NPASS Compound

Structure

NPC473170 OpenBabel07101718202D 34 37 0 0 1 0 0 0 0 0999 V2000 3.0226 -2.8899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8104 -5.1591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0869 -5.8106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4472 0.4027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3416 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7693 -0.1860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4186 -3.4110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0701 -2.6874 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7693 -1.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7195 -4.3371 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0680 -5.0606 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1156 -4.8582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 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 -4.2162 -0.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6719 -4.5395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3689 -5.9867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1853 -3.9322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 17 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 28 1 0 0 0 0 11 29 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 21 1 0 0 0 0 14 22 1 0 0 0 0 15 18 1 0 0 0 0 15 27 1 0 0 0 0 16 1 1 6 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 30 2 0 0 0 0 19 21 2 0 0 0 0 20 27 1 6 0 0 0 21 28 1 0 0 0 0 22 24 1 0 0 0 0 22 31 1 6 0 0 0 23 25 1 0 0 0 0 23 32 1 6 0 0 0 24 27 1 1 0 0 0 24 29 1 0 0 0 0 25 26 1 0 0 0 0 25 33 1 1 0 0 0 26 34 1 0 0 0 0 27 5 1 6 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.33
Volume:	511.956
LogP:	3.306
LogD:	2.266
LogS:	-3.525
# Rotatable Bonds:	5
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.441
Synthetic Accessibility Score:	5.351
Fsp3:	0.828
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.271
MDCK Permeability:	9.681482879386749e-06
Pgp-inhibitor:	0.893
Pgp-substrate:	0.936
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.961
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.791
Plasma Protein Binding (PPB):	88.4508285522461%
Volume Distribution (VD):	0.976
Pgp-substrate:	2.7695367336273193%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.244
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.794
CYP3A4-substrate:	0.576

ADMET: Excretion

Clearance (CL):	4.135
Half-life (T1/2):	0.752

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.332
Skin Sensitization:	0.09
Carcinogencity:	0.084
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.501

Download Data

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

Natural Product: NPC473170

Natural Product ID:	NPC473170
*Common Name:**	DCYOPZMJKBYLCO-QJDZRUNDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DCYOPZMJKBYLCO-QJDZRUNDSA-N
Standard InCHI:	InChI=1S/C29H46O5/c1-16(13-23(32)25(33)26(3,4)34)19-8-10-28(6)21(19)14-22(31)24-27(5)15-18(30)12-17(2)20(27)9-11-29(24,28)7/h12,16,20,22-25,31-34H,8-11,13-15H2,1-7H3/t16-,20+,22+,23+,24+,25-,27+,28+,29+/m1/s1
SMILES:	CC1=CC(=O)CC2(C1CCC3(C2C(CC4=C(CCC43C)C(C)CC(C(C(C)(C)O)O)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3632950
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
IC50	1
Ki	1

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	IC50	=	2020.0	nM	PMID[524840]
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	Ki	=	1760.0	nM	PMID[524840]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	EC50	=	5640.0	nM	PMID[524841]

☑ 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 NPC473170 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	191
0.1-0.2	1190
0.2-0.3	4358
0.3-0.4	9700
0.4-0.5	12679
0.5-0.6	6527
0.6-0.7	5284
0.7-0.8	2474
0.8-0.85	253
0.85-0.9	33
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC473172
0.9032	High Similarity	NPC473164
0.9022	High Similarity	NPC472977
0.9022	High Similarity	NPC472976
0.9011	High Similarity	NPC155304
0.9	High Similarity	NPC31985
0.9	High Similarity	NPC32830
0.9	High Similarity	NPC1015
0.8989	High Similarity	NPC469314
0.8989	High Similarity	NPC469317
0.8989	High Similarity	NPC241875
0.8889	High Similarity	NPC328539
0.8817	High Similarity	NPC473162
0.8804	High Similarity	NPC185936
0.8804	High Similarity	NPC472978
0.8804	High Similarity	NPC473167
0.8804	High Similarity	NPC168027
0.8791	High Similarity	NPC77263
0.8791	High Similarity	NPC86319
0.8791	High Similarity	NPC119416
0.8791	High Similarity	NPC469319
0.8791	High Similarity	NPC229871
0.8791	High Similarity	NPC275740
0.8791	High Similarity	NPC250592
0.8778	High Similarity	NPC90652
0.8778	High Similarity	NPC475740
0.8764	High Similarity	NPC470574
0.8763	High Similarity	NPC473424
0.8763	High Similarity	NPC477915
0.875	High Similarity	NPC316964
0.875	High Similarity	NPC64600
0.8737	High Similarity	NPC18509
0.8737	High Similarity	NPC474938
0.8737	High Similarity	NPC474785
0.8723	High Similarity	NPC200702
0.8696	High Similarity	NPC85173
0.8687	High Similarity	NPC149047
0.8681	High Similarity	NPC131470
0.8681	High Similarity	NPC143767
0.8681	High Similarity	NPC471722
0.8681	High Similarity	NPC470417
0.8681	High Similarity	NPC158778
0.8673	High Similarity	NPC264048
0.8673	High Similarity	NPC191892
0.8667	High Similarity	NPC31564
0.8667	High Similarity	NPC474778
0.8667	High Similarity	NPC145879
0.8667	High Similarity	NPC474732
0.8667	High Similarity	NPC474733
0.8632	High Similarity	NPC471463
0.8632	High Similarity	NPC249954
0.8632	High Similarity	NPC117133
0.8617	High Similarity	NPC240617
0.8617	High Similarity	NPC196485
0.8617	High Similarity	NPC245972
0.8617	High Similarity	NPC471207
0.8617	High Similarity	NPC166906
0.8614	High Similarity	NPC214644
0.8614	High Similarity	NPC41405
0.8602	High Similarity	NPC473166
0.8602	High Similarity	NPC131872
0.86	High Similarity	NPC83744
0.86	High Similarity	NPC220229
0.86	High Similarity	NPC477916
0.86	High Similarity	NPC475060
0.8587	High Similarity	NPC472973
0.8587	High Similarity	NPC474245
0.8587	High Similarity	NPC186688
0.8586	High Similarity	NPC204833
0.8586	High Similarity	NPC209502
0.8571	High Similarity	NPC473163
0.8571	High Similarity	NPC58063
0.8557	High Similarity	NPC110149
0.8557	High Similarity	NPC144956
0.8556	High Similarity	NPC469948
0.8556	High Similarity	NPC197823
0.8539	High Similarity	NPC86370
0.8529	High Similarity	NPC5284
0.8526	High Similarity	NPC259286
0.8526	High Similarity	NPC317586
0.8526	High Similarity	NPC470016
0.8515	High Similarity	NPC329417
0.8515	High Similarity	NPC217201
0.8511	High Similarity	NPC109305
0.8511	High Similarity	NPC472930
0.8511	High Similarity	NPC69454
0.8511	High Similarity	NPC475255
0.8511	High Similarity	NPC274046
0.8511	High Similarity	NPC198074
0.85	High Similarity	NPC296945
0.85	High Similarity	NPC202167
0.85	High Similarity	NPC260268
0.85	High Similarity	NPC150531
0.85	High Similarity	NPC49958
0.85	High Similarity	NPC152695
0.85	High Similarity	NPC476027
0.85	High Similarity	NPC85829
0.85	High Similarity	NPC97202
0.85	High Similarity	NPC214264
0.85	High Similarity	NPC48733
0.85	High Similarity	NPC319077
0.85	High Similarity	NPC50692
0.85	High Similarity	NPC302607
0.85	High Similarity	NPC171137
0.8495	Intermediate Similarity	NPC183283
0.8495	Intermediate Similarity	NPC126993
0.8495	Intermediate Similarity	NPC48010
0.8478	Intermediate Similarity	NPC292491
0.8478	Intermediate Similarity	NPC310752
0.8478	Intermediate Similarity	NPC474677
0.8478	Intermediate Similarity	NPC53911
0.8469	Intermediate Similarity	NPC469327
0.8462	Intermediate Similarity	NPC72133
0.8454	Intermediate Similarity	NPC114274
0.8444	Intermediate Similarity	NPC85774
0.8444	Intermediate Similarity	NPC59453
0.8444	Intermediate Similarity	NPC221758
0.8444	Intermediate Similarity	NPC214043
0.8438	Intermediate Similarity	NPC96859
0.8438	Intermediate Similarity	NPC328162
0.8438	Intermediate Similarity	NPC305483
0.8438	Intermediate Similarity	NPC473158
0.8438	Intermediate Similarity	NPC192428
0.8431	Intermediate Similarity	NPC11710
0.8427	Intermediate Similarity	NPC151519
0.8427	Intermediate Similarity	NPC212083
0.8421	Intermediate Similarity	NPC103527
0.8421	Intermediate Similarity	NPC474690
0.8421	Intermediate Similarity	NPC8993
0.8421	Intermediate Similarity	NPC111015
0.8421	Intermediate Similarity	NPC196227
0.8416	Intermediate Similarity	NPC165873
0.8409	Intermediate Similarity	NPC2482
0.8404	Intermediate Similarity	NPC473998
0.8404	Intermediate Similarity	NPC475806
0.8404	Intermediate Similarity	NPC86266
0.8404	Intermediate Similarity	NPC110657
0.8404	Intermediate Similarity	NPC116726
0.8404	Intermediate Similarity	NPC272746
0.8404	Intermediate Similarity	NPC189520
0.8404	Intermediate Similarity	NPC63748
0.8404	Intermediate Similarity	NPC472975
0.8404	Intermediate Similarity	NPC212301
0.84	Intermediate Similarity	NPC75531
0.84	Intermediate Similarity	NPC149124
0.8387	Intermediate Similarity	NPC26959
0.8387	Intermediate Similarity	NPC309603
0.8387	Intermediate Similarity	NPC473999
0.8387	Intermediate Similarity	NPC268406
0.8387	Intermediate Similarity	NPC475921
0.8387	Intermediate Similarity	NPC477943
0.8387	Intermediate Similarity	NPC474704
0.837	Intermediate Similarity	NPC141292
0.837	Intermediate Similarity	NPC138756
0.837	Intermediate Similarity	NPC472324
0.8367	Intermediate Similarity	NPC83709
0.8365	Intermediate Similarity	NPC152117
0.8365	Intermediate Similarity	NPC234042
0.8351	Intermediate Similarity	NPC161147
0.8351	Intermediate Similarity	NPC473161
0.8351	Intermediate Similarity	NPC190554
0.8351	Intermediate Similarity	NPC108078
0.835	Intermediate Similarity	NPC239097
0.8333	Intermediate Similarity	NPC30677
0.8333	Intermediate Similarity	NPC37787
0.8333	Intermediate Similarity	NPC278648
0.8333	Intermediate Similarity	NPC139570
0.8333	Intermediate Similarity	NPC472932
0.8333	Intermediate Similarity	NPC280725
0.8333	Intermediate Similarity	NPC473415
0.8333	Intermediate Similarity	NPC65941
0.8333	Intermediate Similarity	NPC476082
0.8333	Intermediate Similarity	NPC469329
0.8333	Intermediate Similarity	NPC180950
0.8333	Intermediate Similarity	NPC180557
0.8333	Intermediate Similarity	NPC271195
0.8317	Intermediate Similarity	NPC323834
0.8317	Intermediate Similarity	NPC60681
0.8316	Intermediate Similarity	NPC474736
0.8316	Intermediate Similarity	NPC12722
0.8316	Intermediate Similarity	NPC107674
0.8316	Intermediate Similarity	NPC79117
0.8316	Intermediate Similarity	NPC134826
0.8316	Intermediate Similarity	NPC141497
0.8316	Intermediate Similarity	NPC170220
0.83	Intermediate Similarity	NPC311612
0.83	Intermediate Similarity	NPC247957
0.83	Intermediate Similarity	NPC475050
0.83	Intermediate Similarity	NPC249187
0.83	Intermediate Similarity	NPC239716
0.8298	Intermediate Similarity	NPC472325
0.8298	Intermediate Similarity	NPC136801
0.8298	Intermediate Similarity	NPC134321
0.8298	Intermediate Similarity	NPC191684
0.8298	Intermediate Similarity	NPC128672
0.8286	Intermediate Similarity	NPC73300
0.8286	Intermediate Similarity	NPC108721
0.8286	Intermediate Similarity	NPC255017
0.8283	Intermediate Similarity	NPC476897
0.828	Intermediate Similarity	NPC474925

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 NPC473170 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1548
0.2-0.3	3823
0.3-0.4	2410
0.4-0.5	740
0.5-0.6	161
0.6-0.7	152
0.7-0.8	110
0.8-0.85	31
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD5328	Approved
0.8804	High Similarity	NPD6079	Approved
0.8737	High Similarity	NPD4755	Approved
0.8667	High Similarity	NPD3618	Phase 1
0.8557	High Similarity	NPD4700	Approved
0.8557	High Similarity	NPD4696	Approved
0.8557	High Similarity	NPD5286	Approved
0.8557	High Similarity	NPD5285	Approved
0.8444	Intermediate Similarity	NPD4786	Approved
0.8438	Intermediate Similarity	NPD4697	Phase 3
0.8438	Intermediate Similarity	NPD5222	Approved
0.8438	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD5221	Approved
0.8427	Intermediate Similarity	NPD3667	Approved
0.8384	Intermediate Similarity	NPD5226	Approved
0.8384	Intermediate Similarity	NPD4633	Approved
0.8384	Intermediate Similarity	NPD5225	Approved
0.8384	Intermediate Similarity	NPD5224	Approved
0.8384	Intermediate Similarity	NPD5211	Phase 2
0.8351	Intermediate Similarity	NPD5173	Approved
0.8317	Intermediate Similarity	NPD6675	Approved
0.8317	Intermediate Similarity	NPD7128	Approved
0.8317	Intermediate Similarity	NPD5739	Approved
0.8317	Intermediate Similarity	NPD6402	Approved
0.8316	Intermediate Similarity	NPD4202	Approved
0.83	Intermediate Similarity	NPD5175	Approved
0.83	Intermediate Similarity	NPD5174	Approved
0.8283	Intermediate Similarity	NPD5223	Approved
0.8242	Intermediate Similarity	NPD3133	Approved
0.8242	Intermediate Similarity	NPD3665	Phase 1
0.8242	Intermediate Similarity	NPD3666	Approved
0.8218	Intermediate Similarity	NPD5141	Approved
0.8211	Intermediate Similarity	NPD7515	Phase 2
0.8191	Intermediate Similarity	NPD4753	Phase 2
0.8173	Intermediate Similarity	NPD4634	Approved
0.8155	Intermediate Similarity	NPD6881	Approved
0.8155	Intermediate Similarity	NPD7320	Approved
0.8155	Intermediate Similarity	NPD6899	Approved
0.8137	Intermediate Similarity	NPD4768	Approved
0.8137	Intermediate Similarity	NPD4767	Approved
0.8119	Intermediate Similarity	NPD4754	Approved
0.8077	Intermediate Similarity	NPD6372	Approved
0.8077	Intermediate Similarity	NPD6373	Approved
0.8058	Intermediate Similarity	NPD5697	Approved
0.8058	Intermediate Similarity	NPD5701	Approved
0.8019	Intermediate Similarity	NPD8297	Approved
0.8	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD7290	Approved
0.8	Intermediate Similarity	NPD6883	Approved
0.7981	Intermediate Similarity	NPD4729	Approved
0.7981	Intermediate Similarity	NPD4730	Approved
0.7981	Intermediate Similarity	NPD5128	Approved
0.7925	Intermediate Similarity	NPD6650	Approved
0.7925	Intermediate Similarity	NPD8130	Phase 1
0.7925	Intermediate Similarity	NPD6617	Approved
0.7925	Intermediate Similarity	NPD6869	Approved
0.7925	Intermediate Similarity	NPD6649	Approved
0.7925	Intermediate Similarity	NPD6847	Approved
0.7905	Intermediate Similarity	NPD6014	Approved
0.7905	Intermediate Similarity	NPD6012	Approved
0.7905	Intermediate Similarity	NPD6013	Approved
0.7872	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7748	Approved
0.785	Intermediate Similarity	NPD6882	Approved
0.7849	Intermediate Similarity	NPD3668	Phase 3
0.783	Intermediate Similarity	NPD5249	Phase 3
0.783	Intermediate Similarity	NPD5247	Approved
0.783	Intermediate Similarity	NPD5248	Approved
0.783	Intermediate Similarity	NPD5250	Approved
0.783	Intermediate Similarity	NPD5251	Approved
0.7826	Intermediate Similarity	NPD4223	Phase 3
0.7826	Intermediate Similarity	NPD4221	Approved
0.781	Intermediate Similarity	NPD6011	Approved
0.78	Intermediate Similarity	NPD6083	Phase 2
0.78	Intermediate Similarity	NPD6084	Phase 2
0.7778	Intermediate Similarity	NPD5210	Approved
0.7778	Intermediate Similarity	NPD4632	Approved
0.7778	Intermediate Similarity	NPD4629	Approved
0.7766	Intermediate Similarity	NPD5329	Approved
0.7757	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD5217	Approved
0.7757	Intermediate Similarity	NPD5215	Approved
0.7757	Intermediate Similarity	NPD5216	Approved
0.7755	Intermediate Similarity	NPD6399	Phase 3
0.7727	Intermediate Similarity	NPD7115	Discovery
0.7684	Intermediate Similarity	NPD5279	Phase 3
0.7664	Intermediate Similarity	NPD5169	Approved
0.7664	Intermediate Similarity	NPD5135	Approved
0.7664	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4197	Approved
0.7642	Intermediate Similarity	NPD5168	Approved
0.7624	Intermediate Similarity	NPD7902	Approved
0.7609	Intermediate Similarity	NPD4695	Discontinued
0.7609	Intermediate Similarity	NPD7525	Registered
0.7593	Intermediate Similarity	NPD5127	Approved
0.7547	Intermediate Similarity	NPD6412	Phase 2
0.7522	Intermediate Similarity	NPD6319	Approved
0.7522	Intermediate Similarity	NPD6059	Approved
0.7522	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD4693	Phase 3
0.75	Intermediate Similarity	NPD4623	Approved
0.75	Intermediate Similarity	NPD4690	Approved
0.75	Intermediate Similarity	NPD5205	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD4689	Approved
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD4688	Approved
0.75	Intermediate Similarity	NPD4138	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD4519	Discontinued
0.75	Intermediate Similarity	NPD5330	Approved
0.7477	Intermediate Similarity	NPD6274	Approved
0.7453	Intermediate Similarity	NPD6008	Approved
0.7444	Intermediate Similarity	NPD7339	Approved
0.7444	Intermediate Similarity	NPD6942	Approved
0.7434	Intermediate Similarity	NPD7100	Approved
0.7434	Intermediate Similarity	NPD7101	Approved
0.7426	Intermediate Similarity	NPD5695	Phase 3
0.7423	Intermediate Similarity	NPD3573	Approved
0.7411	Intermediate Similarity	NPD6009	Approved
0.7396	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6370	Approved
0.7391	Intermediate Similarity	NPD3617	Approved
0.7387	Intermediate Similarity	NPD5167	Approved
0.7379	Intermediate Similarity	NPD7638	Approved
0.7379	Intermediate Similarity	NPD5696	Approved
0.7368	Intermediate Similarity	NPD4788	Approved
0.7363	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6672	Approved
0.7347	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5737	Approved
0.7347	Intermediate Similarity	NPD6903	Approved
0.7345	Intermediate Similarity	NPD6335	Approved
0.7327	Intermediate Similarity	NPD7900	Approved
0.7327	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6868	Approved
0.732	Intermediate Similarity	NPD5690	Phase 2
0.732	Intermediate Similarity	NPD5280	Approved
0.732	Intermediate Similarity	NPD4694	Approved
0.7312	Intermediate Similarity	NPD7645	Phase 2
0.7308	Intermediate Similarity	NPD7640	Approved
0.7308	Intermediate Similarity	NPD7639	Approved
0.7304	Intermediate Similarity	NPD6908	Approved
0.7304	Intermediate Similarity	NPD6909	Approved
0.7304	Intermediate Similarity	NPD6016	Approved
0.7304	Intermediate Similarity	NPD6015	Approved
0.73	Intermediate Similarity	NPD6411	Approved
0.7265	Intermediate Similarity	NPD7492	Approved
0.7257	Intermediate Similarity	NPD6317	Approved
0.7255	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5988	Approved
0.7212	Intermediate Similarity	NPD4225	Approved
0.7203	Intermediate Similarity	NPD6616	Approved
0.7193	Intermediate Similarity	NPD6313	Approved
0.7193	Intermediate Similarity	NPD6314	Approved
0.7179	Intermediate Similarity	NPD7604	Phase 2
0.7174	Intermediate Similarity	NPD6933	Approved
0.7155	Intermediate Similarity	NPD5983	Phase 2
0.7143	Intermediate Similarity	NPD7078	Approved
0.7143	Intermediate Similarity	NPD8293	Discontinued
0.7129	Intermediate Similarity	NPD5284	Approved
0.7129	Intermediate Similarity	NPD5281	Approved
0.7128	Intermediate Similarity	NPD4195	Approved
0.71	Intermediate Similarity	NPD6904	Approved
0.71	Intermediate Similarity	NPD6101	Approved
0.71	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6080	Approved
0.71	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6673	Approved
0.7091	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7736	Approved
0.7079	Intermediate Similarity	NPD4137	Phase 3
0.7065	Intermediate Similarity	NPD3703	Phase 2
0.7059	Intermediate Similarity	NPD7507	Approved
0.7059	Intermediate Similarity	NPD6336	Discontinued
0.7053	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD1696	Phase 3
0.7034	Intermediate Similarity	NPD8328	Phase 3
0.7009	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4747	Approved
0.7	Intermediate Similarity	NPD4691	Approved
0.6961	Remote Similarity	NPD8034	Phase 2
0.6961	Remote Similarity	NPD8035	Phase 2
0.6957	Remote Similarity	NPD6926	Approved
0.6957	Remote Similarity	NPD6924	Approved
0.6942	Remote Similarity	NPD6033	Approved
0.6932	Remote Similarity	NPD7331	Phase 2
0.6923	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5290	Discontinued
0.6885	Remote Similarity	NPD7319	Approved
0.6875	Remote Similarity	NPD7509	Discontinued
0.6863	Remote Similarity	NPD4096	Approved
0.6847	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6686	Approved
0.6838	Remote Similarity	NPD4522	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