NPASS Compound

Structure

NPC473424 OpenBabel07101719522D 32 35 0 0 1 0 0 0 0 0999 V2000 -2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9792 -6.0914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 -5.4223 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 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 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 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1871 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -5.3212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 24 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 19 2 0 0 0 0 13 21 1 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 15 25 1 0 0 0 0 16 1 1 1 0 0 0 16 17 1 0 0 0 0 17 26 1 1 0 0 0 18 19 1 0 0 0 0 18 25 1 1 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 21 28 2 0 0 0 0 22 23 1 0 0 0 0 22 29 1 6 0 0 0 23 30 1 6 0 0 0 24 31 1 0 0 0 0 25 4 1 1 0 0 0 26 27 1 1 0 0 0 27 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.3
Volume:	477.364
LogP:	3.325
LogD:	3.439
LogS:	-4.393
# Rotatable Bonds:	5
TPSA:	91.67
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.616
Synthetic Accessibility Score:	4.825
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.868
MDCK Permeability:	3.774177093873732e-05
Pgp-inhibitor:	0.935
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.354
30% Bioavailability (F30%):	0.669

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.386
Plasma Protein Binding (PPB):	88.96187591552734%
Volume Distribution (VD):	0.558
Pgp-substrate:	4.564701557159424%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.624
CYP2C19-inhibitor:	0.179
CYP2C19-substrate:	0.838
CYP2C9-inhibitor:	0.358
CYP2C9-substrate:	0.478
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.212
CYP3A4-inhibitor:	0.603
CYP3A4-substrate:	0.335

ADMET: Excretion

Clearance (CL):	6.52
Half-life (T1/2):	0.289

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.261
Drug-inuced Liver Injury (DILI):	0.506
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.187
Skin Sensitization:	0.475
Carcinogencity:	0.044
Eye Corrosion:	0.006
Eye Irritation:	0.043
Respiratory Toxicity:	0.102

Download Data

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

Natural Product: NPC473424

Natural Product ID:	NPC473424
*Common Name:**	Hyousterone A
IUPAC Name:	(2R,3S,9R,10R,13R,14S,17R)-2,3,14-trihydroxy-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,9,11,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms:
Standard InCHIKey:	HRSCYVHZLUCLNT-YQCUPPGQSA-N
Standard InCHI:	InChI=1S/C27H42O5/c1-16(7-6-10-24(2,3)31)17-9-12-27(32)19-13-21(28)20-14-22(29)23(30)15-25(20,4)18(19)8-11-26(17,27)5/h13-14,16-18,22-23,29-32H,6-12,15H2,1-5H3/t16-,17-,18+,22+,23-,25-,26-,27-/m1/s1
SMILES:	O[C@@H]1C[C@@]2(C)C(=C[C@@H]1O)C(=O)C=C1[C@@H]2CC[C@]2([C@@]1(O)CC[C@@H]2[C@@H](CCCC(O)(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL428060
PubChem CID:	24762990
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols and derivatives

*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
NPO17267	Synoicum adareanum	Species	Polyclinidae	Eukaryota	n.a.	Antarctic	n.a.	PMID[18039009]
NPO17267	Synoicum adareanum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21737286]
NPO17267	Synoicum adareanum	Species	Polyclinidae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	10700.0	nM	PMID[468066]

☑ 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 NPC473424 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	187
0.1-0.2	1178
0.2-0.3	4440
0.3-0.4	10583
0.4-0.5	11418
0.5-0.6	7243
0.6-0.7	5488
0.7-0.8	1814
0.8-0.85	246
0.85-0.9	93
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9381	High Similarity	NPC477915
0.93	High Similarity	NPC65941
0.9293	High Similarity	NPC149047
0.9263	High Similarity	NPC249954
0.9208	High Similarity	NPC214644
0.92	High Similarity	NPC220229
0.92	High Similarity	NPC475060
0.9192	High Similarity	NPC209502
0.9192	High Similarity	NPC204833
0.9158	High Similarity	NPC259286
0.9158	High Similarity	NPC472932
0.9149	High Similarity	NPC69454
0.9109	High Similarity	NPC217201
0.91	High Similarity	NPC85829
0.91	High Similarity	NPC48733
0.91	High Similarity	NPC319077
0.91	High Similarity	NPC50692
0.91	High Similarity	NPC171137
0.91	High Similarity	NPC296945
0.91	High Similarity	NPC202167
0.91	High Similarity	NPC260268
0.91	High Similarity	NPC150531
0.91	High Similarity	NPC49958
0.91	High Similarity	NPC302607
0.91	High Similarity	NPC152695
0.91	High Similarity	NPC476027
0.91	High Similarity	NPC97202
0.91	High Similarity	NPC214264
0.9072	High Similarity	NPC197386
0.9062	High Similarity	NPC471463
0.9062	High Similarity	NPC117133
0.9053	High Similarity	NPC472976
0.9053	High Similarity	NPC472977
0.9043	High Similarity	NPC63748
0.902	High Similarity	NPC11710
0.901	High Similarity	NPC477916
0.901	High Similarity	NPC83744
0.8947	High Similarity	NPC472930
0.8922	High Similarity	NPC329417
0.8911	High Similarity	NPC323834
0.89	High Similarity	NPC311612
0.89	High Similarity	NPC111323
0.883	High Similarity	NPC275740
0.883	High Similarity	NPC86319
0.8824	High Similarity	NPC185
0.88	High Similarity	NPC195290
0.88	High Similarity	NPC204450
0.88	High Similarity	NPC87351
0.8788	High Similarity	NPC316964
0.8788	High Similarity	NPC154072
0.8776	High Similarity	NPC161147
0.8763	High Similarity	NPC200702
0.8763	High Similarity	NPC473170
0.8763	High Similarity	NPC318282
0.8763	High Similarity	NPC173875
0.8763	High Similarity	NPC469995
0.8763	High Similarity	NPC174948
0.875	High Similarity	NPC76084
0.875	High Similarity	NPC474736
0.875	High Similarity	NPC109305
0.8737	High Similarity	NPC48010
0.8723	High Similarity	NPC143767
0.8723	High Similarity	NPC471722
0.8723	High Similarity	NPC131470
0.8713	High Similarity	NPC236390
0.87	High Similarity	NPC302537
0.87	High Similarity	NPC163372
0.8687	High Similarity	NPC166745
0.8687	High Similarity	NPC235464
0.8679	High Similarity	NPC108721
0.8679	High Similarity	NPC73300
0.8673	High Similarity	NPC328371
0.866	High Similarity	NPC8993
0.866	High Similarity	NPC166906
0.8646	High Similarity	NPC233116
0.8646	High Similarity	NPC475806
0.8646	High Similarity	NPC473998
0.8646	High Similarity	NPC472978
0.8641	High Similarity	NPC472925
0.8632	High Similarity	NPC472973
0.8632	High Similarity	NPC32830
0.8632	High Similarity	NPC123912
0.8632	High Similarity	NPC473999
0.8632	High Similarity	NPC309603
0.8627	High Similarity	NPC149124
0.8627	High Similarity	NPC75531
0.8614	High Similarity	NPC119601
0.8614	High Similarity	NPC308726
0.8611	High Similarity	NPC471854
0.86	High Similarity	NPC110149
0.86	High Similarity	NPC144956
0.86	High Similarity	NPC287833
0.8586	High Similarity	NPC18319
0.8586	High Similarity	NPC18509
0.8586	High Similarity	NPC320306
0.8586	High Similarity	NPC474785
0.8586	High Similarity	NPC474938
0.8585	High Similarity	NPC207251
0.8571	High Similarity	NPC317586
0.8571	High Similarity	NPC470016
0.8571	High Similarity	NPC271195
0.8558	High Similarity	NPC177064
0.8558	High Similarity	NPC295244
0.8557	High Similarity	NPC472942
0.8544	High Similarity	NPC60681
0.8544	High Similarity	NPC257353
0.8542	High Similarity	NPC69622
0.8542	High Similarity	NPC191684
0.8542	High Similarity	NPC183283
0.8529	High Similarity	NPC26478
0.8529	High Similarity	NPC191892
0.8529	High Similarity	NPC55872
0.8526	High Similarity	NPC328539
0.8515	High Similarity	NPC472924
0.8511	High Similarity	NPC72133
0.8511	High Similarity	NPC472974
0.8505	High Similarity	NPC962
0.8505	High Similarity	NPC250109
0.8505	High Similarity	NPC317210
0.85	High Similarity	NPC471717
0.85	High Similarity	NPC10364
0.8485	Intermediate Similarity	NPC472941
0.8485	Intermediate Similarity	NPC305483
0.8485	Intermediate Similarity	NPC456
0.8485	Intermediate Similarity	NPC95565
0.8485	Intermediate Similarity	NPC96859
0.8485	Intermediate Similarity	NPC328162
0.8485	Intermediate Similarity	NPC173272
0.8469	Intermediate Similarity	NPC111015
0.8469	Intermediate Similarity	NPC299100
0.8469	Intermediate Similarity	NPC196227
0.8462	Intermediate Similarity	NPC144459
0.8454	Intermediate Similarity	NPC116726
0.8454	Intermediate Similarity	NPC168027
0.8454	Intermediate Similarity	NPC185936
0.8447	Intermediate Similarity	NPC28656
0.8438	Intermediate Similarity	NPC2983
0.8438	Intermediate Similarity	NPC477943
0.8438	Intermediate Similarity	NPC472970
0.8438	Intermediate Similarity	NPC1015
0.8438	Intermediate Similarity	NPC31985
0.8438	Intermediate Similarity	NPC472971
0.8431	Intermediate Similarity	NPC136289
0.8431	Intermediate Similarity	NPC293753
0.8431	Intermediate Similarity	NPC185530
0.8426	Intermediate Similarity	NPC326542
0.8421	Intermediate Similarity	NPC475740
0.8421	Intermediate Similarity	NPC138756
0.8416	Intermediate Similarity	NPC476274
0.8416	Intermediate Similarity	NPC51370
0.8416	Intermediate Similarity	NPC327431
0.8416	Intermediate Similarity	NPC205899
0.8416	Intermediate Similarity	NPC474720
0.8404	Intermediate Similarity	NPC474083
0.84	Intermediate Similarity	NPC190554
0.8396	Intermediate Similarity	NPC37116
0.8384	Intermediate Similarity	NPC180950
0.8384	Intermediate Similarity	NPC48330
0.8367	Intermediate Similarity	NPC250575
0.8364	Intermediate Similarity	NPC257457
0.8364	Intermediate Similarity	NPC311554
0.8364	Intermediate Similarity	NPC329736
0.8351	Intermediate Similarity	NPC136801
0.8351	Intermediate Similarity	NPC469400
0.8351	Intermediate Similarity	NPC320026
0.835	Intermediate Similarity	NPC249187
0.835	Intermediate Similarity	NPC247957
0.8349	Intermediate Similarity	NPC190286
0.8349	Intermediate Similarity	NPC266728
0.8349	Intermediate Similarity	NPC49492
0.8333	Intermediate Similarity	NPC476897
0.8333	Intermediate Similarity	NPC81530
0.8333	Intermediate Similarity	NPC224720
0.8333	Intermediate Similarity	NPC476240
0.8333	Intermediate Similarity	NPC471724
0.8333	Intermediate Similarity	NPC99411
0.8333	Intermediate Similarity	NPC476223
0.8318	Intermediate Similarity	NPC472928
0.8317	Intermediate Similarity	NPC186810
0.8317	Intermediate Similarity	NPC48647
0.8317	Intermediate Similarity	NPC147954
0.8317	Intermediate Similarity	NPC103051
0.8317	Intermediate Similarity	NPC114274
0.8316	Intermediate Similarity	NPC145879
0.8316	Intermediate Similarity	NPC475022
0.8316	Intermediate Similarity	NPC31564
0.8316	Intermediate Similarity	NPC469994
0.8316	Intermediate Similarity	NPC222613
0.8316	Intermediate Similarity	NPC474733
0.8316	Intermediate Similarity	NPC118648
0.8316	Intermediate Similarity	NPC474732
0.8316	Intermediate Similarity	NPC474778
0.8304	Intermediate Similarity	NPC46570
0.8298	Intermediate Similarity	NPC473246
0.8288	Intermediate Similarity	NPC61520
0.8288	Intermediate Similarity	NPC475041
0.8286	Intermediate Similarity	NPC165873
0.8286	Intermediate Similarity	NPC58370
0.8286	Intermediate Similarity	NPC43285
0.8283	Intermediate Similarity	NPC473162

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 NPC473424 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1517
0.2-0.3	3944
0.3-0.4	2404
0.4-0.5	647
0.5-0.6	167
0.6-0.7	153
0.7-0.8	135
0.8-0.85	26
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.88	High Similarity	NPD5211	Phase 2
0.8646	High Similarity	NPD6079	Approved
0.8632	High Similarity	NPD5328	Approved
0.8627	High Similarity	NPD5141	Approved
0.86	High Similarity	NPD5286	Approved
0.86	High Similarity	NPD4696	Approved
0.86	High Similarity	NPD5285	Approved
0.8586	High Similarity	NPD4755	Approved
0.8515	High Similarity	NPD5223	Approved
0.8431	Intermediate Similarity	NPD5226	Approved
0.8431	Intermediate Similarity	NPD5224	Approved
0.8431	Intermediate Similarity	NPD5225	Approved
0.8431	Intermediate Similarity	NPD4633	Approved
0.8416	Intermediate Similarity	NPD4700	Approved
0.8367	Intermediate Similarity	NPD4202	Approved
0.835	Intermediate Similarity	NPD5175	Approved
0.835	Intermediate Similarity	NPD5174	Approved
0.83	Intermediate Similarity	NPD5222	Approved
0.83	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.83	Intermediate Similarity	NPD5221	Approved
0.8224	Intermediate Similarity	NPD4634	Approved
0.8218	Intermediate Similarity	NPD5173	Approved
0.8208	Intermediate Similarity	NPD6881	Approved
0.8208	Intermediate Similarity	NPD6899	Approved
0.819	Intermediate Similarity	NPD6402	Approved
0.819	Intermediate Similarity	NPD7128	Approved
0.819	Intermediate Similarity	NPD6675	Approved
0.819	Intermediate Similarity	NPD5739	Approved
0.8173	Intermediate Similarity	NPD4754	Approved
0.8125	Intermediate Similarity	NPD3618	Phase 1
0.8119	Intermediate Similarity	NPD4697	Phase 3
0.8113	Intermediate Similarity	NPD5697	Approved
0.8105	Intermediate Similarity	NPD3665	Phase 1
0.8105	Intermediate Similarity	NPD4786	Approved
0.8105	Intermediate Similarity	NPD3666	Approved
0.8105	Intermediate Similarity	NPD3133	Approved
0.8073	Intermediate Similarity	NPD8297	Approved
0.8061	Intermediate Similarity	NPD4753	Phase 2
0.8056	Intermediate Similarity	NPD7290	Approved
0.8056	Intermediate Similarity	NPD6883	Approved
0.8056	Intermediate Similarity	NPD7102	Approved
0.8037	Intermediate Similarity	NPD5128	Approved
0.8037	Intermediate Similarity	NPD7320	Approved
0.8037	Intermediate Similarity	NPD4730	Approved
0.8037	Intermediate Similarity	NPD4729	Approved
0.8037	Intermediate Similarity	NPD6011	Approved
0.8019	Intermediate Similarity	NPD4767	Approved
0.8019	Intermediate Similarity	NPD4768	Approved
0.8	Intermediate Similarity	NPD4632	Approved
0.7982	Intermediate Similarity	NPD6649	Approved
0.7982	Intermediate Similarity	NPD6617	Approved
0.7982	Intermediate Similarity	NPD8130	Phase 1
0.7982	Intermediate Similarity	NPD6847	Approved
0.7982	Intermediate Similarity	NPD6650	Approved
0.7982	Intermediate Similarity	NPD6869	Approved
0.7963	Intermediate Similarity	NPD6014	Approved
0.7963	Intermediate Similarity	NPD6013	Approved
0.7963	Intermediate Similarity	NPD6012	Approved
0.7963	Intermediate Similarity	NPD6372	Approved
0.7963	Intermediate Similarity	NPD6373	Approved
0.7946	Intermediate Similarity	NPD7115	Discovery
0.7944	Intermediate Similarity	NPD5701	Approved
0.7938	Intermediate Similarity	NPD5690	Phase 2
0.7909	Intermediate Similarity	NPD6882	Approved
0.7895	Intermediate Similarity	NPD3667	Approved
0.7895	Intermediate Similarity	NPD4223	Phase 3
0.7895	Intermediate Similarity	NPD4221	Approved
0.789	Intermediate Similarity	NPD5249	Phase 3
0.789	Intermediate Similarity	NPD5251	Approved
0.789	Intermediate Similarity	NPD5247	Approved
0.789	Intermediate Similarity	NPD5248	Approved
0.789	Intermediate Similarity	NPD5250	Approved
0.789	Intermediate Similarity	NPD5135	Approved
0.789	Intermediate Similarity	NPD5169	Approved
0.789	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD4629	Approved
0.7843	Intermediate Similarity	NPD5210	Approved
0.7835	Intermediate Similarity	NPD5329	Approved
0.7818	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5127	Approved
0.7818	Intermediate Similarity	NPD5215	Approved
0.7818	Intermediate Similarity	NPD5217	Approved
0.7818	Intermediate Similarity	NPD5216	Approved
0.7755	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5280	Approved
0.7755	Intermediate Similarity	NPD5279	Phase 3
0.7755	Intermediate Similarity	NPD4694	Approved
0.7732	Intermediate Similarity	NPD4197	Approved
0.7692	Intermediate Similarity	NPD6083	Phase 2
0.7692	Intermediate Similarity	NPD6084	Phase 2
0.767	Intermediate Similarity	NPD5695	Phase 3
0.7632	Intermediate Similarity	NPD6009	Approved
0.7629	Intermediate Similarity	NPD4788	Approved
0.7611	Intermediate Similarity	NPD5167	Approved
0.7586	Intermediate Similarity	NPD6054	Approved
0.7586	Intermediate Similarity	NPD6319	Approved
0.7576	Intermediate Similarity	NPD4693	Phase 3
0.7576	Intermediate Similarity	NPD5205	Approved
0.7576	Intermediate Similarity	NPD4138	Approved
0.7576	Intermediate Similarity	NPD4688	Approved
0.7576	Intermediate Similarity	NPD4690	Approved
0.7576	Intermediate Similarity	NPD4689	Approved
0.7565	Intermediate Similarity	NPD6335	Approved
0.7549	Intermediate Similarity	NPD5284	Approved
0.7549	Intermediate Similarity	NPD7515	Phase 2
0.7549	Intermediate Similarity	NPD5281	Approved
0.7547	Intermediate Similarity	NPD7640	Approved
0.7547	Intermediate Similarity	NPD7639	Approved
0.7545	Intermediate Similarity	NPD5168	Approved
0.7544	Intermediate Similarity	NPD6274	Approved
0.7523	Intermediate Similarity	NPD6008	Approved
0.75	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD7101	Approved
0.7478	Intermediate Similarity	NPD6317	Approved
0.7476	Intermediate Similarity	NPD6399	Phase 3
0.7458	Intermediate Similarity	NPD6370	Approved
0.7453	Intermediate Similarity	NPD7638	Approved
0.7436	Intermediate Similarity	NPD6059	Approved
0.7414	Intermediate Similarity	NPD6313	Approved
0.7414	Intermediate Similarity	NPD6314	Approved
0.74	Intermediate Similarity	NPD6684	Approved
0.74	Intermediate Similarity	NPD7334	Approved
0.74	Intermediate Similarity	NPD7146	Approved
0.74	Intermediate Similarity	NPD7521	Approved
0.74	Intermediate Similarity	NPD6409	Approved
0.74	Intermediate Similarity	NPD5330	Approved
0.7396	Intermediate Similarity	NPD4195	Approved
0.7395	Intermediate Similarity	NPD7604	Phase 2
0.7374	Intermediate Similarity	NPD3668	Phase 3
0.7373	Intermediate Similarity	NPD6015	Approved
0.7373	Intermediate Similarity	NPD6016	Approved
0.7373	Intermediate Similarity	NPD5983	Phase 2
0.7333	Intermediate Similarity	NPD7492	Approved
0.7333	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7525	Registered
0.7311	Intermediate Similarity	NPD5988	Approved
0.7297	Intermediate Similarity	NPD6412	Phase 2
0.729	Intermediate Similarity	NPD5696	Approved
0.7282	Intermediate Similarity	NPD4096	Approved
0.7273	Intermediate Similarity	NPD7507	Approved
0.7273	Intermediate Similarity	NPD6336	Discontinued
0.7273	Intermediate Similarity	NPD6616	Approved
0.7263	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6903	Approved
0.7255	Intermediate Similarity	NPD4518	Approved
0.7245	Intermediate Similarity	NPD4139	Approved
0.7245	Intermediate Similarity	NPD4692	Approved
0.7241	Intermediate Similarity	NPD6868	Approved
0.7238	Intermediate Similarity	NPD7748	Approved
0.7228	Intermediate Similarity	NPD4623	Approved
0.7228	Intermediate Similarity	NPD4519	Discontinued
0.7227	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD6908	Approved
0.7227	Intermediate Similarity	NPD6909	Approved
0.7213	Intermediate Similarity	NPD7078	Approved
0.7212	Intermediate Similarity	NPD6050	Approved
0.7184	Intermediate Similarity	NPD6080	Approved
0.7184	Intermediate Similarity	NPD6673	Approved
0.7184	Intermediate Similarity	NPD6904	Approved
0.7158	Intermediate Similarity	NPD7339	Approved
0.7158	Intermediate Similarity	NPD6942	Approved
0.7154	Intermediate Similarity	NPD7736	Approved
0.7143	Intermediate Similarity	NPD4748	Discontinued
0.7143	Intermediate Similarity	NPD4695	Discontinued
0.7143	Intermediate Similarity	NPD5133	Approved
0.713	Intermediate Similarity	NPD4225	Approved
0.713	Intermediate Similarity	NPD6053	Discontinued
0.7129	Intermediate Similarity	NPD1696	Phase 3
0.7129	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5363	Approved
0.7115	Intermediate Similarity	NPD5785	Approved
0.7115	Intermediate Similarity	NPD5692	Phase 3
0.7097	Intermediate Similarity	NPD7319	Approved
0.7087	Intermediate Similarity	NPD5737	Approved
0.7087	Intermediate Similarity	NPD6672	Approved
0.7073	Intermediate Similarity	NPD8293	Discontinued
0.7048	Intermediate Similarity	NPD5693	Phase 1
0.7048	Intermediate Similarity	NPD5694	Approved
0.7037	Intermediate Similarity	NPD7902	Approved
0.7016	Intermediate Similarity	NPD6033	Approved
0.699	Remote Similarity	NPD3573	Approved
0.6952	Remote Similarity	NPD5207	Approved
0.6939	Remote Similarity	NPD3617	Approved
0.6939	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5091	Approved
0.6937	Remote Similarity	NPD7632	Discontinued
0.6931	Remote Similarity	NPD5362	Discontinued
0.6923	Remote Similarity	NPD5208	Approved
0.6917	Remote Similarity	NPD4522	Approved
0.6916	Remote Similarity	NPD6001	Approved
0.6909	Remote Similarity	NPD6404	Discontinued
0.6907	Remote Similarity	NPD6933	Approved
0.6893	Remote Similarity	NPD5786	Approved
0.6893	Remote Similarity	NPD6098	Approved
0.6887	Remote Similarity	NPD6411	Approved
0.6875	Remote Similarity	NPD4785	Approved
0.6875	Remote Similarity	NPD4784	Approved
0.6875	Remote Similarity	NPD5733	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