NPASS Compound

Structure

NPC475664 OpenBabel07101718292D 31 34 0 0 1 0 0 0 0 0999 V2000 -6.7926 -3.3838 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 -5.1453 -3.9190 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 -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 -6.4325 -5.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1235 -4.1270 0.0000 C 0 0 3 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 2 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 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 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 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 -7.4106 -5.2859 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 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 26 1 0 0 0 0 10 25 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 15 2 1 6 0 0 0 15 18 1 0 0 0 0 16 11 1 6 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 25 1 1 0 0 0 18 26 1 1 0 0 0 19 24 1 0 0 0 0 19 28 1 1 0 0 0 20 23 1 0 0 0 0 20 29 1 6 0 0 0 21 22 1 0 0 0 0 21 30 1 1 0 0 0 22 26 1 1 0 0 0 23 24 1 0 0 0 0 23 25 1 1 0 0 0 24 31 1 1 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.32
Volume:	465.341
LogP:	3.495
LogD:	3.843
LogS:	-3.543
# Rotatable Bonds:	4
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	5.176
Fsp3:	0.923
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:	-5.136
MDCK Permeability:	9.064553887583315e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.942
20% Bioavailability (F20%):	0.819
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.243
Plasma Protein Binding (PPB):	85.4466781616211%
Volume Distribution (VD):	0.665
Pgp-substrate:	2.3017828464508057%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.341
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.75
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.255
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.08
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	1.2
Half-life (T1/2):	0.569

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.349
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.27
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.428
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC475664

Natural Product ID:	NPC475664
*Common Name:**	Certonardosterol B3
IUPAC Name:	(3S,4R,5S,6S,8R,9S,10R,13R,14S,15R,17R)-17-[(E,2R)-6-hydroxy-5-methylhex-3-en-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,4,6,15-tetrol
Synonyms:	Certonardosterol B3
Standard InCHIKey:	BHGXXPKHMZXFLF-MKIDYTFDSA-N
Standard InCHI:	InChI=1S/C26H44O5/c1-14(13-27)5-6-15(2)18-12-21(30)22-16-11-20(29)23-24(31)19(28)8-10-25(23,3)17(16)7-9-26(18,22)4/h5-6,14-24,27-31H,7-13H2,1-4H3/b6-5+/t14?,15-,16-,17+,18-,19+,20+,21-,22-,23+,24+,25-,26-/m1/s1
SMILES:	CC(CO)C=CC(C)C1CC(C2C1(CCC3C2CC(C4C3(CCC(C4O)O)C)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510934
PubChem CID:	21589768
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003027] 3-hydroxysteroids [CHEMONTID:0003233] 3-beta-hydroxysteroids

*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	=	10.4	ug ml-1	PMID[543700]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	14.7	ug ml-1	PMID[543700]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	7.13	ug ml-1	PMID[543700]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	12.1	ug ml-1	PMID[543700]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	12.5	ug ml-1	PMID[543700]

☑ 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 NPC475664 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	192
0.1-0.2	1527
0.2-0.3	5744
0.3-0.4	14983
0.4-0.5	8703
0.5-0.6	4984
0.6-0.7	4677
0.7-0.8	1671
0.8-0.85	158
0.85-0.9	37
0.9-0.95	13
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC474657
0.9878	High Similarity	NPC186145
0.9762	High Similarity	NPC475751
0.9762	High Similarity	NPC473956
0.9643	High Similarity	NPC109744
0.9512	High Similarity	NPC127606
0.9512	High Similarity	NPC475798
0.9412	High Similarity	NPC105495
0.939	High Similarity	NPC193870
0.939	High Similarity	NPC141941
0.9286	High Similarity	NPC6605
0.9277	High Similarity	NPC255882
0.9157	High Similarity	NPC110778
0.9157	High Similarity	NPC477818
0.9059	High Similarity	NPC139724
0.9059	High Similarity	NPC24277
0.9059	High Similarity	NPC201273
0.9059	High Similarity	NPC121981
0.9048	High Similarity	NPC124172
0.8929	High Similarity	NPC207013
0.8901	High Similarity	NPC477226
0.8837	High Similarity	NPC71520
0.8837	High Similarity	NPC269058
0.8824	High Similarity	NPC209802
0.881	High Similarity	NPC1272
0.881	High Similarity	NPC470614
0.8795	High Similarity	NPC78545
0.8795	High Similarity	NPC71535
0.8791	High Similarity	NPC471903
0.8764	High Similarity	NPC275671
0.8764	High Similarity	NPC41554
0.8764	High Similarity	NPC97404
0.8706	High Similarity	NPC211135
0.8706	High Similarity	NPC216420
0.8706	High Similarity	NPC232023
0.8706	High Similarity	NPC85095
0.869	High Similarity	NPC474531
0.8652	High Similarity	NPC11216
0.8652	High Similarity	NPC80561
0.8652	High Similarity	NPC329596
0.8652	High Similarity	NPC204188
0.8652	High Similarity	NPC291484
0.8652	High Similarity	NPC3345
0.8636	High Similarity	NPC133588
0.8636	High Similarity	NPC474668
0.8636	High Similarity	NPC67872
0.8636	High Similarity	NPC470542
0.8621	High Similarity	NPC237344
0.8621	High Similarity	NPC94462
0.8588	High Similarity	NPC30166
0.8571	High Similarity	NPC102253
0.8571	High Similarity	NPC26117
0.8571	High Similarity	NPC236237
0.8571	High Similarity	NPC236112
0.8571	High Similarity	NPC322313
0.8571	High Similarity	NPC13554
0.8571	High Similarity	NPC287749
0.8554	High Similarity	NPC477819
0.8554	High Similarity	NPC244385
0.8554	High Similarity	NPC6978
0.8554	High Similarity	NPC148977
0.8554	High Similarity	NPC477817
0.8554	High Similarity	NPC138621
0.8554	High Similarity	NPC167037
0.8539	High Similarity	NPC470361
0.8523	High Similarity	NPC470620
0.8511	High Similarity	NPC208358
0.8495	Intermediate Similarity	NPC476021
0.8495	Intermediate Similarity	NPC316604
0.8495	Intermediate Similarity	NPC474994
0.8495	Intermediate Similarity	NPC475032
0.8495	Intermediate Similarity	NPC475033
0.8495	Intermediate Similarity	NPC476040
0.8488	Intermediate Similarity	NPC113978
0.8471	Intermediate Similarity	NPC470383
0.8462	Intermediate Similarity	NPC98193
0.8452	Intermediate Similarity	NPC472463
0.8452	Intermediate Similarity	NPC1319
0.8452	Intermediate Similarity	NPC80530
0.8452	Intermediate Similarity	NPC273410
0.8444	Intermediate Similarity	NPC107189
0.8427	Intermediate Similarity	NPC2158
0.8421	Intermediate Similarity	NPC155974
0.8415	Intermediate Similarity	NPC103822
0.8409	Intermediate Similarity	NPC293287
0.8409	Intermediate Similarity	NPC152808
0.8409	Intermediate Similarity	NPC261266
0.8409	Intermediate Similarity	NPC299068
0.8409	Intermediate Similarity	NPC6391
0.8391	Intermediate Similarity	NPC469878
0.8391	Intermediate Similarity	NPC474493
0.8391	Intermediate Similarity	NPC256567
0.8391	Intermediate Similarity	NPC185568
0.8391	Intermediate Similarity	NPC238992
0.8387	Intermediate Similarity	NPC288970
0.8372	Intermediate Similarity	NPC248886
0.8372	Intermediate Similarity	NPC7988
0.837	Intermediate Similarity	NPC65402
0.837	Intermediate Similarity	NPC127718
0.8353	Intermediate Similarity	NPC47149
0.8352	Intermediate Similarity	NPC210268
0.8351	Intermediate Similarity	NPC312774
0.8333	Intermediate Similarity	NPC87604
0.8333	Intermediate Similarity	NPC285761
0.8333	Intermediate Similarity	NPC477522
0.8315	Intermediate Similarity	NPC271967
0.8313	Intermediate Similarity	NPC237460
0.8313	Intermediate Similarity	NPC163597
0.8298	Intermediate Similarity	NPC476893
0.8295	Intermediate Similarity	NPC318390
0.8295	Intermediate Similarity	NPC470360
0.828	Intermediate Similarity	NPC8774
0.8276	Intermediate Similarity	NPC253402
0.8276	Intermediate Similarity	NPC317458
0.8276	Intermediate Similarity	NPC159168
0.8261	Intermediate Similarity	NPC310013
0.8256	Intermediate Similarity	NPC157655
0.8235	Intermediate Similarity	NPC24504
0.8235	Intermediate Similarity	NPC328714
0.8235	Intermediate Similarity	NPC476316
0.8222	Intermediate Similarity	NPC212596
0.8222	Intermediate Similarity	NPC475605
0.8222	Intermediate Similarity	NPC4574
0.8214	Intermediate Similarity	NPC471798
0.8214	Intermediate Similarity	NPC105208
0.8214	Intermediate Similarity	NPC477227
0.8214	Intermediate Similarity	NPC128951
0.8214	Intermediate Similarity	NPC302578
0.8214	Intermediate Similarity	NPC477924
0.8214	Intermediate Similarity	NPC130136
0.8214	Intermediate Similarity	NPC192046
0.8211	Intermediate Similarity	NPC476895
0.8202	Intermediate Similarity	NPC477604
0.8193	Intermediate Similarity	NPC317242
0.8191	Intermediate Similarity	NPC227583
0.8191	Intermediate Similarity	NPC98457
0.8191	Intermediate Similarity	NPC304899
0.8191	Intermediate Similarity	NPC12103
0.8191	Intermediate Similarity	NPC253115
0.8182	Intermediate Similarity	NPC205845
0.8172	Intermediate Similarity	NPC477605
0.8171	Intermediate Similarity	NPC470610
0.8163	Intermediate Similarity	NPC475365
0.8161	Intermediate Similarity	NPC218616
0.8161	Intermediate Similarity	NPC201852
0.8161	Intermediate Similarity	NPC47763
0.8161	Intermediate Similarity	NPC50964
0.8161	Intermediate Similarity	NPC101462
0.8161	Intermediate Similarity	NPC296701
0.814	Intermediate Similarity	NPC475679
0.814	Intermediate Similarity	NPC22403
0.8132	Intermediate Similarity	NPC101886
0.8132	Intermediate Similarity	NPC259875
0.8132	Intermediate Similarity	NPC187785
0.8118	Intermediate Similarity	NPC472502
0.8118	Intermediate Similarity	NPC275910
0.8118	Intermediate Similarity	NPC31828
0.8118	Intermediate Similarity	NPC102708
0.8118	Intermediate Similarity	NPC475
0.8118	Intermediate Similarity	NPC85346
0.8118	Intermediate Similarity	NPC472500
0.8118	Intermediate Similarity	NPC302041
0.8118	Intermediate Similarity	NPC18857
0.8118	Intermediate Similarity	NPC65897
0.8118	Intermediate Similarity	NPC472499
0.8118	Intermediate Similarity	NPC67657
0.8111	Intermediate Similarity	NPC304083
0.8111	Intermediate Similarity	NPC477600
0.8111	Intermediate Similarity	NPC475313
0.8105	Intermediate Similarity	NPC190554
0.8095	Intermediate Similarity	NPC189883
0.8095	Intermediate Similarity	NPC129165
0.8095	Intermediate Similarity	NPC321016
0.8095	Intermediate Similarity	NPC107059
0.8095	Intermediate Similarity	NPC91573
0.8095	Intermediate Similarity	NPC477925
0.8095	Intermediate Similarity	NPC113733
0.8095	Intermediate Similarity	NPC300324
0.8095	Intermediate Similarity	NPC321381
0.8095	Intermediate Similarity	NPC96319
0.8095	Intermediate Similarity	NPC240604
0.8095	Intermediate Similarity	NPC274079
0.8095	Intermediate Similarity	NPC134330
0.809	Intermediate Similarity	NPC474349
0.809	Intermediate Similarity	NPC474189
0.8085	Intermediate Similarity	NPC476894
0.8072	Intermediate Similarity	NPC48795
0.8072	Intermediate Similarity	NPC308440
0.8072	Intermediate Similarity	NPC472503
0.8068	Intermediate Similarity	NPC134481
0.8068	Intermediate Similarity	NPC470558
0.8068	Intermediate Similarity	NPC82623
0.8068	Intermediate Similarity	NPC474634
0.8061	Intermediate Similarity	NPC475701
0.8061	Intermediate Similarity	NPC191892
0.8046	Intermediate Similarity	NPC476646
0.8046	Intermediate Similarity	NPC23852
0.8046	Intermediate Similarity	NPC209620
0.8043	Intermediate Similarity	NPC192437
0.8043	Intermediate Similarity	NPC270511

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 NPC475664 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1724
0.2-0.3	4377
0.3-0.4	2022
0.4-0.5	408
0.5-0.6	183
0.6-0.7	184
0.7-0.8	71
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7525	Registered
0.8095	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7339	Approved
0.7976	Intermediate Similarity	NPD6942	Approved
0.7717	Intermediate Similarity	NPD7524	Approved
0.7717	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6933	Approved
0.7647	Intermediate Similarity	NPD4785	Approved
0.7647	Intermediate Similarity	NPD4784	Approved
0.7614	Intermediate Similarity	NPD7645	Phase 2
0.7614	Intermediate Similarity	NPD6929	Approved
0.759	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6932	Approved
0.7582	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD6930	Phase 2
0.7528	Intermediate Similarity	NPD6931	Approved
0.75	Intermediate Similarity	NPD7145	Approved
0.7473	Intermediate Similarity	NPD6695	Phase 3
0.7442	Intermediate Similarity	NPD6924	Approved
0.7442	Intermediate Similarity	NPD6926	Approved
0.7429	Intermediate Similarity	NPD4634	Approved
0.7412	Intermediate Similarity	NPD7152	Approved
0.7412	Intermediate Similarity	NPD7150	Approved
0.7412	Intermediate Similarity	NPD7151	Approved
0.7412	Intermediate Similarity	NPD4243	Approved
0.74	Intermediate Similarity	NPD5286	Approved
0.74	Intermediate Similarity	NPD5285	Approved
0.74	Intermediate Similarity	NPD4696	Approved
0.7391	Intermediate Similarity	NPD4786	Approved
0.7386	Intermediate Similarity	NPD6925	Approved
0.7386	Intermediate Similarity	NPD5776	Phase 2
0.7374	Intermediate Similarity	NPD4755	Approved
0.7333	Intermediate Similarity	NPD7514	Phase 3
0.7333	Intermediate Similarity	NPD4748	Discontinued
0.732	Intermediate Similarity	NPD4202	Approved
0.73	Intermediate Similarity	NPD7638	Approved
0.7294	Intermediate Similarity	NPD7143	Approved
0.7294	Intermediate Similarity	NPD7144	Approved
0.7255	Intermediate Similarity	NPD5225	Approved
0.7255	Intermediate Similarity	NPD4633	Approved
0.7255	Intermediate Similarity	NPD5226	Approved
0.7255	Intermediate Similarity	NPD5224	Approved
0.7255	Intermediate Similarity	NPD5211	Phase 2
0.7253	Intermediate Similarity	NPD6902	Approved
0.7228	Intermediate Similarity	NPD4700	Approved
0.7228	Intermediate Similarity	NPD7640	Approved
0.7228	Intermediate Similarity	NPD7639	Approved
0.7222	Intermediate Similarity	NPD6683	Phase 2
0.7216	Intermediate Similarity	NPD6079	Approved
0.7207	Intermediate Similarity	NPD7516	Approved
0.7188	Intermediate Similarity	NPD5328	Approved
0.7184	Intermediate Similarity	NPD5174	Approved
0.7184	Intermediate Similarity	NPD5175	Approved
0.7176	Intermediate Similarity	NPD6922	Approved
0.7176	Intermediate Similarity	NPD6923	Approved
0.7174	Intermediate Similarity	NPD3667	Approved
0.7158	Intermediate Similarity	NPD7750	Discontinued
0.7157	Intermediate Similarity	NPD5223	Approved
0.7143	Intermediate Similarity	NPD7509	Discontinued
0.7143	Intermediate Similarity	NPD7332	Phase 2
0.7128	Intermediate Similarity	NPD6893	Approved
0.7117	Intermediate Similarity	NPD7328	Approved
0.7117	Intermediate Similarity	NPD7327	Approved
0.7115	Intermediate Similarity	NPD5141	Approved
0.708	Intermediate Similarity	NPD8033	Approved
0.7075	Intermediate Similarity	NPD6881	Approved
0.7075	Intermediate Similarity	NPD6899	Approved
0.7064	Intermediate Similarity	NPD4632	Approved
0.7053	Intermediate Similarity	NPD3618	Phase 1
0.7048	Intermediate Similarity	NPD6675	Approved
0.7048	Intermediate Similarity	NPD6402	Approved
0.7048	Intermediate Similarity	NPD7128	Approved
0.7048	Intermediate Similarity	NPD5739	Approved
0.7033	Intermediate Similarity	NPD4195	Approved
0.7021	Intermediate Similarity	NPD3133	Approved
0.7021	Intermediate Similarity	NPD3666	Approved
0.7021	Intermediate Similarity	NPD3665	Phase 1
0.701	Intermediate Similarity	NPD4753	Phase 2
0.6991	Remote Similarity	NPD8377	Approved
0.6991	Remote Similarity	NPD8294	Approved
0.6981	Remote Similarity	NPD6412	Phase 2
0.6981	Remote Similarity	NPD5697	Approved
0.6972	Remote Similarity	NPD8297	Approved
0.697	Remote Similarity	NPD6399	Phase 3
0.6966	Remote Similarity	NPD4190	Phase 3
0.6966	Remote Similarity	NPD5275	Approved
0.6947	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7290	Approved
0.6944	Remote Similarity	NPD6883	Approved
0.6944	Remote Similarity	NPD7102	Approved
0.6931	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5222	Approved
0.6931	Remote Similarity	NPD5221	Approved
0.693	Remote Similarity	NPD8380	Approved
0.693	Remote Similarity	NPD8335	Approved
0.693	Remote Similarity	NPD8379	Approved
0.693	Remote Similarity	NPD8296	Approved
0.693	Remote Similarity	NPD8378	Approved
0.6916	Remote Similarity	NPD4730	Approved
0.6916	Remote Similarity	NPD7320	Approved
0.6916	Remote Similarity	NPD4729	Approved
0.6897	Remote Similarity	NPD4787	Phase 1
0.6887	Remote Similarity	NPD4768	Approved
0.6887	Remote Similarity	NPD4767	Approved
0.6882	Remote Similarity	NPD6898	Phase 1
0.6881	Remote Similarity	NPD6869	Approved
0.6881	Remote Similarity	NPD6649	Approved
0.6881	Remote Similarity	NPD6650	Approved
0.6881	Remote Similarity	NPD8130	Phase 1
0.6881	Remote Similarity	NPD6847	Approved
0.6881	Remote Similarity	NPD6617	Approved
0.6869	Remote Similarity	NPD7087	Discontinued
0.6863	Remote Similarity	NPD5173	Approved
0.6857	Remote Similarity	NPD4754	Approved
0.6852	Remote Similarity	NPD6373	Approved
0.6852	Remote Similarity	NPD6372	Approved
0.6852	Remote Similarity	NPD6013	Approved
0.6852	Remote Similarity	NPD6014	Approved
0.6852	Remote Similarity	NPD6012	Approved
0.6842	Remote Similarity	NPD6319	Approved
0.6842	Remote Similarity	NPD6054	Approved
0.6832	Remote Similarity	NPD4629	Approved
0.6832	Remote Similarity	NPD5210	Approved
0.6827	Remote Similarity	NPD4159	Approved
0.6822	Remote Similarity	NPD5701	Approved
0.6818	Remote Similarity	NPD6882	Approved
0.6789	Remote Similarity	NPD5251	Approved
0.6789	Remote Similarity	NPD5247	Approved
0.6789	Remote Similarity	NPD5248	Approved
0.6789	Remote Similarity	NPD5250	Approved
0.6789	Remote Similarity	NPD5249	Phase 3
0.6783	Remote Similarity	NPD7503	Approved
0.6774	Remote Similarity	NPD6928	Phase 2
0.6765	Remote Similarity	NPD4697	Phase 3
0.6759	Remote Similarity	NPD5128	Approved
0.6759	Remote Similarity	NPD6011	Approved
0.6739	Remote Similarity	NPD6114	Approved
0.6739	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6115	Approved
0.6739	Remote Similarity	NPD6697	Approved
0.6739	Remote Similarity	NPD6118	Approved
0.6737	Remote Similarity	NPD4788	Approved
0.6727	Remote Similarity	NPD5215	Approved
0.6727	Remote Similarity	NPD5217	Approved
0.6727	Remote Similarity	NPD5216	Approved
0.6726	Remote Similarity	NPD6009	Approved
0.6724	Remote Similarity	NPD6370	Approved
0.67	Remote Similarity	NPD8034	Phase 2
0.67	Remote Similarity	NPD7515	Phase 2
0.67	Remote Similarity	NPD7637	Suspended
0.67	Remote Similarity	NPD8035	Phase 2
0.6699	Remote Similarity	NPD6083	Phase 2
0.6699	Remote Similarity	NPD6084	Phase 2
0.6696	Remote Similarity	NPD6059	Approved
0.6695	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6638	Remote Similarity	NPD6015	Approved
0.6638	Remote Similarity	NPD6016	Approved
0.6636	Remote Similarity	NPD5135	Approved
0.6636	Remote Similarity	NPD5169	Approved
0.6636	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD8171	Discontinued
0.6632	Remote Similarity	NPD4221	Approved
0.6632	Remote Similarity	NPD4223	Phase 3
0.663	Remote Similarity	NPD6116	Phase 1
0.661	Remote Similarity	NPD7492	Approved
0.6604	Remote Similarity	NPD7632	Discontinued
0.66	Remote Similarity	NPD7136	Phase 2
0.6598	Remote Similarity	NPD5329	Approved
0.6593	Remote Similarity	NPD8264	Approved
0.6583	Remote Similarity	NPD7736	Approved
0.6581	Remote Similarity	NPD5988	Approved
0.6579	Remote Similarity	NPD7115	Discovery
0.6577	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5127	Approved
0.6574	Remote Similarity	NPD6008	Approved
0.6555	Remote Similarity	NPD6616	Approved
0.6529	Remote Similarity	NPD7319	Approved
0.6525	Remote Similarity	NPD7604	Phase 2
0.6522	Remote Similarity	NPD6117	Approved
0.65	Remote Similarity	NPD6051	Approved
0.65	Remote Similarity	NPD7078	Approved
0.6496	Remote Similarity	NPD5983	Phase 2
0.6495	Remote Similarity	NPD4197	Approved
0.6476	Remote Similarity	NPD5290	Discontinued
0.6476	Remote Similarity	NPD4225	Approved
0.6466	Remote Similarity	NPD7100	Approved
0.6466	Remote Similarity	NPD4522	Approved
0.6466	Remote Similarity	NPD7101	Approved
0.6444	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4819	Approved
0.6421	Remote Similarity	NPD4821	Approved
0.6421	Remote Similarity	NPD4822	Approved
0.6421	Remote Similarity	NPD4820	Approved
0.6417	Remote Similarity	NPD6336	Discontinued
0.6413	Remote Similarity	NPD3703	Phase 2
0.6408	Remote Similarity	NPD7748	Approved
0.6404	Remote Similarity	NPD5167	Approved
0.64	Remote Similarity	NPD7513	Clinical (unspecified phase)

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