NPASS Compound

Structure

NPC191892 OpenBabel07101718312D 37 40 0 0 1 0 0 0 0 0999 V2000 2.9855 2.6396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2424 3.3087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 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 -2.0032 1.9292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0563 2.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 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 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0345 2.3305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 2 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 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 2.3435 1.3795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2111 0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 9 10 1 0 0 0 0 9 16 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 14 27 1 0 0 0 0 15 22 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 17 29 1 6 0 0 0 18 24 1 0 0 0 0 18 31 1 6 0 0 0 19 23 1 0 0 0 0 19 32 1 1 0 0 0 20 27 1 1 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 21 33 2 0 0 0 0 22 29 1 0 0 0 0 22 34 2 0 0 0 0 23 28 1 6 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 35 1 1 0 0 0 25 36 1 0 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 30 8 1 6 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	520.34
Volume:	546.832
LogP:	2.484
LogD:	2.44
LogS:	-4.244
# Rotatable Bonds:	5
TPSA:	135.29
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	5.402
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
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:	-4.869
MDCK Permeability:	1.147355760622304e-05
Pgp-inhibitor:	0.937
Pgp-substrate:	0.053
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.877
30% Bioavailability (F30%):	0.493

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.77
Plasma Protein Binding (PPB):	66.17054748535156%
Volume Distribution (VD):	0.463
Pgp-substrate:	19.64903450012207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.785
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.476
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.61
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	5.44
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.633
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.119
Carcinogencity:	0.747
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.521

Download Data

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

Natural Product: NPC191892

Natural Product ID:	NPC191892
*Common Name:**	25-Deacetyl Hemslecin A
IUPAC Name:	(2S,3S,8S,9R,10R,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
Synonyms:	23,24-Dihydrocucurbitacin F; 25-Deacetyl Hemslecin A
Standard InCHIKey:	VVBWBGOEAVGFTN-LPQIEKFGSA-N
Standard InCHI:	InChI=1S/C30H48O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,17-20,23-24,31-32,35-37H,10-15H2,1-8H3/t17-,18+,19-,20+,23+,24-,27+,28-,29+,30+/m1/s1
SMILES:	CC(C)(CCC(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2(C)[C@@H]3CC=C4[C@@H](C[C@@H]([C@H](C4(C)C)O)O)[C@]3(C)C(=O)C[C@]12C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486260
PubChem CID:	10481797
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO33474	hemsleya penxianensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717151]
NPO12307	Elaeocarpus dolichostylus	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6549470]
NPO12307	Elaeocarpus dolichostylus	Species	Elaeocarpaceae	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
ED50	2
IC50	6
Others	4

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Organism	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[564733]
NPT168	Cell Line	P388	Mus musculus	ED50	>	50.0	ug ml-1	PMID[564733]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	1.03	ug.mL-1	PMID[564735]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	0.64	ug.mL-1	PMID[564735]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.9	n.a.	PMID[564734]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	31400.0	nM	PMID[564734]
NPT2	Others	Unspecified		Ratio CC50/IC50	<	1.0	n.a.	PMID[564734]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	60600.0	nM	PMID[564734]
NPT27	Others	Unspecified		CC50	=	60600.0	nM	PMID[564734]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.09	ug.mL-1	PMID[564735]

☑ 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 NPC191892 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	205
0.1-0.2	1361
0.2-0.3	4874
0.3-0.4	10431
0.4-0.5	11318
0.5-0.6	6080
0.6-0.7	5772
0.7-0.8	2353
0.8-0.85	217
0.85-0.9	50
0.9-0.95	34
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9694	High Similarity	NPC165873
0.9368	High Similarity	NPC49371
0.9223	High Similarity	NPC280782
0.92	High Similarity	NPC149047
0.9192	High Similarity	NPC117185
0.9135	High Similarity	NPC108721
0.9135	High Similarity	NPC73300
0.9118	High Similarity	NPC214644
0.9109	High Similarity	NPC475060
0.9109	High Similarity	NPC83744
0.9109	High Similarity	NPC477916
0.9109	High Similarity	NPC220229
0.91	High Similarity	NPC204833
0.91	High Similarity	NPC209502
0.9082	High Similarity	NPC15390
0.902	High Similarity	NPC329417
0.902	High Similarity	NPC217201
0.901	High Similarity	NPC85829
0.901	High Similarity	NPC49958
0.901	High Similarity	NPC302607
0.901	High Similarity	NPC214264
0.901	High Similarity	NPC202167
0.901	High Similarity	NPC50692
0.901	High Similarity	NPC97202
0.901	High Similarity	NPC319077
0.901	High Similarity	NPC150531
0.901	High Similarity	NPC476027
0.901	High Similarity	NPC152695
0.901	High Similarity	NPC171137
0.901	High Similarity	NPC48733
0.901	High Similarity	NPC296945
0.901	High Similarity	NPC260268
0.8932	High Similarity	NPC11710
0.89	High Similarity	NPC477915
0.8889	High Similarity	NPC83709
0.8889	High Similarity	NPC110149
0.8878	High Similarity	NPC18509
0.8878	High Similarity	NPC190554
0.8824	High Similarity	NPC257353
0.8824	High Similarity	NPC166607
0.8763	High Similarity	NPC245972
0.8763	High Similarity	NPC196485
0.8737	High Similarity	NPC32830
0.8737	High Similarity	NPC474245
0.8737	High Similarity	NPC76879
0.8725	High Similarity	NPC137657
0.8725	High Similarity	NPC160843
0.87	High Similarity	NPC144956
0.87	High Similarity	NPC474720
0.8679	High Similarity	NPC207251
0.8673	High Similarity	NPC472485
0.8673	High Similarity	NPC473170
0.8673	High Similarity	NPC200702
0.8667	High Similarity	NPC235077
0.8667	High Similarity	NPC76084
0.8654	High Similarity	NPC65941
0.8646	High Similarity	NPC136801
0.8641	High Similarity	NPC196528
0.8627	High Similarity	NPC311612
0.8627	High Similarity	NPC249187
0.8627	High Similarity	NPC247957
0.86	High Similarity	NPC191565
0.86	High Similarity	NPC477854
0.8598	High Similarity	NPC317210
0.8586	High Similarity	NPC477853
0.8586	High Similarity	NPC173272
0.8571	High Similarity	NPC111015
0.8558	High Similarity	NPC58370
0.8558	High Similarity	NPC185
0.8558	High Similarity	NPC43285
0.8557	High Similarity	NPC185936
0.8557	High Similarity	NPC168027
0.8544	High Similarity	NPC477812
0.8544	High Similarity	NPC149124
0.8544	High Similarity	NPC72255
0.8544	High Similarity	NPC471293
0.8544	High Similarity	NPC75531
0.8532	High Similarity	NPC471854
0.8529	High Similarity	NPC473424
0.8529	High Similarity	NPC87351
0.8526	High Similarity	NPC90652
0.8519	High Similarity	NPC326542
0.8515	High Similarity	NPC154072
0.8515	High Similarity	NPC316964
0.85	High Similarity	NPC170978
0.8485	Intermediate Similarity	NPC48330
0.8482	Intermediate Similarity	NPC222688
0.8476	Intermediate Similarity	NPC94529
0.8455	Intermediate Similarity	NPC311554
0.8455	Intermediate Similarity	NPC257457
0.8454	Intermediate Similarity	NPC46758
0.8438	Intermediate Similarity	NPC193360
0.8438	Intermediate Similarity	NPC470417
0.8426	Intermediate Similarity	NPC250109
0.8426	Intermediate Similarity	NPC194100
0.8426	Intermediate Similarity	NPC962
0.8421	Intermediate Similarity	NPC51014
0.8421	Intermediate Similarity	NPC20688
0.84	Intermediate Similarity	NPC192428
0.8396	Intermediate Similarity	NPC470257
0.8381	Intermediate Similarity	NPC144459
0.8381	Intermediate Similarity	NPC59530
0.8367	Intermediate Similarity	NPC155304
0.8367	Intermediate Similarity	NPC189520
0.8365	Intermediate Similarity	NPC29705
0.8351	Intermediate Similarity	NPC477943
0.8351	Intermediate Similarity	NPC186688
0.8351	Intermediate Similarity	NPC310010
0.8351	Intermediate Similarity	NPC31985
0.8351	Intermediate Similarity	NPC326627
0.8351	Intermediate Similarity	NPC1015
0.835	Intermediate Similarity	NPC477054
0.835	Intermediate Similarity	NPC185530
0.8333	Intermediate Similarity	NPC71348
0.8333	Intermediate Similarity	NPC138756
0.8316	Intermediate Similarity	NPC474218
0.8304	Intermediate Similarity	NPC109973
0.8304	Intermediate Similarity	NPC471406
0.83	Intermediate Similarity	NPC272617
0.83	Intermediate Similarity	NPC127063
0.83	Intermediate Similarity	NPC472824
0.83	Intermediate Similarity	NPC271195
0.83	Intermediate Similarity	NPC469599
0.8286	Intermediate Similarity	NPC231530
0.8286	Intermediate Similarity	NPC278628
0.8286	Intermediate Similarity	NPC323834
0.8283	Intermediate Similarity	NPC470376
0.8283	Intermediate Similarity	NPC470375
0.8283	Intermediate Similarity	NPC233118
0.8283	Intermediate Similarity	NPC206810
0.8283	Intermediate Similarity	NPC472496
0.8273	Intermediate Similarity	NPC266728
0.8273	Intermediate Similarity	NPC49492
0.8269	Intermediate Similarity	NPC140723
0.8269	Intermediate Similarity	NPC111323
0.8269	Intermediate Similarity	NPC26478
0.8269	Intermediate Similarity	NPC471005
0.8265	Intermediate Similarity	NPC171441
0.8257	Intermediate Similarity	NPC202889
0.8252	Intermediate Similarity	NPC477053
0.8252	Intermediate Similarity	NPC477051
0.8252	Intermediate Similarity	NPC477052
0.8247	Intermediate Similarity	NPC328539
0.8247	Intermediate Similarity	NPC471941
0.8247	Intermediate Similarity	NPC328313
0.8247	Intermediate Similarity	NPC53911
0.8241	Intermediate Similarity	NPC43775
0.8235	Intermediate Similarity	NPC114274
0.823	Intermediate Similarity	NPC470921
0.8218	Intermediate Similarity	NPC305483
0.8218	Intermediate Similarity	NPC96859
0.8218	Intermediate Similarity	NPC328162
0.8214	Intermediate Similarity	NPC475041
0.8211	Intermediate Similarity	NPC59453
0.8211	Intermediate Similarity	NPC82902
0.8211	Intermediate Similarity	NPC221758
0.8208	Intermediate Similarity	NPC144854
0.8208	Intermediate Similarity	NPC3316
0.8208	Intermediate Similarity	NPC44063
0.82	Intermediate Similarity	NPC280804
0.82	Intermediate Similarity	NPC209662
0.819	Intermediate Similarity	NPC284865
0.8174	Intermediate Similarity	NPC473255
0.8173	Intermediate Similarity	NPC271980
0.8173	Intermediate Similarity	NPC22388
0.8173	Intermediate Similarity	NPC193934
0.8173	Intermediate Similarity	NPC473928
0.8163	Intermediate Similarity	NPC77263
0.8163	Intermediate Similarity	NPC86319
0.8163	Intermediate Similarity	NPC474704
0.8163	Intermediate Similarity	NPC250592
0.8163	Intermediate Similarity	NPC105495
0.8163	Intermediate Similarity	NPC275740
0.8163	Intermediate Similarity	NPC475921
0.8158	Intermediate Similarity	NPC65858
0.8155	Intermediate Similarity	NPC291785
0.8155	Intermediate Similarity	NPC218383
0.8155	Intermediate Similarity	NPC127408
0.8144	Intermediate Similarity	NPC469314
0.8144	Intermediate Similarity	NPC475740
0.8144	Intermediate Similarity	NPC472481
0.8144	Intermediate Similarity	NPC472482
0.8144	Intermediate Similarity	NPC317590
0.8144	Intermediate Similarity	NPC241875
0.8144	Intermediate Similarity	NPC469317
0.8144	Intermediate Similarity	NPC472484
0.8137	Intermediate Similarity	NPC108078
0.8131	Intermediate Similarity	NPC154608
0.8131	Intermediate Similarity	NPC192813
0.8131	Intermediate Similarity	NPC9013
0.8131	Intermediate Similarity	NPC277017
0.8119	Intermediate Similarity	NPC472932
0.8113	Intermediate Similarity	NPC60681
0.8108	Intermediate Similarity	NPC96312
0.8108	Intermediate Similarity	NPC148458
0.8108	Intermediate Similarity	NPC40632
0.8108	Intermediate Similarity	NPC328374
0.8108	Intermediate Similarity	NPC270958
0.8108	Intermediate Similarity	NPC251236
0.8105	Intermediate Similarity	NPC278648

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 NPC191892 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1669
0.2-0.3	4087
0.3-0.4	2136
0.4-0.5	594
0.5-0.6	168
0.6-0.7	146
0.7-0.8	98
0.8-0.85	58
0.85-0.9	14
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8878	High Similarity	NPD4755	Approved
0.87	High Similarity	NPD5286	Approved
0.87	High Similarity	NPD4696	Approved
0.87	High Similarity	NPD5285	Approved
0.87	High Similarity	NPD4700	Approved
0.8667	High Similarity	NPD4634	Approved
0.8529	High Similarity	NPD5211	Phase 2
0.8529	High Similarity	NPD5225	Approved
0.8529	High Similarity	NPD5224	Approved
0.8529	High Similarity	NPD4633	Approved
0.8529	High Similarity	NPD5226	Approved
0.8462	Intermediate Similarity	NPD7128	Approved
0.8462	Intermediate Similarity	NPD6675	Approved
0.8462	Intermediate Similarity	NPD6402	Approved
0.8462	Intermediate Similarity	NPD5739	Approved
0.8447	Intermediate Similarity	NPD5175	Approved
0.8447	Intermediate Similarity	NPD5174	Approved
0.8431	Intermediate Similarity	NPD5223	Approved
0.84	Intermediate Similarity	NPD4697	Phase 3
0.8396	Intermediate Similarity	NPD6372	Approved
0.8396	Intermediate Similarity	NPD6373	Approved
0.8365	Intermediate Similarity	NPD5141	Approved
0.8351	Intermediate Similarity	NPD5328	Approved
0.8351	Intermediate Similarity	NPD4753	Phase 2
0.8302	Intermediate Similarity	NPD7320	Approved
0.8302	Intermediate Similarity	NPD6899	Approved
0.8302	Intermediate Similarity	NPD6881	Approved
0.8286	Intermediate Similarity	NPD4767	Approved
0.8286	Intermediate Similarity	NPD4768	Approved
0.8269	Intermediate Similarity	NPD4754	Approved
0.8257	Intermediate Similarity	NPD4632	Approved
0.8241	Intermediate Similarity	NPD6649	Approved
0.8241	Intermediate Similarity	NPD6650	Approved
0.8218	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD5221	Approved
0.8218	Intermediate Similarity	NPD5222	Approved
0.8211	Intermediate Similarity	NPD4786	Approved
0.8208	Intermediate Similarity	NPD5697	Approved
0.8208	Intermediate Similarity	NPD5701	Approved
0.8182	Intermediate Similarity	NPD6079	Approved
0.8165	Intermediate Similarity	NPD8297	Approved
0.8148	Intermediate Similarity	NPD6883	Approved
0.8148	Intermediate Similarity	NPD7102	Approved
0.8148	Intermediate Similarity	NPD7290	Approved
0.8137	Intermediate Similarity	NPD5173	Approved
0.8131	Intermediate Similarity	NPD4730	Approved
0.8131	Intermediate Similarity	NPD5128	Approved
0.8131	Intermediate Similarity	NPD4729	Approved
0.8119	Intermediate Similarity	NPD4629	Approved
0.8119	Intermediate Similarity	NPD5210	Approved
0.81	Intermediate Similarity	NPD4202	Approved
0.8073	Intermediate Similarity	NPD6869	Approved
0.8073	Intermediate Similarity	NPD6847	Approved
0.8073	Intermediate Similarity	NPD8130	Phase 1
0.8073	Intermediate Similarity	NPD6617	Approved
0.8056	Intermediate Similarity	NPD6014	Approved
0.8056	Intermediate Similarity	NPD6013	Approved
0.8056	Intermediate Similarity	NPD6012	Approved
0.8041	Intermediate Similarity	NPD3618	Phase 1
0.8	Intermediate Similarity	NPD3667	Approved
0.8	Intermediate Similarity	NPD6882	Approved
0.7982	Intermediate Similarity	NPD5249	Phase 3
0.7982	Intermediate Similarity	NPD5251	Approved
0.7982	Intermediate Similarity	NPD5250	Approved
0.7982	Intermediate Similarity	NPD5247	Approved
0.7982	Intermediate Similarity	NPD6059	Approved
0.7982	Intermediate Similarity	NPD6319	Approved
0.7982	Intermediate Similarity	NPD5248	Approved
0.7982	Intermediate Similarity	NPD6054	Approved
0.7963	Intermediate Similarity	NPD6011	Approved
0.7961	Intermediate Similarity	NPD6083	Phase 2
0.7961	Intermediate Similarity	NPD6084	Phase 2
0.7938	Intermediate Similarity	NPD5329	Approved
0.7909	Intermediate Similarity	NPD5215	Approved
0.7909	Intermediate Similarity	NPD5216	Approved
0.7909	Intermediate Similarity	NPD5217	Approved
0.7909	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD6009	Approved
0.7845	Intermediate Similarity	NPD6370	Approved
0.7835	Intermediate Similarity	NPD3666	Approved
0.7835	Intermediate Similarity	NPD3133	Approved
0.7835	Intermediate Similarity	NPD3665	Phase 1
0.7835	Intermediate Similarity	NPD4197	Approved
0.7818	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5135	Approved
0.7818	Intermediate Similarity	NPD5169	Approved
0.7778	Intermediate Similarity	NPD6008	Approved
0.7759	Intermediate Similarity	NPD6015	Approved
0.7759	Intermediate Similarity	NPD6016	Approved
0.7748	Intermediate Similarity	NPD5127	Approved
0.7745	Intermediate Similarity	NPD6399	Phase 3
0.7714	Intermediate Similarity	NPD5696	Approved
0.7712	Intermediate Similarity	NPD7492	Approved
0.7692	Intermediate Similarity	NPD5988	Approved
0.7647	Intermediate Similarity	NPD6616	Approved
0.7632	Intermediate Similarity	NPD6274	Approved
0.7629	Intermediate Similarity	NPD4221	Approved
0.7629	Intermediate Similarity	NPD4223	Phase 3
0.7627	Intermediate Similarity	NPD7604	Phase 2
0.7607	Intermediate Similarity	NPD5983	Phase 2
0.7596	Intermediate Similarity	NPD5695	Phase 3
0.7586	Intermediate Similarity	NPD7101	Approved
0.7586	Intermediate Similarity	NPD7100	Approved
0.7583	Intermediate Similarity	NPD7078	Approved
0.7583	Intermediate Similarity	NPD8293	Discontinued
0.7545	Intermediate Similarity	NPD6412	Phase 2
0.7544	Intermediate Similarity	NPD5167	Approved
0.7521	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD6336	Discontinued
0.75	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD5280	Approved
0.75	Intermediate Similarity	NPD4694	Approved
0.75	Intermediate Similarity	NPD5279	Phase 3
0.7477	Intermediate Similarity	NPD5168	Approved
0.7475	Intermediate Similarity	NPD3668	Phase 3
0.7458	Intermediate Similarity	NPD6909	Approved
0.7458	Intermediate Similarity	NPD6908	Approved
0.7423	Intermediate Similarity	NPD7525	Registered
0.7414	Intermediate Similarity	NPD7115	Discovery
0.7414	Intermediate Similarity	NPD6317	Approved
0.7377	Intermediate Similarity	NPD6033	Approved
0.7374	Intermediate Similarity	NPD4788	Approved
0.7368	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6314	Approved
0.735	Intermediate Similarity	NPD6313	Approved
0.7327	Intermediate Similarity	NPD4688	Approved
0.7327	Intermediate Similarity	NPD6098	Approved
0.7327	Intermediate Similarity	NPD4690	Approved
0.7327	Intermediate Similarity	NPD4693	Phase 3
0.7327	Intermediate Similarity	NPD4689	Approved
0.7327	Intermediate Similarity	NPD4138	Approved
0.7327	Intermediate Similarity	NPD5205	Approved
0.7321	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7515	Phase 2
0.7288	Intermediate Similarity	NPD4522	Approved
0.7282	Intermediate Similarity	NPD6904	Approved
0.7282	Intermediate Similarity	NPD6080	Approved
0.7282	Intermediate Similarity	NPD6673	Approved
0.7264	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7339	Approved
0.7263	Intermediate Similarity	NPD6942	Approved
0.7255	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7638	Approved
0.7213	Intermediate Similarity	NPD7507	Approved
0.7184	Intermediate Similarity	NPD5737	Approved
0.7184	Intermediate Similarity	NPD6672	Approved
0.7179	Intermediate Similarity	NPD6868	Approved
0.7157	Intermediate Similarity	NPD7146	Approved
0.7157	Intermediate Similarity	NPD7521	Approved
0.7157	Intermediate Similarity	NPD7334	Approved
0.7157	Intermediate Similarity	NPD6409	Approved
0.7157	Intermediate Similarity	NPD6684	Approved
0.7157	Intermediate Similarity	NPD5330	Approved
0.7156	Intermediate Similarity	NPD7640	Approved
0.7156	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD5281	Approved
0.7143	Intermediate Similarity	NPD5284	Approved
0.7087	Intermediate Similarity	NPD7524	Approved
0.7083	Intermediate Similarity	NPD3703	Phase 2
0.7071	Intermediate Similarity	NPD4695	Discontinued
0.7049	Intermediate Similarity	NPD8328	Phase 3
0.7041	Intermediate Similarity	NPD3617	Approved
0.704	Intermediate Similarity	NPD7319	Approved
0.7027	Intermediate Similarity	NPD5091	Approved
0.7019	Intermediate Similarity	NPD6903	Approved
0.7019	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6933	Approved
0.7009	Intermediate Similarity	NPD7748	Approved
0.7	Intermediate Similarity	NPD4692	Approved
0.7	Intermediate Similarity	NPD4139	Approved
0.6981	Remote Similarity	NPD5693	Phase 1
0.6981	Remote Similarity	NPD6050	Approved
0.6981	Remote Similarity	NPD8035	Phase 2
0.6981	Remote Similarity	NPD8034	Phase 2
0.6979	Remote Similarity	NPD4785	Approved
0.6979	Remote Similarity	NPD4784	Approved
0.6975	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7902	Approved
0.697	Remote Similarity	NPD4195	Approved
0.6957	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4243	Approved
0.6923	Remote Similarity	NPD6053	Discontinued
0.6916	Remote Similarity	NPD5133	Approved
0.69	Remote Similarity	NPD4748	Discontinued
0.69	Remote Similarity	NPD6931	Approved
0.69	Remote Similarity	NPD6930	Phase 2
0.6887	Remote Similarity	NPD5692	Phase 3
0.6869	Remote Similarity	NPD6115	Approved
0.6869	Remote Similarity	NPD6697	Approved
0.6869	Remote Similarity	NPD6118	Approved
0.6869	Remote Similarity	NPD6114	Approved
0.6863	Remote Similarity	NPD6695	Phase 3
0.6852	Remote Similarity	NPD6001	Approved
0.6822	Remote Similarity	NPD6411	Approved
0.6822	Remote Similarity	NPD5694	Approved
0.681	Remote Similarity	NPD4061	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data