inhibitor:	0.591
CYP3A4-substrate:	0.252

ADMET: Excretion

Clearance (CL):	1.31
Half-life (T1/2):	0.488

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.574
Drug-inuced Liver Injury (DILI):	0.077
AMES Toxicity:	0.832
Rat Oral Acute Toxicity:	0.786
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.953
Carcinogencity:	0.839
Eye Corrosion:	0.967
Eye Irritation:	0.696
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC471040

Natural Product ID:	NPC471040
*Common Name:**	Crotonkinin C
IUPAC Name:	n.a.
Synonyms:	crotonkinin C
Standard InCHIKey:	UKKLQQNAXRBSIP-JKYGVMPDSA-N
Standard InCHI:	InChI=1S/C22H30O5/c1-13(24)27-16-9-14-10-22(11-15(14)12-23)8-5-17-20(2,18(16)22)6-4-7-21(17,3)19(25)26/h11-12,14,16-18H,4-10H2,1-3H3,(H,25,26)/t14-,16+,17+,18+,20-,21+,22+/m1/s1
SMILES:	CC(=O)OC1CC2CC3(C1C4(CCCC(C4CC3)(C)C(=O)O)C)C=C2C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337579
PubChem CID:	71578722
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	=	41.75	%	PMID[570438]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4960.0	nM	PMID[570438]

☑ 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 NPC471040 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	192
0.1-0.2	1180
0.2-0.3	4823
0.3-0.4	11029
0.4-0.5	10909
0.5-0.6	6672
0.6-0.7	5359
0.7-0.8	2333
0.8-0.85	179
0.85-0.9	16
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC471039
0.9043	High Similarity	NPC471041
0.9011	High Similarity	NPC474185
0.8791	High Similarity	NPC328141
0.8737	High Similarity	NPC194196
0.8736	High Similarity	NPC142683
0.871	High Similarity	NPC269729
0.8617	High Similarity	NPC274417
0.8602	High Similarity	NPC79117
0.8571	High Similarity	NPC282233
0.8571	High Similarity	NPC95585
0.8454	Intermediate Similarity	NPC117685
0.8454	Intermediate Similarity	NPC35751
0.8438	Intermediate Similarity	NPC473456
0.8421	Intermediate Similarity	NPC139459
0.8409	Intermediate Similarity	NPC90055
0.8387	Intermediate Similarity	NPC471896
0.8384	Intermediate Similarity	NPC264048
0.837	Intermediate Similarity	NPC473229
0.837	Intermediate Similarity	NPC474925
0.8351	Intermediate Similarity	NPC114274
0.8351	Intermediate Similarity	NPC471966
0.8333	Intermediate Similarity	NPC248758
0.8316	Intermediate Similarity	NPC272635
0.8316	Intermediate Similarity	NPC159410
0.8316	Intermediate Similarity	NPC74751
0.8316	Intermediate Similarity	NPC169751
0.8298	Intermediate Similarity	NPC230064
0.8298	Intermediate Similarity	NPC250753
0.8276	Intermediate Similarity	NPC59436
0.8265	Intermediate Similarity	NPC475392
0.8265	Intermediate Similarity	NPC471413
0.8265	Intermediate Similarity	NPC475202
0.8265	Intermediate Similarity	NPC475385
0.8265	Intermediate Similarity	NPC201406
0.8247	Intermediate Similarity	NPC292133
0.8229	Intermediate Similarity	NPC470016
0.8229	Intermediate Similarity	NPC279974
0.8229	Intermediate Similarity	NPC139570
0.8229	Intermediate Similarity	NPC317586
0.8222	Intermediate Similarity	NPC471037
0.8211	Intermediate Similarity	NPC107674
0.8211	Intermediate Similarity	NPC214756
0.8211	Intermediate Similarity	NPC272075
0.8211	Intermediate Similarity	NPC139692
0.8211	Intermediate Similarity	NPC295643
0.8211	Intermediate Similarity	NPC151722
0.8211	Intermediate Similarity	NPC170220
0.8211	Intermediate Similarity	NPC472871
0.8211	Intermediate Similarity	NPC294263
0.8211	Intermediate Similarity	NPC141497
0.82	Intermediate Similarity	NPC180204
0.82	Intermediate Similarity	NPC112009
0.82	Intermediate Similarity	NPC176883
0.8191	Intermediate Similarity	NPC85173
0.8191	Intermediate Similarity	NPC113989
0.8191	Intermediate Similarity	NPC120840
0.8191	Intermediate Similarity	NPC148414
0.8191	Intermediate Similarity	NPC475965
0.8191	Intermediate Similarity	NPC175628
0.8191	Intermediate Similarity	NPC111585
0.8191	Intermediate Similarity	NPC474728
0.8191	Intermediate Similarity	NPC474842
0.8191	Intermediate Similarity	NPC126993
0.8182	Intermediate Similarity	NPC118174
0.8182	Intermediate Similarity	NPC471412
0.8182	Intermediate Similarity	NPC81530
0.8182	Intermediate Similarity	NPC469327
0.8172	Intermediate Similarity	NPC474677
0.8172	Intermediate Similarity	NPC472870
0.8172	Intermediate Similarity	NPC206060
0.8172	Intermediate Similarity	NPC328539
0.8152	Intermediate Similarity	NPC73038
0.8152	Intermediate Similarity	NPC325594
0.8152	Intermediate Similarity	NPC471042
0.8144	Intermediate Similarity	NPC151725
0.8144	Intermediate Similarity	NPC192428
0.8144	Intermediate Similarity	NPC106425
0.8144	Intermediate Similarity	NPC122324
0.8144	Intermediate Similarity	NPC5532
0.8144	Intermediate Similarity	NPC29952
0.8144	Intermediate Similarity	NPC327788
0.8144	Intermediate Similarity	NPC469545
0.8144	Intermediate Similarity	NPC219353
0.8144	Intermediate Similarity	NPC61369
0.8137	Intermediate Similarity	NPC44063
0.8132	Intermediate Similarity	NPC470812
0.8125	Intermediate Similarity	NPC475118
0.8125	Intermediate Similarity	NPC471207
0.8125	Intermediate Similarity	NPC240617
0.8125	Intermediate Similarity	NPC166906
0.8111	Intermediate Similarity	NPC470813
0.8105	Intermediate Similarity	NPC60755
0.8105	Intermediate Similarity	NPC185936
0.8105	Intermediate Similarity	NPC470590
0.8105	Intermediate Similarity	NPC145067
0.8105	Intermediate Similarity	NPC233455
0.8105	Intermediate Similarity	NPC476187
0.8105	Intermediate Similarity	NPC285184
0.8105	Intermediate Similarity	NPC86266
0.8105	Intermediate Similarity	NPC77099
0.8105	Intermediate Similarity	NPC212301
0.8105	Intermediate Similarity	NPC110657
0.8105	Intermediate Similarity	NPC218301
0.8105	Intermediate Similarity	NPC65120
0.8105	Intermediate Similarity	NPC158030
0.8105	Intermediate Similarity	NPC168027
0.8105	Intermediate Similarity	NPC26888
0.8105	Intermediate Similarity	NPC4036
0.81	Intermediate Similarity	NPC473163
0.81	Intermediate Similarity	NPC162973
0.81	Intermediate Similarity	NPC136289
0.8085	Intermediate Similarity	NPC469546
0.8085	Intermediate Similarity	NPC30522
0.8085	Intermediate Similarity	NPC119416
0.8085	Intermediate Similarity	NPC474704
0.8085	Intermediate Similarity	NPC475921
0.8085	Intermediate Similarity	NPC474889
0.8081	Intermediate Similarity	NPC476274
0.8077	Intermediate Similarity	NPC239097
0.8065	Intermediate Similarity	NPC142361
0.8065	Intermediate Similarity	NPC474684
0.8061	Intermediate Similarity	NPC108078
0.8061	Intermediate Similarity	NPC476768
0.8061	Intermediate Similarity	NPC253826
0.8061	Intermediate Similarity	NPC474343
0.8061	Intermediate Similarity	NPC26413
0.8061	Intermediate Similarity	NPC226986
0.8058	Intermediate Similarity	NPC469844
0.8058	Intermediate Similarity	NPC189075
0.8058	Intermediate Similarity	NPC275539
0.8043	Intermediate Similarity	NPC2709
0.8043	Intermediate Similarity	NPC474971
0.8043	Intermediate Similarity	NPC323765
0.8043	Intermediate Similarity	NPC65661
0.8041	Intermediate Similarity	NPC470232
0.8041	Intermediate Similarity	NPC473170
0.8041	Intermediate Similarity	NPC476174
0.8041	Intermediate Similarity	NPC470229
0.8041	Intermediate Similarity	NPC98639
0.8037	Intermediate Similarity	NPC298278
0.8022	Intermediate Similarity	NPC215893
0.8021	Intermediate Similarity	NPC86368
0.8021	Intermediate Similarity	NPC474436
0.8021	Intermediate Similarity	NPC63118
0.8021	Intermediate Similarity	NPC477855
0.8021	Intermediate Similarity	NPC470224
0.8021	Intermediate Similarity	NPC38232
0.8021	Intermediate Similarity	NPC298554
0.8021	Intermediate Similarity	NPC49776
0.8021	Intermediate Similarity	NPC472303
0.802	Intermediate Similarity	NPC179208
0.802	Intermediate Similarity	NPC312900
0.8019	Intermediate Similarity	NPC73050
0.8	Intermediate Similarity	NPC183283
0.8	Intermediate Similarity	NPC8062
0.8	Intermediate Similarity	NPC224720
0.8	Intermediate Similarity	NPC472866
0.8	Intermediate Similarity	NPC476223
0.8	Intermediate Similarity	NPC310981
0.8	Intermediate Similarity	NPC476240
0.8	Intermediate Similarity	NPC278459
0.8	Intermediate Similarity	NPC191684
0.7981	Intermediate Similarity	NPC41405
0.7981	Intermediate Similarity	NPC2766
0.798	Intermediate Similarity	NPC108368
0.798	Intermediate Similarity	NPC58942
0.798	Intermediate Similarity	NPC26270
0.798	Intermediate Similarity	NPC471717
0.798	Intermediate Similarity	NPC260149
0.798	Intermediate Similarity	NPC57079
0.798	Intermediate Similarity	NPC119036
0.798	Intermediate Similarity	NPC98868
0.798	Intermediate Similarity	NPC478056
0.7979	Intermediate Similarity	NPC80335
0.7979	Intermediate Similarity	NPC4309
0.7979	Intermediate Similarity	NPC246708
0.7979	Intermediate Similarity	NPC182797
0.7979	Intermediate Similarity	NPC224145
0.7979	Intermediate Similarity	NPC104560
0.7979	Intermediate Similarity	NPC52169
0.7979	Intermediate Similarity	NPC40552
0.7961	Intermediate Similarity	NPC220974
0.7961	Intermediate Similarity	NPC110496
0.7961	Intermediate Similarity	NPC475294
0.7959	Intermediate Similarity	NPC471153
0.7959	Intermediate Similarity	NPC134072
0.7959	Intermediate Similarity	NPC200054
0.7959	Intermediate Similarity	NPC301534
0.7959	Intermediate Similarity	NPC328371
0.7959	Intermediate Similarity	NPC58052
0.7959	Intermediate Similarity	NPC250757
0.7959	Intermediate Similarity	NPC305483
0.7959	Intermediate Similarity	NPC471822
0.7959	Intermediate Similarity	NPC328162
0.7959	Intermediate Similarity	NPC104568
0.7959	Intermediate Similarity	NPC329910
0.7959	Intermediate Similarity	NPC29410
0.7959	Intermediate Similarity	NPC234993
0.7959	Intermediate Similarity	NPC111684

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 NPC471040 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1518
0.2-0.3	3789
0.3-0.4	2414
0.4-0.5	777
0.5-0.6	214
0.6-0.7	159
0.7-0.8	106
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8316	Intermediate Similarity	NPD7748	Approved
0.8144	Intermediate Similarity	NPD4697	Phase 3
0.8137	Intermediate Similarity	NPD5697	Approved
0.8105	Intermediate Similarity	NPD7515	Phase 2
0.8105	Intermediate Similarity	NPD6079	Approved
0.8085	Intermediate Similarity	NPD5328	Approved
0.8061	Intermediate Similarity	NPD7902	Approved
0.8058	Intermediate Similarity	NPD6881	Approved
0.8058	Intermediate Similarity	NPD6011	Approved
0.8058	Intermediate Similarity	NPD6899	Approved
0.8039	Intermediate Similarity	NPD7128	Approved
0.8039	Intermediate Similarity	NPD5739	Approved
0.8039	Intermediate Similarity	NPD6675	Approved
0.8039	Intermediate Similarity	NPD6402	Approved
0.7981	Intermediate Similarity	NPD6013	Approved
0.7981	Intermediate Similarity	NPD6014	Approved
0.7981	Intermediate Similarity	NPD6012	Approved
0.798	Intermediate Similarity	NPD7638	Approved
0.7979	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD5701	Approved
0.7959	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5221	Approved
0.7959	Intermediate Similarity	NPD5222	Approved
0.7957	Intermediate Similarity	NPD6409	Approved
0.7957	Intermediate Similarity	NPD3618	Phase 1
0.7957	Intermediate Similarity	NPD6684	Approved
0.7957	Intermediate Similarity	NPD5330	Approved
0.7957	Intermediate Similarity	NPD7146	Approved
0.7957	Intermediate Similarity	NPD7521	Approved
0.7957	Intermediate Similarity	NPD7334	Approved
0.7905	Intermediate Similarity	NPD6883	Approved
0.7905	Intermediate Similarity	NPD7102	Approved
0.7905	Intermediate Similarity	NPD7290	Approved
0.79	Intermediate Similarity	NPD7640	Approved
0.79	Intermediate Similarity	NPD7639	Approved
0.7885	Intermediate Similarity	NPD7320	Approved
0.7879	Intermediate Similarity	NPD5173	Approved
0.7872	Intermediate Similarity	NPD3573	Approved
0.7835	Intermediate Similarity	NPD6399	Phase 3
0.783	Intermediate Similarity	NPD6650	Approved
0.783	Intermediate Similarity	NPD6617	Approved
0.783	Intermediate Similarity	NPD6649	Approved
0.783	Intermediate Similarity	NPD6869	Approved
0.783	Intermediate Similarity	NPD8130	Phase 1
0.783	Intermediate Similarity	NPD6847	Approved
0.781	Intermediate Similarity	NPD6373	Approved
0.781	Intermediate Similarity	NPD6372	Approved
0.7789	Intermediate Similarity	NPD5737	Approved
0.7789	Intermediate Similarity	NPD6903	Approved
0.7789	Intermediate Similarity	NPD6672	Approved
0.7757	Intermediate Similarity	NPD6882	Approved
0.7757	Intermediate Similarity	NPD8297	Approved
0.7755	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7900	Approved
0.7742	Intermediate Similarity	NPD3133	Approved
0.7742	Intermediate Similarity	NPD3665	Phase 1
0.7742	Intermediate Similarity	NPD3666	Approved
0.7732	Intermediate Similarity	NPD8034	Phase 2
0.7732	Intermediate Similarity	NPD8035	Phase 2
0.7723	Intermediate Similarity	NPD5286	Approved
0.7723	Intermediate Similarity	NPD5285	Approved
0.7723	Intermediate Similarity	NPD4696	Approved
0.7717	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD6083	Phase 2
0.77	Intermediate Similarity	NPD6084	Phase 2
0.77	Intermediate Similarity	NPD4755	Approved
0.7677	Intermediate Similarity	NPD5695	Phase 3
0.7664	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5223	Approved
0.7624	Intermediate Similarity	NPD5696	Approved
0.7579	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD5226	Approved
0.7573	Intermediate Similarity	NPD4633	Approved
0.7573	Intermediate Similarity	NPD5224	Approved
0.7573	Intermediate Similarity	NPD5211	Phase 2
0.7573	Intermediate Similarity	NPD5225	Approved
0.7549	Intermediate Similarity	NPD4700	Approved
0.7545	Intermediate Similarity	NPD6868	Approved
0.7545	Intermediate Similarity	NPD6274	Approved
0.7527	Intermediate Similarity	NPD3667	Approved
0.7524	Intermediate Similarity	NPD6008	Approved
0.7523	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5174	Approved
0.7477	Intermediate Similarity	NPD6317	Approved
0.7475	Intermediate Similarity	NPD4202	Approved
0.7429	Intermediate Similarity	NPD5141	Approved
0.7411	Intermediate Similarity	NPD6313	Approved
0.7411	Intermediate Similarity	NPD6314	Approved
0.7411	Intermediate Similarity	NPD6335	Approved
0.7374	Intermediate Similarity	NPD6411	Approved
0.7368	Intermediate Similarity	NPD4786	Approved
0.7347	Intermediate Similarity	NPD6673	Approved
0.7347	Intermediate Similarity	NPD6080	Approved
0.7347	Intermediate Similarity	NPD4753	Phase 2
0.7347	Intermediate Similarity	NPD6904	Approved
0.7345	Intermediate Similarity	NPD7101	Approved
0.7345	Intermediate Similarity	NPD7100	Approved
0.734	Intermediate Similarity	NPD4221	Approved
0.734	Intermediate Similarity	NPD4223	Phase 3
0.7333	Intermediate Similarity	NPD4754	Approved
0.7321	Intermediate Similarity	NPD6009	Approved
0.7312	Intermediate Similarity	NPD4695	Discontinued
0.7292	Intermediate Similarity	NPD1694	Approved
0.7282	Intermediate Similarity	NPD4225	Approved
0.7281	Intermediate Similarity	NPD6319	Approved
0.7265	Intermediate Similarity	NPD7507	Approved
0.7245	Intermediate Similarity	NPD5208	Approved
0.7238	Intermediate Similarity	NPD7632	Discontinued
0.7228	Intermediate Similarity	NPD6001	Approved
0.7222	Intermediate Similarity	NPD5128	Approved
0.7222	Intermediate Similarity	NPD5168	Approved
0.7222	Intermediate Similarity	NPD4730	Approved
0.7222	Intermediate Similarity	NPD4729	Approved
0.7217	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5983	Phase 2
0.7216	Intermediate Similarity	NPD5279	Phase 3
0.72	Intermediate Similarity	NPD5281	Approved
0.72	Intermediate Similarity	NPD5693	Phase 1
0.72	Intermediate Similarity	NPD5284	Approved
0.7196	Intermediate Similarity	NPD4767	Approved
0.7196	Intermediate Similarity	NPD4768	Approved
0.7188	Intermediate Similarity	NPD3668	Phase 3
0.7188	Intermediate Similarity	NPD4197	Approved
0.7172	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6101	Approved
0.7168	Intermediate Similarity	NPD7115	Discovery
0.7157	Intermediate Similarity	NPD5210	Approved
0.7157	Intermediate Similarity	NPD4629	Approved
0.7128	Intermediate Similarity	NPD7525	Registered
0.7113	Intermediate Similarity	NPD5329	Approved
0.71	Intermediate Similarity	NPD5692	Phase 3
0.7097	Intermediate Similarity	NPD3617	Approved
0.7094	Intermediate Similarity	NPD7604	Phase 2
0.7091	Intermediate Similarity	NPD4634	Approved
0.7091	Intermediate Similarity	NPD5169	Approved
0.7091	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5247	Approved
0.7091	Intermediate Similarity	NPD5250	Approved
0.7091	Intermediate Similarity	NPD5135	Approved
0.7091	Intermediate Similarity	NPD5248	Approved
0.7091	Intermediate Similarity	NPD5251	Approved
0.7091	Intermediate Similarity	NPD5249	Phase 3
0.7087	Intermediate Similarity	NPD7614	Phase 1
0.7083	Intermediate Similarity	NPD7319	Approved
0.7083	Intermediate Similarity	NPD4788	Approved
0.7069	Intermediate Similarity	NPD6909	Approved
0.7069	Intermediate Similarity	NPD6908	Approved
0.7065	Intermediate Similarity	NPD6117	Approved
0.7064	Intermediate Similarity	NPD6686	Approved
0.7041	Intermediate Similarity	NPD5205	Approved
0.7041	Intermediate Similarity	NPD4138	Approved
0.7041	Intermediate Similarity	NPD4689	Approved
0.7041	Intermediate Similarity	NPD4688	Approved
0.7041	Intermediate Similarity	NPD6098	Approved
0.7041	Intermediate Similarity	NPD4690	Approved
0.7041	Intermediate Similarity	NPD4623	Approved
0.7041	Intermediate Similarity	NPD4693	Phase 3
0.7041	Intermediate Similarity	NPD4519	Discontinued
0.7041	Intermediate Similarity	NPD5690	Phase 2
0.7034	Intermediate Similarity	NPD7492	Approved
0.703	Intermediate Similarity	NPD5694	Approved
0.703	Intermediate Similarity	NPD6050	Approved
0.7027	Intermediate Similarity	NPD5217	Approved
0.7027	Intermediate Similarity	NPD5215	Approved
0.7027	Intermediate Similarity	NPD5216	Approved
0.7027	Intermediate Similarity	NPD5127	Approved
0.7	Intermediate Similarity	NPD7736	Approved
0.699	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6116	Phase 1
0.6983	Remote Similarity	NPD6054	Approved
0.6975	Remote Similarity	NPD6616	Approved
0.6975	Remote Similarity	NPD6336	Discontinued
0.6972	Remote Similarity	NPD6412	Phase 2
0.6931	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD7732	Phase 3
0.6923	Remote Similarity	NPD6016	Approved
0.6923	Remote Similarity	NPD6015	Approved
0.6917	Remote Similarity	NPD7078	Approved
0.6915	Remote Similarity	NPD6115	Approved
0.6915	Remote Similarity	NPD6114	Approved
0.6915	Remote Similarity	NPD6697	Approved
0.6915	Remote Similarity	NPD6118	Approved
0.6889	Remote Similarity	NPD4691	Approved
0.6869	Remote Similarity	NPD5280	Approved
0.6869	Remote Similarity	NPD4694	Approved
0.6864	Remote Similarity	NPD6370	Approved
0.6864	Remote Similarity	NPD5988	Approved
0.6848	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4195	Approved
0.6842	Remote Similarity	NPD7645	Phase 2
0.6842	Remote Similarity	NPD5167	Approved
0.6838	Remote Similarity	NPD6059	Approved
0.6807	Remote Similarity	NPD8328	Phase 3
0.6804	Remote Similarity	NPD6435	Approved
0.6796	Remote Similarity	NPD5779	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