NPASS Compound

Structure

NPC250592 OpenBabel07101719252D 32 35 0 0 1 0 0 0 0 0999 V2000 -6.4836 2.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7707 3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 3.9190 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 1.7321 -0.0000 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 0.8660 0.5000 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 -4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7926 3.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1235 4.1270 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 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 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4325 5.0780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -0.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 27 1 0 0 0 0 11 26 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 0 0 0 0 14 19 1 0 0 0 0 15 3 1 1 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 16 23 2 0 0 0 0 17 26 1 6 0 0 0 18 27 1 6 0 0 0 19 28 1 1 0 0 0 20 25 1 0 0 0 0 20 29 1 6 0 0 0 21 24 1 0 0 0 0 21 30 1 1 0 0 0 22 23 1 0 0 0 0 22 31 2 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 6 0 0 0 25 32 1 6 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.32
Volume:	480.0
LogP:	3.505
LogD:	3.652
LogS:	-4.206
# 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:	0.515
Synthetic Accessibility Score:	5.001
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:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.803
MDCK Permeability:	1.8939230358228087e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.925

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199
Plasma Protein Binding (PPB):	94.60346221923828%
Volume Distribution (VD):	0.437
Pgp-substrate:	2.145002603530884%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.22
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.818
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.339

ADMET: Excretion

Clearance (CL):	6.838
Half-life (T1/2):	0.291

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.303
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.145
Skin Sensitization:	0.297
Carcinogencity:	0.051
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC250592

Natural Product ID:	NPC250592
*Common Name:**	Certonardosterol Q7
IUPAC Name:	(3S,4R,5S,6S,9R,10R,13R,17R)-3,4,6-trihydroxy-17-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,16,17-dodecahydrocyclopenta[a]phenanthren-15-one
Synonyms:	Certonardosterol Q7
Standard InCHIKey:	GBPZDYRTHBIZMU-JDIZXNFVSA-N
Standard InCHI:	InChI=1S/C27H44O5/c1-14(2)19(28)7-6-15(3)18-13-22(31)23-16-12-21(30)24-25(32)20(29)9-11-26(24,4)17(16)8-10-27(18,23)5/h14-15,17-21,24-25,28-30,32H,6-13H2,1-5H3/t15-,17+,18-,19+,20+,21+,24+,25+,26-,27-/m1/s1
SMILES:	CC([C@H](CC[C@H]([C@H]1CC(=O)C2=C3[C@H](CC[C@]12C)[C@@]1(C)CC[C@@H]([C@@H]([C@@H]1[C@H](C3)O)O)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458912
PubChem CID:	21589767
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001110] Tetrahydroxy bile acids, alcohols 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
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444692]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662097]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104487]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497935]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	7.1	ug ml-1	PMID[536284]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	3.8	ug ml-1	PMID[536284]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	4.66	ug ml-1	PMID[536284]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	6.65	ug ml-1	PMID[536284]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	4.58	ug ml-1	PMID[536284]

☑ 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 NPC250592 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	194
0.1-0.2	1328
0.2-0.3	4934
0.3-0.4	12615
0.4-0.5	9786
0.5-0.6	5916
0.6-0.7	5611
0.7-0.8	2117
0.8-0.85	171
0.85-0.9	21
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC77263
0.9765	High Similarity	NPC155304
0.9518	High Similarity	NPC197823
0.8864	High Similarity	NPC1015
0.8864	High Similarity	NPC31985
0.8851	High Similarity	NPC241875
0.8851	High Similarity	NPC469317
0.8851	High Similarity	NPC469314
0.8851	High Similarity	NPC138756
0.8837	High Similarity	NPC470574
0.8791	High Similarity	NPC473170
0.8791	High Similarity	NPC200702
0.8652	High Similarity	NPC32830
0.8636	High Similarity	NPC475740
0.8571	High Similarity	NPC109305
0.8571	High Similarity	NPC475255
0.8556	High Similarity	NPC136801
0.8539	High Similarity	NPC471722
0.8539	High Similarity	NPC470417
0.8523	High Similarity	NPC474778
0.8523	High Similarity	NPC474733
0.8523	High Similarity	NPC145879
0.8523	High Similarity	NPC72133
0.8523	High Similarity	NPC31564
0.8523	High Similarity	NPC474732
0.8495	Intermediate Similarity	NPC473158
0.8478	Intermediate Similarity	NPC245972
0.8478	Intermediate Similarity	NPC111015
0.8478	Intermediate Similarity	NPC196485
0.8462	Intermediate Similarity	NPC473166
0.8462	Intermediate Similarity	NPC189520
0.8444	Intermediate Similarity	NPC469319
0.8444	Intermediate Similarity	NPC229871
0.8427	Intermediate Similarity	NPC90652
0.8427	Intermediate Similarity	NPC99909
0.8427	Intermediate Similarity	NPC58063
0.8421	Intermediate Similarity	NPC316964
0.8404	Intermediate Similarity	NPC474938
0.8404	Intermediate Similarity	NPC474785
0.8391	Intermediate Similarity	NPC86370
0.837	Intermediate Similarity	NPC198074
0.837	Intermediate Similarity	NPC274046
0.8352	Intermediate Similarity	NPC48010
0.8333	Intermediate Similarity	NPC143767
0.8333	Intermediate Similarity	NPC328539
0.8333	Intermediate Similarity	NPC230387
0.8333	Intermediate Similarity	NPC292491
0.8333	Intermediate Similarity	NPC131470
0.8333	Intermediate Similarity	NPC158778
0.8333	Intermediate Similarity	NPC310752
0.8315	Intermediate Similarity	NPC471737
0.8298	Intermediate Similarity	NPC471463
0.8295	Intermediate Similarity	NPC59453
0.8295	Intermediate Similarity	NPC214043
0.8295	Intermediate Similarity	NPC85774
0.8295	Intermediate Similarity	NPC221758
0.8283	Intermediate Similarity	NPC475060
0.8283	Intermediate Similarity	NPC83744
0.8283	Intermediate Similarity	NPC220229
0.828	Intermediate Similarity	NPC166906
0.828	Intermediate Similarity	NPC474690
0.828	Intermediate Similarity	NPC472976
0.828	Intermediate Similarity	NPC472977
0.8276	Intermediate Similarity	NPC212083
0.8276	Intermediate Similarity	NPC151519
0.8261	Intermediate Similarity	NPC272746
0.8261	Intermediate Similarity	NPC168027
0.8261	Intermediate Similarity	NPC473167
0.8261	Intermediate Similarity	NPC473998
0.8261	Intermediate Similarity	NPC185936
0.8247	Intermediate Similarity	NPC477915
0.8242	Intermediate Similarity	NPC26959
0.8242	Intermediate Similarity	NPC474704
0.8242	Intermediate Similarity	NPC119416
0.8242	Intermediate Similarity	NPC473999
0.8242	Intermediate Similarity	NPC309603
0.8242	Intermediate Similarity	NPC275740
0.8242	Intermediate Similarity	NPC268406
0.8242	Intermediate Similarity	NPC86319
0.8242	Intermediate Similarity	NPC474245
0.8242	Intermediate Similarity	NPC475921
0.8242	Intermediate Similarity	NPC186688
0.8229	Intermediate Similarity	NPC110149
0.8222	Intermediate Similarity	NPC141292
0.8222	Intermediate Similarity	NPC477926
0.8211	Intermediate Similarity	NPC108078
0.8211	Intermediate Similarity	NPC18509
0.8202	Intermediate Similarity	NPC469948
0.82	Intermediate Similarity	NPC329417
0.82	Intermediate Similarity	NPC217201
0.8191	Intermediate Similarity	NPC473415
0.8191	Intermediate Similarity	NPC180557
0.8191	Intermediate Similarity	NPC469329
0.8191	Intermediate Similarity	NPC37787
0.8191	Intermediate Similarity	NPC317586
0.8191	Intermediate Similarity	NPC30677
0.8191	Intermediate Similarity	NPC470016
0.8191	Intermediate Similarity	NPC32118
0.8182	Intermediate Similarity	NPC302607
0.8182	Intermediate Similarity	NPC202167
0.8182	Intermediate Similarity	NPC85829
0.8182	Intermediate Similarity	NPC319077
0.8182	Intermediate Similarity	NPC97202
0.8182	Intermediate Similarity	NPC49958
0.8182	Intermediate Similarity	NPC214264
0.8182	Intermediate Similarity	NPC260268
0.8182	Intermediate Similarity	NPC48733
0.8182	Intermediate Similarity	NPC476027
0.8182	Intermediate Similarity	NPC323834
0.8182	Intermediate Similarity	NPC150531
0.8182	Intermediate Similarity	NPC296945
0.8182	Intermediate Similarity	NPC171137
0.8182	Intermediate Similarity	NPC152695
0.8182	Intermediate Similarity	NPC50692
0.8182	Intermediate Similarity	NPC149047
0.8172	Intermediate Similarity	NPC12722
0.8172	Intermediate Similarity	NPC474736
0.8163	Intermediate Similarity	NPC264048
0.8163	Intermediate Similarity	NPC191892
0.8152	Intermediate Similarity	NPC191684
0.8152	Intermediate Similarity	NPC183283
0.8152	Intermediate Similarity	NPC126993
0.8152	Intermediate Similarity	NPC85173
0.8132	Intermediate Similarity	NPC471724
0.8132	Intermediate Similarity	NPC474677
0.8132	Intermediate Similarity	NPC53911
0.8132	Intermediate Similarity	NPC44181
0.8132	Intermediate Similarity	NPC242864
0.8119	Intermediate Similarity	NPC214644
0.8119	Intermediate Similarity	NPC11710
0.8111	Intermediate Similarity	NPC222613
0.8111	Intermediate Similarity	NPC118648
0.8111	Intermediate Similarity	NPC51014
0.8111	Intermediate Similarity	NPC475022
0.8111	Intermediate Similarity	NPC158393
0.8105	Intermediate Similarity	NPC328162
0.8105	Intermediate Similarity	NPC204961
0.8105	Intermediate Similarity	NPC173744
0.8105	Intermediate Similarity	NPC73004
0.8105	Intermediate Similarity	NPC305483
0.8105	Intermediate Similarity	NPC91439
0.8105	Intermediate Similarity	NPC117133
0.8105	Intermediate Similarity	NPC88847
0.8105	Intermediate Similarity	NPC95565
0.8105	Intermediate Similarity	NPC96859
0.81	Intermediate Similarity	NPC477916
0.809	Intermediate Similarity	NPC227064
0.809	Intermediate Similarity	NPC473246
0.809	Intermediate Similarity	NPC321187
0.809	Intermediate Similarity	NPC329043
0.809	Intermediate Similarity	NPC58841
0.809	Intermediate Similarity	NPC161423
0.809	Intermediate Similarity	NPC472265
0.8085	Intermediate Similarity	NPC145667
0.8085	Intermediate Similarity	NPC282395
0.8085	Intermediate Similarity	NPC473172
0.8085	Intermediate Similarity	NPC263548
0.8085	Intermediate Similarity	NPC318332
0.8085	Intermediate Similarity	NPC174051
0.8085	Intermediate Similarity	NPC67831
0.8085	Intermediate Similarity	NPC8993
0.8085	Intermediate Similarity	NPC299996
0.8085	Intermediate Similarity	NPC231063
0.8085	Intermediate Similarity	NPC20235
0.8085	Intermediate Similarity	NPC88116
0.8085	Intermediate Similarity	NPC240617
0.8085	Intermediate Similarity	NPC32407
0.8081	Intermediate Similarity	NPC204833
0.8081	Intermediate Similarity	NPC209502
0.8068	Intermediate Similarity	NPC48362
0.8065	Intermediate Similarity	NPC475806
0.8065	Intermediate Similarity	NPC73457
0.8065	Intermediate Similarity	NPC63748
0.8065	Intermediate Similarity	NPC131872
0.8065	Intermediate Similarity	NPC235704
0.8065	Intermediate Similarity	NPC472978
0.8065	Intermediate Similarity	NPC233116
0.8061	Intermediate Similarity	NPC473424
0.8046	Intermediate Similarity	NPC22403
0.8046	Intermediate Similarity	NPC2482
0.8043	Intermediate Similarity	NPC473100
0.8043	Intermediate Similarity	NPC477943
0.8043	Intermediate Similarity	NPC122116
0.8041	Intermediate Similarity	NPC154072
0.8041	Intermediate Similarity	NPC144956
0.8022	Intermediate Similarity	NPC142361
0.8022	Intermediate Similarity	NPC474684
0.8022	Intermediate Similarity	NPC472324
0.8021	Intermediate Similarity	NPC9613
0.8021	Intermediate Similarity	NPC253826
0.8021	Intermediate Similarity	NPC247139
0.8021	Intermediate Similarity	NPC170978
0.8021	Intermediate Similarity	NPC320306
0.8021	Intermediate Similarity	NPC190554
0.802	Intermediate Similarity	NPC65941
0.8	Intermediate Similarity	NPC472824
0.8	Intermediate Similarity	NPC166607
0.8	Intermediate Similarity	NPC180950
0.8	Intermediate Similarity	NPC53565
0.8	Intermediate Similarity	NPC271195

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 NPC250592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1746
0.2-0.3	3991
0.3-0.4	2253
0.4-0.5	538
0.5-0.6	159
0.6-0.7	151
0.7-0.8	123
0.8-0.85	22
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8523	High Similarity	NPD3618	Phase 1
0.8444	Intermediate Similarity	NPD5328	Approved
0.8295	Intermediate Similarity	NPD4786	Approved
0.8276	Intermediate Similarity	NPD3667	Approved
0.8261	Intermediate Similarity	NPD6079	Approved
0.8211	Intermediate Similarity	NPD4755	Approved
0.8172	Intermediate Similarity	NPD4202	Approved
0.809	Intermediate Similarity	NPD3666	Approved
0.809	Intermediate Similarity	NPD3133	Approved
0.809	Intermediate Similarity	NPD3665	Phase 1
0.8041	Intermediate Similarity	NPD5286	Approved
0.8041	Intermediate Similarity	NPD4700	Approved
0.8041	Intermediate Similarity	NPD4696	Approved
0.8041	Intermediate Similarity	NPD5285	Approved
0.7917	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4697	Phase 3
0.7917	Intermediate Similarity	NPD5221	Approved
0.7917	Intermediate Similarity	NPD5222	Approved
0.7879	Intermediate Similarity	NPD5225	Approved
0.7879	Intermediate Similarity	NPD5226	Approved
0.7879	Intermediate Similarity	NPD5211	Phase 2
0.7879	Intermediate Similarity	NPD4633	Approved
0.7879	Intermediate Similarity	NPD5224	Approved
0.7872	Intermediate Similarity	NPD7515	Phase 2
0.7849	Intermediate Similarity	NPD4753	Phase 2
0.7835	Intermediate Similarity	NPD5173	Approved
0.7822	Intermediate Similarity	NPD6675	Approved
0.7822	Intermediate Similarity	NPD6402	Approved
0.7822	Intermediate Similarity	NPD7128	Approved
0.7822	Intermediate Similarity	NPD5739	Approved
0.7816	Intermediate Similarity	NPD3617	Approved
0.78	Intermediate Similarity	NPD5175	Approved
0.78	Intermediate Similarity	NPD5174	Approved
0.7789	Intermediate Similarity	NPD6399	Phase 3
0.7778	Intermediate Similarity	NPD5223	Approved
0.7723	Intermediate Similarity	NPD5141	Approved
0.7717	Intermediate Similarity	NPD5279	Phase 3
0.7717	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4634	Approved
0.7692	Intermediate Similarity	NPD3668	Phase 3
0.767	Intermediate Similarity	NPD6881	Approved
0.767	Intermediate Similarity	NPD6899	Approved
0.767	Intermediate Similarity	NPD7320	Approved
0.7647	Intermediate Similarity	NPD4768	Approved
0.7647	Intermediate Similarity	NPD4767	Approved
0.7624	Intermediate Similarity	NPD4754	Approved
0.7596	Intermediate Similarity	NPD6372	Approved
0.7596	Intermediate Similarity	NPD6373	Approved
0.7573	Intermediate Similarity	NPD5697	Approved
0.7573	Intermediate Similarity	NPD5701	Approved
0.7573	Intermediate Similarity	NPD6412	Phase 2
0.7547	Intermediate Similarity	NPD8297	Approved
0.7526	Intermediate Similarity	NPD7748	Approved
0.7524	Intermediate Similarity	NPD7102	Approved
0.7524	Intermediate Similarity	NPD7290	Approved
0.7524	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD4730	Approved
0.75	Intermediate Similarity	NPD5128	Approved
0.75	Intermediate Similarity	NPD4729	Approved
0.7475	Intermediate Similarity	NPD6084	Phase 2
0.7475	Intermediate Similarity	NPD7902	Approved
0.7475	Intermediate Similarity	NPD6083	Phase 2
0.7473	Intermediate Similarity	NPD4221	Approved
0.7473	Intermediate Similarity	NPD4223	Phase 3
0.7453	Intermediate Similarity	NPD8130	Phase 1
0.7453	Intermediate Similarity	NPD6617	Approved
0.7453	Intermediate Similarity	NPD6650	Approved
0.7453	Intermediate Similarity	NPD6869	Approved
0.7453	Intermediate Similarity	NPD6649	Approved
0.7453	Intermediate Similarity	NPD6847	Approved
0.7449	Intermediate Similarity	NPD4629	Approved
0.7449	Intermediate Similarity	NPD5210	Approved
0.7444	Intermediate Similarity	NPD4695	Discontinued
0.7444	Intermediate Similarity	NPD7525	Registered
0.7431	Intermediate Similarity	NPD7115	Discovery
0.7429	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6012	Approved
0.7429	Intermediate Similarity	NPD6014	Approved
0.7429	Intermediate Similarity	NPD6013	Approved
0.7419	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5329	Approved
0.7383	Intermediate Similarity	NPD6882	Approved
0.7358	Intermediate Similarity	NPD5250	Approved
0.7358	Intermediate Similarity	NPD5249	Phase 3
0.7358	Intermediate Similarity	NPD5248	Approved
0.7358	Intermediate Similarity	NPD5251	Approved
0.7358	Intermediate Similarity	NPD5247	Approved
0.734	Intermediate Similarity	NPD6409	Approved
0.734	Intermediate Similarity	NPD6684	Approved
0.734	Intermediate Similarity	NPD7521	Approved
0.734	Intermediate Similarity	NPD5330	Approved
0.734	Intermediate Similarity	NPD7334	Approved
0.734	Intermediate Similarity	NPD7146	Approved
0.7333	Intermediate Similarity	NPD6011	Approved
0.7326	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4632	Approved
0.7312	Intermediate Similarity	NPD4197	Approved
0.7303	Intermediate Similarity	NPD6116	Phase 1
0.7294	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5215	Approved
0.729	Intermediate Similarity	NPD5216	Approved
0.729	Intermediate Similarity	NPD5217	Approved
0.7273	Intermediate Similarity	NPD6942	Approved
0.7273	Intermediate Similarity	NPD7339	Approved
0.7264	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7638	Approved
0.7204	Intermediate Similarity	NPD4788	Approved
0.7196	Intermediate Similarity	NPD5135	Approved
0.7196	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5169	Approved
0.7191	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6117	Approved
0.7188	Intermediate Similarity	NPD6903	Approved
0.7188	Intermediate Similarity	NPD5737	Approved
0.7188	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6672	Approved
0.7172	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7900	Approved
0.717	Intermediate Similarity	NPD5168	Approved
0.7158	Intermediate Similarity	NPD4693	Phase 3
0.7158	Intermediate Similarity	NPD4690	Approved
0.7158	Intermediate Similarity	NPD4138	Approved
0.7158	Intermediate Similarity	NPD5205	Approved
0.7158	Intermediate Similarity	NPD4688	Approved
0.7158	Intermediate Similarity	NPD4689	Approved
0.7157	Intermediate Similarity	NPD7640	Approved
0.7157	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.713	Intermediate Similarity	NPD5127	Approved
0.71	Intermediate Similarity	NPD5695	Phase 3
0.708	Intermediate Similarity	NPD6059	Approved
0.708	Intermediate Similarity	NPD6319	Approved
0.708	Intermediate Similarity	NPD6054	Approved
0.7079	Intermediate Similarity	NPD3703	Phase 2
0.7059	Intermediate Similarity	NPD4225	Approved
0.7059	Intermediate Similarity	NPD5696	Approved
0.7037	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6697	Approved
0.7033	Intermediate Similarity	NPD6115	Approved
0.7033	Intermediate Similarity	NPD6118	Approved
0.7033	Intermediate Similarity	NPD6114	Approved
0.7027	Intermediate Similarity	NPD6274	Approved
0.7019	Intermediate Similarity	NPD7632	Discontinued
0.7011	Intermediate Similarity	NPD4244	Approved
0.7011	Intermediate Similarity	NPD4245	Approved
0.7	Intermediate Similarity	NPD6933	Approved
0.6991	Remote Similarity	NPD7100	Approved
0.6991	Remote Similarity	NPD7101	Approved
0.6989	Remote Similarity	NPD4692	Approved
0.6989	Remote Similarity	NPD4139	Approved
0.6981	Remote Similarity	NPD6008	Approved
0.6979	Remote Similarity	NPD5280	Approved
0.6979	Remote Similarity	NPD5690	Phase 2
0.6979	Remote Similarity	NPD4694	Approved
0.697	Remote Similarity	NPD5281	Approved
0.697	Remote Similarity	NPD5284	Approved
0.6966	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6009	Approved
0.6957	Remote Similarity	NPD7645	Phase 2
0.6957	Remote Similarity	NPD6370	Approved
0.6939	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5167	Approved
0.6931	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6335	Approved
0.6897	Remote Similarity	NPD4137	Phase 3
0.6897	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3698	Phase 2
0.6882	Remote Similarity	NPD4748	Discontinued
0.6882	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6868	Approved
0.687	Remote Similarity	NPD6908	Approved
0.687	Remote Similarity	NPD6015	Approved
0.687	Remote Similarity	NPD6909	Approved
0.687	Remote Similarity	NPD6016	Approved
0.6852	Remote Similarity	NPD6686	Approved
0.6838	Remote Similarity	NPD7492	Approved
0.6824	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4691	Approved
0.6818	Remote Similarity	NPD4747	Approved
0.6818	Remote Similarity	NPD4789	Approved
0.6814	Remote Similarity	NPD6317	Approved
0.681	Remote Similarity	NPD5988	Approved
0.6804	Remote Similarity	NPD4623	Approved
0.6804	Remote Similarity	NPD4519	Discontinued
0.68	Remote Similarity	NPD6411	Approved
0.6782	Remote Similarity	NPD5360	Phase 3
0.6782	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6616	Approved
0.6778	Remote Similarity	NPD6926	Approved
0.6778	Remote Similarity	NPD6924	Approved
0.6774	Remote Similarity	NPD4195	Approved
0.6768	Remote Similarity	NPD6673	Approved
0.6768	Remote Similarity	NPD6080	Approved
0.6768	Remote Similarity	NPD6904	Approved
0.6759	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6314	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