NPASS Compound

Structure

CID63748 OpenBabel06191715402D 31 34 0 0 1 0 0 0 0 0999 V2000 -5.8142 2.0786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2757 2.9218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3020 4.6094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8922 3.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5343 2.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8405 3.7661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3532 2.9226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2220 1.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2217 0.4864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6879 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8441 -1.4630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6896 1.9492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3015 2.9221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8147 3.7659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3790 2.9229 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9752 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6882 -0.9747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3787 1.9488 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5338 0.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6888 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8450 1.4619 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6891 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8447 0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5340 1.4614 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5544 -1.4744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5547 -1.4759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0209 1.9622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 2 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 27 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 18 4 1 1 0 0 0 18 21 1 0 0 0 0 19 27 1 6 0 0 0 20 29 1 6 0 0 0 21 28 1 6 0 0 0 22 25 1 0 0 0 0 22 28 1 6 0 0 0 23 25 1 0 0 0 0 23 30 2 0 0 0 0 24 26 1 0 0 0 0 24 31 1 1 0 0 0 25 26 2 0 0 0 0 26 27 1 0 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.33
Volume:	477.08
LogP:	4.97
LogD:	5.328
LogS:	-5.082
# Rotatable Bonds:	5
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	4.786
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.816
MDCK Permeability:	2.1859039406990632e-05
Pgp-inhibitor:	0.063
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.761
30% Bioavailability (F30%):	0.261

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.835
Plasma Protein Binding (PPB):	92.5440444946289%
Volume Distribution (VD):	0.927
Pgp-substrate:	4.0265583992004395%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.565
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.945
CYP2C9-inhibitor:	0.245
CYP2C9-substrate:	0.167
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.71
CYP3A4-inhibitor:	0.627
CYP3A4-substrate:	0.582

ADMET: Excretion

Clearance (CL):	12.389
Half-life (T1/2):	0.147

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.472
Drug-inuced Liver Injury (DILI):	0.401
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.949
Maximum Recommended Daily Dose:	0.795
Skin Sensitization:	0.054
Carcinogencity:	0.032
Eye Corrosion:	0.022
Eye Irritation:	0.028
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC63748

Natural Product ID:	NPC63748
*Common Name:**	3Beta,11Alpha-Dihydroxyergosta-8,24(28)-Dien-7-One
IUPAC Name:	(3S,5R,10S,11R,13R,14R,17R)-3,11-dihydroxy-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-1,2,3,4,5,6,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
Synonyms:
Standard InCHIKey:	IWSQIMKLMWQADE-MOKAYLCWSA-N
Standard InCHI:	InChI=1S/C28H44O3/c1-16(2)17(3)7-8-18(4)21-9-10-22-25-23(30)14-19-13-20(29)11-12-27(19,5)26(25)24(31)15-28(21,22)6/h16,18-22,24,29,31H,3,7-15H2,1-2,4-6H3/t18-,19-,20+,21-,22+,24-,27+,28-/m1/s1
SMILES:	CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2C3=C([C@@H](C[C@]12C)O)[C@@]1(C)CC[C@@H](C[C@@H]1CC3=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1631980
PubChem CID:	50899855
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO3499	Macaranga conifera	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(02)00378-3]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170686]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16156520]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21043476]
NPO3499	Macaranga conifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21275386]
NPO3499	Macaranga conifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3499	Macaranga conifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4483	Ganonema farinosum	Species	Liagoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9378	Halocynthia aurantium	Species	Pyuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1779	Sargassum kjellmanianum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11051	Nicotiana cavicola	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3499	Macaranga conifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2271	Cassia reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28869	Neonectria obtusispora	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8684	Nymphaea ampla	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO370	Rhizophora apiculata	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19426	Diospyros ferrea	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6631	Elaeagnus glabra	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO155	Artemisia lanata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5288	Stomatanthes corumbensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	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
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	28.0	ug.mL-1	PMID[566121]

☑ 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 NPC63748 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	154
0.1-0.2	1129
0.2-0.3	4947
0.3-0.4	12772
0.4-0.5	10318
0.5-0.6	6784
0.6-0.7	4853
0.7-0.8	1408
0.8-0.85	223
0.85-0.9	84
0.9-0.95	21
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9884	High Similarity	NPC69454
0.9659	High Similarity	NPC259286
0.9647	High Similarity	NPC131470
0.9647	High Similarity	NPC143767
0.9551	High Similarity	NPC249954
0.954	High Similarity	NPC233116
0.9535	High Similarity	NPC275740
0.9535	High Similarity	NPC86319
0.9432	High Similarity	NPC472930
0.9425	High Similarity	NPC183283
0.9412	High Similarity	NPC72133
0.931	High Similarity	NPC473999
0.931	High Similarity	NPC309603
0.9222	High Similarity	NPC173875
0.9222	High Similarity	NPC469995
0.9222	High Similarity	NPC318282
0.9222	High Similarity	NPC174948
0.9205	High Similarity	NPC48010
0.9195	High Similarity	NPC471722
0.9195	High Similarity	NPC328539
0.9121	High Similarity	NPC328371
0.9111	High Similarity	NPC166906
0.9101	High Similarity	NPC475806
0.9101	High Similarity	NPC473998
0.907	High Similarity	NPC474083
0.9043	High Similarity	NPC473424
0.9022	High Similarity	NPC320306
0.9011	High Similarity	NPC472932
0.9011	High Similarity	NPC271195
0.9011	High Similarity	NPC470016
0.9011	High Similarity	NPC317586
0.8989	High Similarity	NPC191684
0.8977	High Similarity	NPC471724
0.8953	High Similarity	NPC473246
0.8936	High Similarity	NPC163372
0.8936	High Similarity	NPC302537
0.8913	High Similarity	NPC305483
0.8913	High Similarity	NPC96859
0.8913	High Similarity	NPC328162
0.8901	High Similarity	NPC184870
0.8901	High Similarity	NPC8993
0.8889	High Similarity	NPC168027
0.8889	High Similarity	NPC185936
0.8876	High Similarity	NPC472973
0.8876	High Similarity	NPC214387
0.8876	High Similarity	NPC123912
0.8864	High Similarity	NPC475740
0.8851	High Similarity	NPC470574
0.8851	High Similarity	NPC471224
0.8842	High Similarity	NPC119601
0.8842	High Similarity	NPC308726
0.8842	High Similarity	NPC477915
0.883	High Similarity	NPC51370
0.883	High Similarity	NPC287833
0.883	High Similarity	NPC327431
0.8804	High Similarity	NPC37646
0.8804	High Similarity	NPC297199
0.8778	High Similarity	NPC477149
0.8778	High Similarity	NPC469400
0.8778	High Similarity	NPC477147
0.8763	High Similarity	NPC323834
0.875	High Similarity	NPC145879
0.875	High Similarity	NPC222613
0.875	High Similarity	NPC94755
0.875	High Similarity	NPC474732
0.875	High Similarity	NPC474778
0.875	High Similarity	NPC475022
0.875	High Similarity	NPC118648
0.875	High Similarity	NPC31564
0.875	High Similarity	NPC474733
0.875	High Similarity	NPC55309
0.875	High Similarity	NPC28252
0.8737	High Similarity	NPC472924
0.8736	High Similarity	NPC85774
0.8736	High Similarity	NPC214043
0.8723	High Similarity	NPC103051
0.8723	High Similarity	NPC471717
0.8723	High Similarity	NPC197386
0.871	High Similarity	NPC243525
0.871	High Similarity	NPC3772
0.871	High Similarity	NPC472941
0.871	High Similarity	NPC40765
0.871	High Similarity	NPC117133
0.871	High Similarity	NPC7124
0.871	High Similarity	NPC456
0.8696	High Similarity	NPC469406
0.8681	High Similarity	NPC107690
0.8681	High Similarity	NPC272746
0.8681	High Similarity	NPC472978
0.8673	High Similarity	NPC472925
0.8667	High Similarity	NPC31985
0.8667	High Similarity	NPC1015
0.8667	High Similarity	NPC472971
0.8667	High Similarity	NPC472970
0.8667	High Similarity	NPC186688
0.866	High Similarity	NPC204833
0.866	High Similarity	NPC209502
0.8652	High Similarity	NPC58063
0.8652	High Similarity	NPC187376
0.8652	High Similarity	NPC159046
0.8652	High Similarity	NPC233836
0.8652	High Similarity	NPC4643
0.8646	High Similarity	NPC234892
0.8646	High Similarity	NPC204450
0.8646	High Similarity	NPC293753
0.8646	High Similarity	NPC195290
0.8636	High Similarity	NPC469948
0.8632	High Similarity	NPC154072
0.8632	High Similarity	NPC476274
0.8632	High Similarity	NPC316964
0.8621	High Similarity	NPC476082
0.8621	High Similarity	NPC278648
0.8617	High Similarity	NPC121339
0.8617	High Similarity	NPC18319
0.8617	High Similarity	NPC106557
0.8617	High Similarity	NPC122294
0.8617	High Similarity	NPC43747
0.8617	High Similarity	NPC161147
0.8602	High Similarity	NPC200702
0.8602	High Similarity	NPC255809
0.8587	High Similarity	NPC477520
0.8587	High Similarity	NPC474736
0.8587	High Similarity	NPC109305
0.8587	High Similarity	NPC470254
0.8587	High Similarity	NPC475255
0.8586	High Similarity	NPC295244
0.8571	High Similarity	NPC319077
0.8571	High Similarity	NPC97202
0.8571	High Similarity	NPC296945
0.8571	High Similarity	NPC49958
0.8571	High Similarity	NPC302607
0.8571	High Similarity	NPC202167
0.8571	High Similarity	NPC126993
0.8571	High Similarity	NPC214264
0.8571	High Similarity	NPC150531
0.8571	High Similarity	NPC85173
0.8571	High Similarity	NPC149047
0.8571	High Similarity	NPC171137
0.8571	High Similarity	NPC152695
0.8571	High Similarity	NPC50692
0.8571	High Similarity	NPC260268
0.8571	High Similarity	NPC476027
0.8571	High Similarity	NPC48733
0.8571	High Similarity	NPC85829
0.8571	High Similarity	NPC69622
0.8557	High Similarity	NPC236390
0.8557	High Similarity	NPC55872
0.8557	High Similarity	NPC251017
0.8556	High Similarity	NPC53911
0.8556	High Similarity	NPC242864
0.8542	High Similarity	NPC476223
0.8542	High Similarity	NPC476240
0.8542	High Similarity	NPC224720
0.8539	High Similarity	NPC469994
0.8539	High Similarity	NPC472985
0.8539	High Similarity	NPC472986
0.8539	High Similarity	NPC472974
0.8526	High Similarity	NPC10364
0.8526	High Similarity	NPC16021
0.8523	High Similarity	NPC59453
0.8523	High Similarity	NPC227132
0.8523	High Similarity	NPC221758
0.8511	High Similarity	NPC471463
0.8511	High Similarity	NPC95565
0.8511	High Similarity	NPC192428
0.8495	Intermediate Similarity	NPC472976
0.8495	Intermediate Similarity	NPC299100
0.8495	Intermediate Similarity	NPC474690
0.8495	Intermediate Similarity	NPC196485
0.8495	Intermediate Similarity	NPC111015
0.8495	Intermediate Similarity	NPC472977
0.8495	Intermediate Similarity	NPC245972
0.8488	Intermediate Similarity	NPC164999
0.8485	Intermediate Similarity	NPC475060
0.8485	Intermediate Similarity	NPC83744
0.8485	Intermediate Similarity	NPC220229
0.8485	Intermediate Similarity	NPC477916
0.8478	Intermediate Similarity	NPC472975
0.8478	Intermediate Similarity	NPC212948
0.8469	Intermediate Similarity	NPC28656
0.8462	Intermediate Similarity	NPC477943
0.8462	Intermediate Similarity	NPC472240
0.8462	Intermediate Similarity	NPC472983
0.8462	Intermediate Similarity	NPC119416
0.8462	Intermediate Similarity	NPC268406
0.8462	Intermediate Similarity	NPC26959
0.8462	Intermediate Similarity	NPC84271
0.8462	Intermediate Similarity	NPC2983
0.8462	Intermediate Similarity	NPC77168
0.8462	Intermediate Similarity	NPC102414
0.8462	Intermediate Similarity	NPC262858
0.8454	Intermediate Similarity	NPC136289
0.8444	Intermediate Similarity	NPC141292
0.8444	Intermediate Similarity	NPC474684
0.8444	Intermediate Similarity	NPC138756
0.8444	Intermediate Similarity	NPC142361
0.8444	Intermediate Similarity	NPC136548
0.8444	Intermediate Similarity	NPC287079
0.8438	Intermediate Similarity	NPC144660
0.8438	Intermediate Similarity	NPC299971

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 NPC63748 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1529
0.2-0.3	4101
0.3-0.4	2358
0.4-0.5	556
0.5-0.6	161
0.6-0.7	173
0.7-0.8	113
0.8-0.85	14
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.931	High Similarity	NPD5328	Approved
0.9101	High Similarity	NPD6079	Approved
0.875	High Similarity	NPD3618	Phase 1
0.8523	High Similarity	NPD4786	Approved
0.8511	High Similarity	NPD5220	Clinical (unspecified phase)
0.8511	High Similarity	NPD5222	Approved
0.8511	High Similarity	NPD5221	Approved
0.8511	High Similarity	NPD4697	Phase 3
0.8454	Intermediate Similarity	NPD5211	Phase 2
0.8421	Intermediate Similarity	NPD5173	Approved
0.8421	Intermediate Similarity	NPD4755	Approved
0.8387	Intermediate Similarity	NPD4202	Approved
0.8333	Intermediate Similarity	NPD5279	Phase 3
0.8315	Intermediate Similarity	NPD3666	Approved
0.8315	Intermediate Similarity	NPD3133	Approved
0.8315	Intermediate Similarity	NPD3665	Phase 1
0.8295	Intermediate Similarity	NPD3667	Approved
0.8283	Intermediate Similarity	NPD5141	Approved
0.8247	Intermediate Similarity	NPD5286	Approved
0.8247	Intermediate Similarity	NPD5285	Approved
0.8247	Intermediate Similarity	NPD4700	Approved
0.8247	Intermediate Similarity	NPD4696	Approved
0.8163	Intermediate Similarity	NPD5223	Approved
0.8081	Intermediate Similarity	NPD4633	Approved
0.8081	Intermediate Similarity	NPD5224	Approved
0.8081	Intermediate Similarity	NPD5225	Approved
0.8081	Intermediate Similarity	NPD5226	Approved
0.802	Intermediate Similarity	NPD6675	Approved
0.802	Intermediate Similarity	NPD5739	Approved
0.802	Intermediate Similarity	NPD6402	Approved
0.802	Intermediate Similarity	NPD7128	Approved
0.8	Intermediate Similarity	NPD4754	Approved
0.8	Intermediate Similarity	NPD5174	Approved
0.8	Intermediate Similarity	NPD5175	Approved
0.7895	Intermediate Similarity	NPD7515	Phase 2
0.7889	Intermediate Similarity	NPD4223	Phase 3
0.7889	Intermediate Similarity	NPD4221	Approved
0.7872	Intermediate Similarity	NPD4753	Phase 2
0.7864	Intermediate Similarity	NPD6899	Approved
0.7864	Intermediate Similarity	NPD6881	Approved
0.7864	Intermediate Similarity	NPD7320	Approved
0.7843	Intermediate Similarity	NPD4767	Approved
0.7843	Intermediate Similarity	NPD4768	Approved
0.7826	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5329	Approved
0.7788	Intermediate Similarity	NPD6372	Approved
0.7788	Intermediate Similarity	NPD6373	Approved
0.7767	Intermediate Similarity	NPD5701	Approved
0.7767	Intermediate Similarity	NPD5697	Approved
0.7742	Intermediate Similarity	NPD5690	Phase 2
0.7742	Intermediate Similarity	NPD4694	Approved
0.7742	Intermediate Similarity	NPD5280	Approved
0.7717	Intermediate Similarity	NPD4197	Approved
0.7714	Intermediate Similarity	NPD6883	Approved
0.7714	Intermediate Similarity	NPD7102	Approved
0.7714	Intermediate Similarity	NPD7290	Approved
0.77	Intermediate Similarity	NPD7640	Approved
0.77	Intermediate Similarity	NPD7639	Approved
0.7692	Intermediate Similarity	NPD5168	Approved
0.7692	Intermediate Similarity	NPD4729	Approved
0.7692	Intermediate Similarity	NPD5128	Approved
0.7692	Intermediate Similarity	NPD6011	Approved
0.7692	Intermediate Similarity	NPD4730	Approved
0.7642	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD8130	Phase 1
0.7642	Intermediate Similarity	NPD6650	Approved
0.7642	Intermediate Similarity	NPD6617	Approved
0.7642	Intermediate Similarity	NPD6869	Approved
0.7642	Intermediate Similarity	NPD6847	Approved
0.7642	Intermediate Similarity	NPD6649	Approved
0.764	Intermediate Similarity	NPD3617	Approved
0.7629	Intermediate Similarity	NPD6399	Phase 3
0.7619	Intermediate Similarity	NPD6012	Approved
0.7619	Intermediate Similarity	NPD6013	Approved
0.7619	Intermediate Similarity	NPD6014	Approved
0.7609	Intermediate Similarity	NPD4788	Approved
0.76	Intermediate Similarity	NPD7638	Approved
0.757	Intermediate Similarity	NPD8297	Approved
0.757	Intermediate Similarity	NPD6882	Approved
0.7553	Intermediate Similarity	NPD4688	Approved
0.7553	Intermediate Similarity	NPD4138	Approved
0.7553	Intermediate Similarity	NPD6409	Approved
0.7553	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD4690	Approved
0.7553	Intermediate Similarity	NPD4689	Approved
0.7553	Intermediate Similarity	NPD6684	Approved
0.7553	Intermediate Similarity	NPD4623	Approved
0.7553	Intermediate Similarity	NPD7146	Approved
0.7553	Intermediate Similarity	NPD4693	Phase 3
0.7553	Intermediate Similarity	NPD4519	Discontinued
0.7553	Intermediate Similarity	NPD7521	Approved
0.7553	Intermediate Similarity	NPD7334	Approved
0.7553	Intermediate Similarity	NPD5205	Approved
0.7553	Intermediate Similarity	NPD5330	Approved
0.7551	Intermediate Similarity	NPD7748	Approved
0.7547	Intermediate Similarity	NPD5169	Approved
0.7547	Intermediate Similarity	NPD5250	Approved
0.7547	Intermediate Similarity	NPD5247	Approved
0.7547	Intermediate Similarity	NPD5248	Approved
0.7547	Intermediate Similarity	NPD5251	Approved
0.7547	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4634	Approved
0.7547	Intermediate Similarity	NPD5135	Approved
0.7547	Intermediate Similarity	NPD5249	Phase 3
0.7527	Intermediate Similarity	NPD3668	Phase 3
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD6942	Approved
0.75	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD7339	Approved
0.7477	Intermediate Similarity	NPD5217	Approved
0.7477	Intermediate Similarity	NPD5216	Approved
0.7477	Intermediate Similarity	NPD5215	Approved
0.7477	Intermediate Similarity	NPD5127	Approved
0.7475	Intermediate Similarity	NPD4629	Approved
0.7475	Intermediate Similarity	NPD5210	Approved
0.7475	Intermediate Similarity	NPD5695	Phase 3
0.7473	Intermediate Similarity	NPD7525	Registered
0.7455	Intermediate Similarity	NPD7115	Discovery
0.7396	Intermediate Similarity	NPD5737	Approved
0.7396	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6903	Approved
0.7396	Intermediate Similarity	NPD6672	Approved
0.7391	Intermediate Similarity	NPD4692	Approved
0.7391	Intermediate Similarity	NPD4139	Approved
0.7386	Intermediate Similarity	NPD5733	Approved
0.7364	Intermediate Similarity	NPD6868	Approved
0.7356	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5284	Approved
0.7347	Intermediate Similarity	NPD5281	Approved
0.7339	Intermediate Similarity	NPD4632	Approved
0.7327	Intermediate Similarity	NPD7902	Approved
0.7303	Intermediate Similarity	NPD3703	Phase 2
0.7273	Intermediate Similarity	NPD5167	Approved
0.7253	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD4096	Approved
0.7241	Intermediate Similarity	NPD4747	Approved
0.7232	Intermediate Similarity	NPD6335	Approved
0.7222	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7632	Discontinued
0.7207	Intermediate Similarity	NPD6274	Approved
0.7191	Intermediate Similarity	NPD4687	Approved
0.7184	Intermediate Similarity	NPD6404	Discontinued
0.7174	Intermediate Similarity	NPD4195	Approved
0.7172	Intermediate Similarity	NPD8035	Phase 2
0.7172	Intermediate Similarity	NPD8034	Phase 2
0.717	Intermediate Similarity	NPD6008	Approved
0.7168	Intermediate Similarity	NPD7100	Approved
0.7168	Intermediate Similarity	NPD7101	Approved
0.7159	Intermediate Similarity	NPD5276	Approved
0.7143	Intermediate Similarity	NPD6009	Approved
0.7143	Intermediate Similarity	NPD6317	Approved
0.7129	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4137	Phase 3
0.7126	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3573	Approved
0.7105	Intermediate Similarity	NPD6054	Approved
0.7105	Intermediate Similarity	NPD6059	Approved
0.71	Intermediate Similarity	NPD5133	Approved
0.7097	Intermediate Similarity	NPD4695	Discontinued
0.7097	Intermediate Similarity	NPD4748	Discontinued
0.7087	Intermediate Similarity	NPD5696	Approved
0.7083	Intermediate Similarity	NPD1696	Phase 3
0.708	Intermediate Similarity	NPD6314	Approved
0.708	Intermediate Similarity	NPD6313	Approved
0.7045	Intermediate Similarity	NPD4691	Approved
0.7043	Intermediate Similarity	NPD6908	Approved
0.7043	Intermediate Similarity	NPD6909	Approved
0.7041	Intermediate Similarity	NPD4518	Approved
0.7033	Intermediate Similarity	NPD6117	Approved
0.703	Intermediate Similarity	NPD7900	Approved
0.703	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6050	Approved
0.7	Intermediate Similarity	NPD6411	Approved
0.6989	Remote Similarity	NPD7645	Phase 2
0.6983	Remote Similarity	NPD6370	Approved
0.697	Remote Similarity	NPD6673	Approved
0.697	Remote Similarity	NPD6904	Approved
0.697	Remote Similarity	NPD6080	Approved
0.6957	Remote Similarity	NPD6116	Phase 1
0.6957	Remote Similarity	NPD6319	Approved
0.6944	Remote Similarity	NPD6412	Phase 2
0.6931	Remote Similarity	NPD5779	Approved
0.6931	Remote Similarity	NPD5778	Approved
0.6923	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD5290	Discontinued
0.6923	Remote Similarity	NPD8264	Approved
0.6915	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD1694	Approved
0.69	Remote Similarity	NPD5692	Phase 3
0.69	Remote Similarity	NPD5207	Approved
0.6897	Remote Similarity	NPD5983	Phase 2
0.6897	Remote Similarity	NPD6016	Approved
0.6897	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6015	Approved
0.6882	Remote Similarity	NPD6118	Approved
0.6882	Remote Similarity	NPD6115	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