NPASS Compound

Structure

NPC253586 OpenBabel07101718302D 37 41 0 0 1 0 0 0 0 0999 V2000 -1.5422 -4.5611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2857 -3.4297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3447 1.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4163 2.2327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2938 -0.8918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4838 -0.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8646 -3.0093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2617 -2.1175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9209 -1.2301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2406 -3.6327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8938 -2.9072 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6908 0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6192 -0.3017 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8757 -1.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -1.9524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1100 -0.6745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6192 1.2778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -0.4881 0.0000 C 0 0 1 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 1.6908 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5362 -1.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6908 -1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1774 -2.3614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7130 0.2173 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0809 -0.7766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5289 -0.7076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1930 0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 8 36 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 29 1 0 0 0 0 12 31 1 0 0 0 0 13 14 1 0 0 0 0 13 28 1 0 0 0 0 14 31 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 16 23 1 0 0 0 0 18 17 1 6 0 0 0 18 24 1 0 0 0 0 19 24 1 0 0 0 0 19 28 1 6 0 0 0 20 25 1 0 0 0 0 20 32 1 6 0 0 0 21 27 1 0 0 0 0 21 30 1 1 0 0 0 22 30 1 6 0 0 0 22 37 1 0 0 0 0 23 33 2 0 0 0 0 23 36 1 0 0 0 0 24 31 1 1 0 0 0 25 29 1 1 0 0 0 25 30 1 0 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 27 37 1 0 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 7 1 1 0 0 0 31 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.35
Volume:	546.782
LogP:	4.597
LogD:	4.351
LogS:	-4.227
# Rotatable Bonds:	5
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.372
Synthetic Accessibility Score:	5.245
Fsp3:	0.871
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:	-5.435
MDCK Permeability:	2.9583450668724254e-05
Pgp-inhibitor:	0.06
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.633

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	80.66123962402344%
Volume Distribution (VD):	0.445
Pgp-substrate:	13.409614562988281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.454
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.15
CYP2C9-substrate:	0.194
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.349
CYP3A4-substrate:	0.28

ADMET: Excretion

Clearance (CL):	2.772
Half-life (T1/2):	0.493

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.411
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.131
Maximum Recommended Daily Dose:	0.303
Skin Sensitization:	0.23
Carcinogencity:	0.02
Eye Corrosion:	0.051
Eye Irritation:	0.163
Respiratory Toxicity:	0.902

Download Data

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

Natural Product: NPC253586

Natural Product ID:	NPC253586
*Common Name:**	Acanthosessiligenin Ii
IUPAC Name:	n.a.
Synonyms:	Acanthosessiligenin II
Standard InCHIKey:	GMWCFIADDGQIDG-KTJYCLMOSA-N
Standard InCHI:	InChI=1S/C31H48O6/c1-17(2)18-9-12-31(26(34)35)14-13-28(5)19(24(18)31)15-20(32)25-29(28,6)11-10-21-27(3,4)37-22(30(21,25)7)16-23(33)36-8/h18-22,24-25,32H,1,9-16H2,2-8H3,(H,34,35)/t18-,19+,20+,21-,22+,24+,25-,28+,29+,30+,31-/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](C[C@H]([C@H]4[C@@]3(C)CC[C@H]3C(C)(C)O[C@H](CC(=O)OC)[C@]43C)O)[C@@H]12)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063156
PubChem CID:	60154972
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003364] Steroid acids [CHEMONTID:0003368] 3-carboxy steroids

*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
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	Fruits	n.a.	n.a.	PMID[22691179]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	8
Others	1

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	<	10000.0	nM	PMID[574186]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[574186]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	<	10000.0	nM	PMID[574186]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	<	10000.0	nM	PMID[574186]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	<	10000.0	nM	PMID[574186]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	<	10000.0	nM	PMID[574186]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	IC50	<	10000.0	nM	PMID[574186]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	47000.0	nM	PMID[574186]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	91.1	%	PMID[574186]

☑ 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 NPC253586 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	223
0.1-0.2	1630
0.2-0.3	5898
0.3-0.4	13351
0.4-0.5	7658
0.5-0.6	5292
0.6-0.7	5670
0.7-0.8	2635
0.8-0.85	251
0.85-0.9	85
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC108371
0.9167	High Similarity	NPC124544
0.9032	High Similarity	NPC47853
0.8958	High Similarity	NPC94906
0.8936	High Similarity	NPC205173
0.8925	High Similarity	NPC287118
0.8925	High Similarity	NPC473690
0.8925	High Similarity	NPC471902
0.8866	High Similarity	NPC46848
0.8866	High Similarity	NPC75941
0.8854	High Similarity	NPC16911
0.8854	High Similarity	NPC78427
0.8854	High Similarity	NPC471038
0.8854	High Similarity	NPC119036
0.8854	High Similarity	NPC472028
0.8854	High Similarity	NPC474793
0.8842	High Similarity	NPC329910
0.8824	High Similarity	NPC272242
0.8817	High Similarity	NPC471901
0.8817	High Similarity	NPC475416
0.8804	High Similarity	NPC213832
0.8804	High Similarity	NPC57954
0.8776	High Similarity	NPC275990
0.8763	High Similarity	NPC41971
0.8763	High Similarity	NPC287676
0.8763	High Similarity	NPC180733
0.8763	High Similarity	NPC37047
0.875	High Similarity	NPC469810
0.8737	High Similarity	NPC470229
0.8737	High Similarity	NPC288906
0.8737	High Similarity	NPC279974
0.8737	High Similarity	NPC263135
0.8737	High Similarity	NPC470232
0.871	High Similarity	NPC10274
0.87	High Similarity	NPC472655
0.8696	High Similarity	NPC146937
0.8696	High Similarity	NPC471900
0.8687	High Similarity	NPC87927
0.8673	High Similarity	NPC39683
0.8673	High Similarity	NPC163963
0.8673	High Similarity	NPC289148
0.8673	High Similarity	NPC52899
0.8673	High Similarity	NPC236585
0.8667	High Similarity	NPC299963
0.866	High Similarity	NPC38296
0.866	High Similarity	NPC38471
0.866	High Similarity	NPC98837
0.866	High Similarity	NPC20479
0.866	High Similarity	NPC28864
0.866	High Similarity	NPC162459
0.8654	High Similarity	NPC102619
0.8646	High Similarity	NPC234564
0.8646	High Similarity	NPC200054
0.8646	High Similarity	NPC29410
0.8641	High Similarity	NPC470311
0.8632	High Similarity	NPC475118
0.8632	High Similarity	NPC470385
0.8632	High Similarity	NPC470386
0.8632	High Similarity	NPC277399
0.8617	High Similarity	NPC219516
0.8602	High Similarity	NPC471043
0.8587	High Similarity	NPC134197
0.8587	High Similarity	NPC264005
0.8587	High Similarity	NPC33768
0.8587	High Similarity	NPC269360
0.8586	High Similarity	NPC76866
0.8586	High Similarity	NPC246736
0.8586	High Similarity	NPC88203
0.8586	High Similarity	NPC214946
0.8586	High Similarity	NPC148628
0.8586	High Similarity	NPC286519
0.8586	High Similarity	NPC304832
0.8571	High Similarity	NPC477656
0.8571	High Similarity	NPC293866
0.8571	High Similarity	NPC477655
0.8571	High Similarity	NPC267921
0.8557	High Similarity	NPC190080
0.8557	High Similarity	NPC111187
0.8556	High Similarity	NPC471037
0.8542	High Similarity	NPC210214
0.8542	High Similarity	NPC98639
0.8529	High Similarity	NPC224414
0.8526	High Similarity	NPC199543
0.8526	High Similarity	NPC291373
0.8515	High Similarity	NPC200957
0.8515	High Similarity	NPC295366
0.8515	High Similarity	NPC138908
0.8515	High Similarity	NPC285927
0.8515	High Similarity	NPC37600
0.8511	High Similarity	NPC169933
0.85	High Similarity	NPC139347
0.85	High Similarity	NPC277074
0.85	High Similarity	NPC469985
0.85	High Similarity	NPC209298
0.85	High Similarity	NPC122811
0.8495	Intermediate Similarity	NPC250687
0.8495	Intermediate Similarity	NPC4309
0.8495	Intermediate Similarity	NPC211162
0.8495	Intermediate Similarity	NPC48824
0.8495	Intermediate Similarity	NPC254572
0.8495	Intermediate Similarity	NPC229407
0.8495	Intermediate Similarity	NPC183374
0.8485	Intermediate Similarity	NPC121218
0.8485	Intermediate Similarity	NPC253886
0.8478	Intermediate Similarity	NPC12774
0.8478	Intermediate Similarity	NPC2783
0.8469	Intermediate Similarity	NPC89099
0.8462	Intermediate Similarity	NPC473336
0.8462	Intermediate Similarity	NPC471044
0.8454	Intermediate Similarity	NPC470387
0.8454	Intermediate Similarity	NPC116683
0.8454	Intermediate Similarity	NPC327788
0.8447	Intermediate Similarity	NPC471250
0.8444	Intermediate Similarity	NPC472504
0.8431	Intermediate Similarity	NPC176949
0.8431	Intermediate Similarity	NPC59530
0.8431	Intermediate Similarity	NPC166993
0.8431	Intermediate Similarity	NPC61071
0.8431	Intermediate Similarity	NPC201908
0.8431	Intermediate Similarity	NPC96333
0.8431	Intermediate Similarity	NPC88833
0.8421	Intermediate Similarity	NPC470230
0.8421	Intermediate Similarity	NPC471747
0.8421	Intermediate Similarity	NPC211403
0.8421	Intermediate Similarity	NPC160506
0.8421	Intermediate Similarity	NPC198242
0.8416	Intermediate Similarity	NPC471293
0.8416	Intermediate Similarity	NPC101842
0.8416	Intermediate Similarity	NPC98603
0.8416	Intermediate Similarity	NPC13149
0.8404	Intermediate Similarity	NPC77001
0.8404	Intermediate Similarity	NPC253618
0.8404	Intermediate Similarity	NPC269267
0.84	Intermediate Similarity	NPC22388
0.84	Intermediate Similarity	NPC473788
0.84	Intermediate Similarity	NPC170615
0.84	Intermediate Similarity	NPC475558
0.8384	Intermediate Similarity	NPC470388
0.837	Intermediate Similarity	NPC294438
0.837	Intermediate Similarity	NPC264317
0.8367	Intermediate Similarity	NPC10864
0.8367	Intermediate Similarity	NPC170978
0.8365	Intermediate Similarity	NPC106760
0.8365	Intermediate Similarity	NPC101450
0.8351	Intermediate Similarity	NPC197158
0.8351	Intermediate Similarity	NPC471624
0.8351	Intermediate Similarity	NPC266431
0.835	Intermediate Similarity	NPC469845
0.835	Intermediate Similarity	NPC218123
0.835	Intermediate Similarity	NPC258323
0.835	Intermediate Similarity	NPC112895
0.835	Intermediate Similarity	NPC273155
0.835	Intermediate Similarity	NPC231278
0.8333	Intermediate Similarity	NPC244356
0.8333	Intermediate Similarity	NPC224060
0.8333	Intermediate Similarity	NPC475061
0.8333	Intermediate Similarity	NPC294263
0.8333	Intermediate Similarity	NPC470224
0.8317	Intermediate Similarity	NPC36688
0.8317	Intermediate Similarity	NPC216114
0.8317	Intermediate Similarity	NPC222153
0.8317	Intermediate Similarity	NPC140723
0.8317	Intermediate Similarity	NPC96217
0.8316	Intermediate Similarity	NPC194485
0.8316	Intermediate Similarity	NPC53890
0.8316	Intermediate Similarity	NPC219937
0.8316	Intermediate Similarity	NPC123252
0.8316	Intermediate Similarity	NPC46758
0.8302	Intermediate Similarity	NPC52634
0.83	Intermediate Similarity	NPC477052
0.83	Intermediate Similarity	NPC148279
0.83	Intermediate Similarity	NPC71706
0.83	Intermediate Similarity	NPC252614
0.83	Intermediate Similarity	NPC477053
0.83	Intermediate Similarity	NPC477051
0.8298	Intermediate Similarity	NPC16377
0.8298	Intermediate Similarity	NPC160304
0.8298	Intermediate Similarity	NPC255176
0.8298	Intermediate Similarity	NPC474719
0.8286	Intermediate Similarity	NPC11035
0.8286	Intermediate Similarity	NPC471251
0.8283	Intermediate Similarity	NPC164349
0.828	Intermediate Similarity	NPC80590
0.8269	Intermediate Similarity	NPC218853
0.8265	Intermediate Similarity	NPC256227
0.8265	Intermediate Similarity	NPC120708
0.8265	Intermediate Similarity	NPC13949
0.8261	Intermediate Similarity	NPC97505
0.8247	Intermediate Similarity	NPC303863
0.8247	Intermediate Similarity	NPC469982
0.8235	Intermediate Similarity	NPC47281
0.8235	Intermediate Similarity	NPC301787
0.8235	Intermediate Similarity	NPC84928
0.8229	Intermediate Similarity	NPC198054
0.8229	Intermediate Similarity	NPC250753
0.8229	Intermediate Similarity	NPC130840
0.8222	Intermediate Similarity	NPC206735
0.8218	Intermediate Similarity	NPC477054
0.8218	Intermediate Similarity	NPC193934
0.8218	Intermediate Similarity	NPC271980

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 NPC253586 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	2079
0.2-0.3	4042
0.3-0.4	1884
0.4-0.5	448
0.5-0.6	215
0.6-0.7	188
0.7-0.8	84
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD8035	Phase 2
0.8421	Intermediate Similarity	NPD8034	Phase 2
0.837	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6114	Approved
0.8	Intermediate Similarity	NPD6118	Approved
0.8	Intermediate Similarity	NPD6697	Approved
0.8	Intermediate Similarity	NPD6115	Approved
0.7921	Intermediate Similarity	NPD7638	Approved
0.7889	Intermediate Similarity	NPD6116	Phase 1
0.7843	Intermediate Similarity	NPD7639	Approved
0.7843	Intermediate Similarity	NPD7640	Approved
0.783	Intermediate Similarity	NPD7320	Approved
0.781	Intermediate Similarity	NPD5739	Approved
0.781	Intermediate Similarity	NPD6675	Approved
0.781	Intermediate Similarity	NPD7128	Approved
0.781	Intermediate Similarity	NPD6402	Approved
0.7778	Intermediate Similarity	NPD6399	Phase 3
0.7778	Intermediate Similarity	NPD6117	Approved
0.7739	Intermediate Similarity	NPD7492	Approved
0.7699	Intermediate Similarity	NPD6059	Approved
0.7699	Intermediate Similarity	NPD6054	Approved
0.7692	Intermediate Similarity	NPD7736	Approved
0.7672	Intermediate Similarity	NPD6616	Approved
0.7664	Intermediate Similarity	NPD6881	Approved
0.7664	Intermediate Similarity	NPD6899	Approved
0.7642	Intermediate Similarity	NPD6008	Approved
0.7636	Intermediate Similarity	NPD8133	Approved
0.7607	Intermediate Similarity	NPD8293	Discontinued
0.7607	Intermediate Similarity	NPD7078	Approved
0.7593	Intermediate Similarity	NPD6372	Approved
0.7593	Intermediate Similarity	NPD6373	Approved
0.757	Intermediate Similarity	NPD5697	Approved
0.757	Intermediate Similarity	NPD5701	Approved
0.7565	Intermediate Similarity	NPD6370	Approved
0.7556	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6319	Approved
0.7523	Intermediate Similarity	NPD7102	Approved
0.7523	Intermediate Similarity	NPD7290	Approved
0.7523	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD7319	Approved
0.7478	Intermediate Similarity	NPD6015	Approved
0.7478	Intermediate Similarity	NPD6016	Approved
0.7476	Intermediate Similarity	NPD6084	Phase 2
0.7476	Intermediate Similarity	NPD6083	Phase 2
0.7455	Intermediate Similarity	NPD8130	Phase 1
0.7455	Intermediate Similarity	NPD6869	Approved
0.7455	Intermediate Similarity	NPD6617	Approved
0.7455	Intermediate Similarity	NPD6650	Approved
0.7455	Intermediate Similarity	NPD6649	Approved
0.7455	Intermediate Similarity	NPD6847	Approved
0.7447	Intermediate Similarity	NPD7525	Registered
0.7431	Intermediate Similarity	NPD6013	Approved
0.7431	Intermediate Similarity	NPD6012	Approved
0.7431	Intermediate Similarity	NPD6014	Approved
0.7414	Intermediate Similarity	NPD5988	Approved
0.7396	Intermediate Similarity	NPD4788	Approved
0.7387	Intermediate Similarity	NPD6882	Approved
0.7387	Intermediate Similarity	NPD8297	Approved
0.7373	Intermediate Similarity	NPD7507	Approved
0.7358	Intermediate Similarity	NPD7632	Discontinued
0.7353	Intermediate Similarity	NPD7748	Approved
0.7339	Intermediate Similarity	NPD6011	Approved
0.7327	Intermediate Similarity	NPD7515	Phase 2
0.7321	Intermediate Similarity	NPD4632	Approved
0.732	Intermediate Similarity	NPD4786	Approved
0.7308	Intermediate Similarity	NPD7902	Approved
0.7308	Intermediate Similarity	NPD4755	Approved
0.73	Intermediate Similarity	NPD5328	Approved
0.7297	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7115	Discovery
0.7255	Intermediate Similarity	NPD4202	Approved
0.7207	Intermediate Similarity	NPD4634	Approved
0.7172	Intermediate Similarity	NPD3618	Phase 1
0.717	Intermediate Similarity	NPD5286	Approved
0.717	Intermediate Similarity	NPD4696	Approved
0.717	Intermediate Similarity	NPD4700	Approved
0.717	Intermediate Similarity	NPD5285	Approved
0.7157	Intermediate Similarity	NPD6079	Approved
0.7157	Intermediate Similarity	NPD7637	Suspended
0.7143	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6009	Approved
0.7117	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5695	Phase 3
0.7113	Intermediate Similarity	NPD3667	Approved
0.7107	Intermediate Similarity	NPD6033	Approved
0.7097	Intermediate Similarity	NPD3703	Phase 2
0.7091	Intermediate Similarity	NPD6412	Phase 2
0.7075	Intermediate Similarity	NPD5696	Approved
0.7069	Intermediate Similarity	NPD7328	Approved
0.7069	Intermediate Similarity	NPD7327	Approved
0.7059	Intermediate Similarity	NPD7604	Phase 2
0.7043	Intermediate Similarity	NPD6274	Approved
0.7037	Intermediate Similarity	NPD5224	Approved
0.7037	Intermediate Similarity	NPD5211	Phase 2
0.7037	Intermediate Similarity	NPD4633	Approved
0.7037	Intermediate Similarity	NPD5225	Approved
0.7037	Intermediate Similarity	NPD5226	Approved
0.7034	Intermediate Similarity	NPD5983	Phase 2
0.703	Intermediate Similarity	NPD5737	Approved
0.703	Intermediate Similarity	NPD6903	Approved
0.703	Intermediate Similarity	NPD6672	Approved
0.703	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7900	Approved
0.7019	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7101	Approved
0.7009	Intermediate Similarity	NPD7100	Approved
0.7009	Intermediate Similarity	NPD7516	Approved
0.7	Intermediate Similarity	NPD7521	Approved
0.7	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD5330	Approved
0.7	Intermediate Similarity	NPD6409	Approved
0.7	Intermediate Similarity	NPD7334	Approved
0.699	Remote Similarity	NPD6411	Approved
0.6983	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5174	Approved
0.6972	Remote Similarity	NPD5175	Approved
0.6964	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4753	Phase 2
0.6949	Remote Similarity	NPD8294	Approved
0.6949	Remote Similarity	NPD8377	Approved
0.6944	Remote Similarity	NPD1700	Approved
0.6944	Remote Similarity	NPD5223	Approved
0.6942	Remote Similarity	NPD6336	Discontinued
0.693	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD6335	Approved
0.6923	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD8328	Phase 3
0.6916	Remote Similarity	NPD4225	Approved
0.6915	Remote Similarity	NPD3702	Approved
0.6909	Remote Similarity	NPD5141	Approved
0.6909	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6928	Phase 2
0.6903	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD8379	Approved
0.6891	Remote Similarity	NPD8033	Approved
0.6891	Remote Similarity	NPD8335	Approved
0.6891	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD8296	Approved
0.6891	Remote Similarity	NPD8380	Approved
0.6891	Remote Similarity	NPD6908	Approved
0.6891	Remote Similarity	NPD6909	Approved
0.6891	Remote Similarity	NPD8378	Approved
0.6887	Remote Similarity	NPD5222	Approved
0.6887	Remote Similarity	NPD4697	Phase 3
0.6887	Remote Similarity	NPD5221	Approved
0.6887	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6686	Approved
0.6857	Remote Similarity	NPD6001	Approved
0.6847	Remote Similarity	NPD4768	Approved
0.6847	Remote Similarity	NPD4767	Approved
0.6838	Remote Similarity	NPD6317	Approved
0.6832	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6098	Approved
0.6822	Remote Similarity	NPD5173	Approved
0.6818	Remote Similarity	NPD4754	Approved
0.6813	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5360	Phase 3
0.68	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3666	Approved
0.68	Remote Similarity	NPD3665	Phase 1
0.68	Remote Similarity	NPD3133	Approved
0.6796	Remote Similarity	NPD6080	Approved
0.6796	Remote Similarity	NPD6673	Approved
0.6796	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6904	Approved
0.6796	Remote Similarity	NPD6101	Approved
0.678	Remote Similarity	NPD6313	Approved
0.678	Remote Similarity	NPD6314	Approved
0.6777	Remote Similarity	NPD6067	Discontinued
0.6774	Remote Similarity	NPD5777	Approved
0.6774	Remote Similarity	NPD6081	Approved
0.6762	Remote Similarity	NPD5779	Approved
0.6762	Remote Similarity	NPD5778	Approved
0.6752	Remote Similarity	NPD6868	Approved
0.675	Remote Similarity	NPD6921	Approved
0.6739	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4730	Approved
0.6726	Remote Similarity	NPD4729	Approved
0.6726	Remote Similarity	NPD5128	Approved
0.67	Remote Similarity	NPD6695	Phase 3
0.6698	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD4245	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6637	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5210	Approved
0.6636	Remote Similarity	NPD4629	Approved
0.6634	Remote Similarity	NPD3668	Phase 3
0.6633	Remote Similarity	NPD7645	Phase 2
0.6609	Remote Similarity	NPD5251	Approved
0.6609	Remote Similarity	NPD5250	Approved
0.6609	Remote Similarity	NPD5249	Phase 3
0.6609	Remote Similarity	NPD5247	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