NPASS Compound

Structure

NPC186145 OpenBabel07101718312D 33 36 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 -7.4106 -5.2859 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 -5.7633 -5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1235 -4.1270 0.0000 C 0 0 2 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 -6.4325 -5.0780 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 -6.0724 -6.7722 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 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 28 1 0 0 0 0 11 27 1 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 29 1 0 0 0 0 15 1 1 6 0 0 0 15 17 1 0 0 0 0 16 2 1 6 0 0 0 16 20 1 0 0 0 0 17 3 1 1 0 0 0 18 12 1 6 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 27 1 1 0 0 0 20 28 1 1 0 0 0 21 26 1 0 0 0 0 21 30 1 1 0 0 0 22 25 1 0 0 0 0 22 31 1 6 0 0 0 23 24 1 0 0 0 0 23 32 1 1 0 0 0 24 28 1 1 0 0 0 25 26 1 0 0 0 0 25 27 1 1 0 0 0 26 33 1 1 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.35
Volume:	499.933
LogP:	4.088
LogD:	4.177
LogS:	-3.642
# Rotatable Bonds:	5
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.402
Synthetic Accessibility Score:	5.234
Fsp3:	0.929
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:	-5.128
MDCK Permeability:	8.600799628766254e-05
Pgp-inhibitor:	0.889
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.934
20% Bioavailability (F20%):	0.585
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	84.8022232055664%
Volume Distribution (VD):	0.673
Pgp-substrate:	1.9386467933654785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.297
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.18
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.138
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	1.462
Half-life (T1/2):	0.516

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.288
Drug-inuced Liver Injury (DILI):	0.072
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.319
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.523
Carcinogencity:	0.018
Eye Corrosion:	0.005
Eye Irritation:	0.032
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC186145

Natural Product ID:	NPC186145
*Common Name:**	Certonardosterol B2
IUPAC Name:	(3S,4R,5S,6S,8R,9S,10R,13R,14S,15R,17R)-17-[(E,2R,5R,6S)-7-hydroxy-5,6-dimethylhept-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 B2
Standard InCHIKey:	KCGCBQKWOISAIN-PEMGVVNGSA-N
Standard InCHI:	InChI=1S/C28H48O5/c1-15(17(3)14-29)6-7-16(2)20-13-23(32)24-18-12-22(31)25-26(33)21(30)9-11-27(25,4)19(18)8-10-28(20,24)5/h6-7,15-26,29-33H,8-14H2,1-5H3/b7-6+/t15-,16-,17-,18-,19+,20-,21+,22+,23-,24-,25+,26+,27-,28-/m1/s1
SMILES:	C[C@H](/C=C/[C@@H](C)[C@H]1C[C@H]([C@H]2[C@@H]3C[C@@H]([C@H]4[C@H]([C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)O)O)O)[C@H](C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463508
PubChem CID:	11363273
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
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
NPT81	Cell Line	A549	Homo sapiens	ED50	=	2.33	ug ml-1	PMID[495495]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	2.64	ug ml-1	PMID[495495]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	2.23	ug ml-1	PMID[495495]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	2.21	ug ml-1	PMID[495495]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	2.71	ug ml-1	PMID[495495]

☑ 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 NPC186145 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	190
0.1-0.2	1538
0.2-0.3	6100
0.3-0.4	15238
0.4-0.5	8255
0.5-0.6	4792
0.6-0.7	4692
0.7-0.8	1665
0.8-0.85	168
0.85-0.9	39
0.9-0.95	12
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474657
0.9878	High Similarity	NPC475664
0.9759	High Similarity	NPC109744
0.9643	High Similarity	NPC473956
0.9643	High Similarity	NPC475751
0.9506	High Similarity	NPC141941
0.9506	High Similarity	NPC193870
0.9398	High Similarity	NPC6605
0.939	High Similarity	NPC127606
0.939	High Similarity	NPC475798
0.9294	High Similarity	NPC105495
0.9268	High Similarity	NPC110778
0.9268	High Similarity	NPC477818
0.9167	High Similarity	NPC201273
0.9167	High Similarity	NPC139724
0.9157	High Similarity	NPC255882
0.9036	High Similarity	NPC207013
0.9	High Similarity	NPC477226
0.8941	High Similarity	NPC24277
0.8941	High Similarity	NPC269058
0.8941	High Similarity	NPC121981
0.8941	High Similarity	NPC71520
0.8929	High Similarity	NPC124172
0.8864	High Similarity	NPC275671
0.881	High Similarity	NPC85095
0.881	High Similarity	NPC216420
0.881	High Similarity	NPC211135
0.8736	High Similarity	NPC133588
0.8706	High Similarity	NPC209802
0.869	High Similarity	NPC1272
0.869	High Similarity	NPC470614
0.869	High Similarity	NPC30166
0.8681	High Similarity	NPC471903
0.8675	High Similarity	NPC236237
0.8675	High Similarity	NPC236112
0.8675	High Similarity	NPC13554
0.8675	High Similarity	NPC71535
0.8675	High Similarity	NPC78545
0.8675	High Similarity	NPC102253
0.8675	High Similarity	NPC322313
0.8659	High Similarity	NPC6978
0.8659	High Similarity	NPC167037
0.8659	High Similarity	NPC477817
0.8659	High Similarity	NPC138621
0.8659	High Similarity	NPC477819
0.8659	High Similarity	NPC244385
0.8652	High Similarity	NPC97404
0.8652	High Similarity	NPC41554
0.8621	High Similarity	NPC470620
0.8588	High Similarity	NPC113978
0.8588	High Similarity	NPC232023
0.8587	High Similarity	NPC476021
0.8587	High Similarity	NPC316604
0.8587	High Similarity	NPC476040
0.8587	High Similarity	NPC474994
0.8571	High Similarity	NPC474531
0.8556	High Similarity	NPC98193
0.8554	High Similarity	NPC273410
0.8554	High Similarity	NPC1319
0.8554	High Similarity	NPC80530
0.8539	High Similarity	NPC204188
0.8539	High Similarity	NPC329596
0.8539	High Similarity	NPC80561
0.8539	High Similarity	NPC3345
0.8539	High Similarity	NPC291484
0.8539	High Similarity	NPC11216
0.8523	High Similarity	NPC67872
0.8523	High Similarity	NPC474668
0.8523	High Similarity	NPC470542
0.8519	High Similarity	NPC103822
0.8506	High Similarity	NPC237344
0.8506	High Similarity	NPC94462
0.8506	High Similarity	NPC299068
0.8488	Intermediate Similarity	NPC469878
0.8452	Intermediate Similarity	NPC26117
0.8452	Intermediate Similarity	NPC287749
0.8444	Intermediate Similarity	NPC210268
0.8438	Intermediate Similarity	NPC312774
0.8434	Intermediate Similarity	NPC148977
0.8434	Intermediate Similarity	NPC285761
0.8427	Intermediate Similarity	NPC470361
0.8415	Intermediate Similarity	NPC163597
0.8415	Intermediate Similarity	NPC237460
0.8404	Intermediate Similarity	NPC208358
0.8391	Intermediate Similarity	NPC318390
0.8391	Intermediate Similarity	NPC470360
0.8387	Intermediate Similarity	NPC475032
0.8387	Intermediate Similarity	NPC475033
0.8372	Intermediate Similarity	NPC253402
0.8372	Intermediate Similarity	NPC159168
0.8353	Intermediate Similarity	NPC470383
0.8333	Intermediate Similarity	NPC472463
0.8333	Intermediate Similarity	NPC24504
0.8333	Intermediate Similarity	NPC476316
0.8333	Intermediate Similarity	NPC107189
0.8316	Intermediate Similarity	NPC155974
0.8315	Intermediate Similarity	NPC212596
0.8315	Intermediate Similarity	NPC4574
0.8315	Intermediate Similarity	NPC475605
0.8315	Intermediate Similarity	NPC2158
0.8313	Intermediate Similarity	NPC105208
0.8313	Intermediate Similarity	NPC192046
0.8313	Intermediate Similarity	NPC477227
0.8313	Intermediate Similarity	NPC128951
0.8313	Intermediate Similarity	NPC130136
0.8313	Intermediate Similarity	NPC302578
0.8295	Intermediate Similarity	NPC261266
0.8295	Intermediate Similarity	NPC293287
0.8295	Intermediate Similarity	NPC152808
0.8295	Intermediate Similarity	NPC6391
0.8293	Intermediate Similarity	NPC317242
0.828	Intermediate Similarity	NPC288970
0.8276	Intermediate Similarity	NPC256567
0.8276	Intermediate Similarity	NPC474493
0.8276	Intermediate Similarity	NPC185568
0.8276	Intermediate Similarity	NPC238992
0.8272	Intermediate Similarity	NPC470610
0.8261	Intermediate Similarity	NPC65402
0.8261	Intermediate Similarity	NPC127718
0.8256	Intermediate Similarity	NPC296701
0.8256	Intermediate Similarity	NPC47763
0.8256	Intermediate Similarity	NPC248886
0.8256	Intermediate Similarity	NPC218616
0.8256	Intermediate Similarity	NPC7988
0.8247	Intermediate Similarity	NPC475365
0.8235	Intermediate Similarity	NPC475679
0.8235	Intermediate Similarity	NPC47149
0.8222	Intermediate Similarity	NPC259875
0.8222	Intermediate Similarity	NPC187785
0.8222	Intermediate Similarity	NPC101886
0.8214	Intermediate Similarity	NPC18857
0.8214	Intermediate Similarity	NPC65897
0.8214	Intermediate Similarity	NPC472500
0.8214	Intermediate Similarity	NPC472499
0.8214	Intermediate Similarity	NPC85346
0.8214	Intermediate Similarity	NPC67657
0.8214	Intermediate Similarity	NPC302041
0.8214	Intermediate Similarity	NPC475
0.8214	Intermediate Similarity	NPC477522
0.8214	Intermediate Similarity	NPC472502
0.8214	Intermediate Similarity	NPC87604
0.8214	Intermediate Similarity	NPC31828
0.8214	Intermediate Similarity	NPC102708
0.8202	Intermediate Similarity	NPC271967
0.8202	Intermediate Similarity	NPC477600
0.8202	Intermediate Similarity	NPC304083
0.8193	Intermediate Similarity	NPC129165
0.8193	Intermediate Similarity	NPC189883
0.8193	Intermediate Similarity	NPC134330
0.8193	Intermediate Similarity	NPC91573
0.8191	Intermediate Similarity	NPC476893
0.8172	Intermediate Similarity	NPC8774
0.8171	Intermediate Similarity	NPC48795
0.8171	Intermediate Similarity	NPC472503
0.8171	Intermediate Similarity	NPC308440
0.8161	Intermediate Similarity	NPC134481
0.8161	Intermediate Similarity	NPC82623
0.8161	Intermediate Similarity	NPC470558
0.8161	Intermediate Similarity	NPC317458
0.8152	Intermediate Similarity	NPC310013
0.814	Intermediate Similarity	NPC157655
0.8118	Intermediate Similarity	NPC472742
0.8118	Intermediate Similarity	NPC328714
0.8118	Intermediate Similarity	NPC475727
0.8118	Intermediate Similarity	NPC80297
0.8118	Intermediate Similarity	NPC116119
0.8111	Intermediate Similarity	NPC280556
0.8111	Intermediate Similarity	NPC473436
0.8105	Intermediate Similarity	NPC280825
0.8105	Intermediate Similarity	NPC476895
0.8105	Intermediate Similarity	NPC102426
0.8105	Intermediate Similarity	NPC300179
0.8105	Intermediate Similarity	NPC234287
0.8095	Intermediate Similarity	NPC185915
0.8095	Intermediate Similarity	NPC138502
0.8095	Intermediate Similarity	NPC260301
0.8095	Intermediate Similarity	NPC202540
0.8095	Intermediate Similarity	NPC477924
0.8095	Intermediate Similarity	NPC214570
0.8095	Intermediate Similarity	NPC471798
0.8095	Intermediate Similarity	NPC307336
0.809	Intermediate Similarity	NPC477604
0.809	Intermediate Similarity	NPC125399
0.8085	Intermediate Similarity	NPC12103
0.8085	Intermediate Similarity	NPC304899
0.8085	Intermediate Similarity	NPC253115
0.8085	Intermediate Similarity	NPC227583
0.8085	Intermediate Similarity	NPC98457
0.8072	Intermediate Similarity	NPC471723
0.8072	Intermediate Similarity	NPC141071
0.8072	Intermediate Similarity	NPC257347
0.8072	Intermediate Similarity	NPC196136
0.8072	Intermediate Similarity	NPC243027
0.8072	Intermediate Similarity	NPC3403
0.8072	Intermediate Similarity	NPC158208
0.8068	Intermediate Similarity	NPC478102
0.8068	Intermediate Similarity	NPC205845
0.8065	Intermediate Similarity	NPC477605
0.8065	Intermediate Similarity	NPC111015
0.8049	Intermediate Similarity	NPC153719

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 NPC186145 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1757
0.2-0.3	4413
0.3-0.4	1985
0.4-0.5	387
0.5-0.6	170
0.6-0.7	183
0.7-0.8	78
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8675	High Similarity	NPD7525	Registered
0.7976	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6942	Approved
0.7857	Intermediate Similarity	NPD7339	Approved
0.7701	Intermediate Similarity	NPD7645	Phase 2
0.7683	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD7524	Approved
0.7558	Intermediate Similarity	NPD6933	Approved
0.7529	Intermediate Similarity	NPD4784	Approved
0.7529	Intermediate Similarity	NPD4785	Approved
0.75	Intermediate Similarity	NPD6929	Approved
0.75	Intermediate Similarity	NPD4243	Approved
0.75	Intermediate Similarity	NPD4634	Approved
0.7475	Intermediate Similarity	NPD5285	Approved
0.7475	Intermediate Similarity	NPD5286	Approved
0.7475	Intermediate Similarity	NPD4696	Approved
0.7473	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6932	Approved
0.7449	Intermediate Similarity	NPD4755	Approved
0.7416	Intermediate Similarity	NPD6931	Approved
0.7416	Intermediate Similarity	NPD6930	Phase 2
0.7396	Intermediate Similarity	NPD4202	Approved
0.7386	Intermediate Similarity	NPD7145	Approved
0.7374	Intermediate Similarity	NPD7638	Approved
0.7363	Intermediate Similarity	NPD6695	Phase 3
0.7327	Intermediate Similarity	NPD5224	Approved
0.7327	Intermediate Similarity	NPD5211	Phase 2
0.7327	Intermediate Similarity	NPD5225	Approved
0.7327	Intermediate Similarity	NPD4633	Approved
0.7327	Intermediate Similarity	NPD5226	Approved
0.7326	Intermediate Similarity	NPD6924	Approved
0.7326	Intermediate Similarity	NPD6926	Approved
0.73	Intermediate Similarity	NPD4700	Approved
0.73	Intermediate Similarity	NPD7640	Approved
0.73	Intermediate Similarity	NPD7639	Approved
0.7294	Intermediate Similarity	NPD7152	Approved
0.7294	Intermediate Similarity	NPD7150	Approved
0.7294	Intermediate Similarity	NPD7151	Approved
0.7292	Intermediate Similarity	NPD6079	Approved
0.7283	Intermediate Similarity	NPD4786	Approved
0.7273	Intermediate Similarity	NPD7516	Approved
0.7273	Intermediate Similarity	NPD5776	Phase 2
0.7273	Intermediate Similarity	NPD6925	Approved
0.7263	Intermediate Similarity	NPD5328	Approved
0.7255	Intermediate Similarity	NPD5175	Approved
0.7255	Intermediate Similarity	NPD5174	Approved
0.7228	Intermediate Similarity	NPD5223	Approved
0.7222	Intermediate Similarity	NPD7514	Phase 3
0.7222	Intermediate Similarity	NPD4748	Discontinued
0.7184	Intermediate Similarity	NPD5141	Approved
0.7182	Intermediate Similarity	NPD7327	Approved
0.7182	Intermediate Similarity	NPD7328	Approved
0.7176	Intermediate Similarity	NPD7143	Approved
0.7176	Intermediate Similarity	NPD7144	Approved
0.7143	Intermediate Similarity	NPD6902	Approved
0.7143	Intermediate Similarity	NPD6899	Approved
0.7143	Intermediate Similarity	NPD6881	Approved
0.713	Intermediate Similarity	NPD4632	Approved
0.7128	Intermediate Similarity	NPD3618	Phase 1
0.7115	Intermediate Similarity	NPD5739	Approved
0.7115	Intermediate Similarity	NPD6675	Approved
0.7115	Intermediate Similarity	NPD6402	Approved
0.7115	Intermediate Similarity	NPD7128	Approved
0.7111	Intermediate Similarity	NPD6683	Phase 2
0.7111	Intermediate Similarity	NPD4195	Approved
0.7097	Intermediate Similarity	NPD3133	Approved
0.7097	Intermediate Similarity	NPD3665	Phase 1
0.7097	Intermediate Similarity	NPD3666	Approved
0.7083	Intermediate Similarity	NPD4753	Phase 2
0.7065	Intermediate Similarity	NPD3667	Approved
0.7059	Intermediate Similarity	NPD6922	Approved
0.7059	Intermediate Similarity	NPD6923	Approved
0.7054	Intermediate Similarity	NPD8294	Approved
0.7054	Intermediate Similarity	NPD8377	Approved
0.7053	Intermediate Similarity	NPD7750	Discontinued
0.7048	Intermediate Similarity	NPD6412	Phase 2
0.7048	Intermediate Similarity	NPD5697	Approved
0.7045	Intermediate Similarity	NPD5275	Approved
0.7045	Intermediate Similarity	NPD4190	Phase 3
0.7037	Intermediate Similarity	NPD8297	Approved
0.7033	Intermediate Similarity	NPD7509	Discontinued
0.7033	Intermediate Similarity	NPD7332	Phase 2
0.7021	Intermediate Similarity	NPD6893	Approved
0.7021	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6883	Approved
0.7009	Intermediate Similarity	NPD7102	Approved
0.7009	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5221	Approved
0.7	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD8033	Approved
0.6991	Remote Similarity	NPD8296	Approved
0.6991	Remote Similarity	NPD8380	Approved
0.6991	Remote Similarity	NPD8379	Approved
0.6991	Remote Similarity	NPD8335	Approved
0.6991	Remote Similarity	NPD8378	Approved
0.6981	Remote Similarity	NPD4730	Approved
0.6981	Remote Similarity	NPD4729	Approved
0.6981	Remote Similarity	NPD7320	Approved
0.6977	Remote Similarity	NPD4787	Phase 1
0.6952	Remote Similarity	NPD4768	Approved
0.6952	Remote Similarity	NPD4767	Approved
0.6944	Remote Similarity	NPD6869	Approved
0.6944	Remote Similarity	NPD6649	Approved
0.6944	Remote Similarity	NPD6847	Approved
0.6944	Remote Similarity	NPD8130	Phase 1
0.6944	Remote Similarity	NPD6650	Approved
0.6944	Remote Similarity	NPD6617	Approved
0.6931	Remote Similarity	NPD5173	Approved
0.6923	Remote Similarity	NPD4754	Approved
0.6916	Remote Similarity	NPD6373	Approved
0.6916	Remote Similarity	NPD6372	Approved
0.6916	Remote Similarity	NPD6014	Approved
0.6916	Remote Similarity	NPD6012	Approved
0.6916	Remote Similarity	NPD6013	Approved
0.6903	Remote Similarity	NPD6319	Approved
0.6903	Remote Similarity	NPD6054	Approved
0.69	Remote Similarity	NPD5210	Approved
0.69	Remote Similarity	NPD4629	Approved
0.6887	Remote Similarity	NPD5701	Approved
0.6881	Remote Similarity	NPD6882	Approved
0.6869	Remote Similarity	NPD6399	Phase 3
0.6852	Remote Similarity	NPD5247	Approved
0.6852	Remote Similarity	NPD5251	Approved
0.6852	Remote Similarity	NPD5249	Phase 3
0.6852	Remote Similarity	NPD5248	Approved
0.6852	Remote Similarity	NPD5250	Approved
0.6848	Remote Similarity	NPD6928	Phase 2
0.6842	Remote Similarity	NPD7503	Approved
0.6832	Remote Similarity	NPD4697	Phase 3
0.6822	Remote Similarity	NPD6011	Approved
0.6822	Remote Similarity	NPD5128	Approved
0.6813	Remote Similarity	NPD6118	Approved
0.6813	Remote Similarity	NPD6114	Approved
0.6813	Remote Similarity	NPD6115	Approved
0.6813	Remote Similarity	NPD6697	Approved
0.6809	Remote Similarity	NPD4788	Approved
0.6789	Remote Similarity	NPD5216	Approved
0.6789	Remote Similarity	NPD5215	Approved
0.6789	Remote Similarity	NPD5217	Approved
0.6786	Remote Similarity	NPD6009	Approved
0.6783	Remote Similarity	NPD6370	Approved
0.6774	Remote Similarity	NPD6898	Phase 1
0.6768	Remote Similarity	NPD7087	Discontinued
0.6768	Remote Similarity	NPD7515	Phase 2
0.6768	Remote Similarity	NPD8034	Phase 2
0.6768	Remote Similarity	NPD8035	Phase 2
0.6765	Remote Similarity	NPD6084	Phase 2
0.6765	Remote Similarity	NPD6083	Phase 2
0.6754	Remote Similarity	NPD6059	Approved
0.6752	Remote Similarity	NPD7507	Approved
0.6731	Remote Similarity	NPD4159	Approved
0.6703	Remote Similarity	NPD6116	Phase 1
0.6702	Remote Similarity	NPD4221	Approved
0.6702	Remote Similarity	NPD4223	Phase 3
0.67	Remote Similarity	NPD8171	Discontinued
0.6697	Remote Similarity	NPD5135	Approved
0.6697	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5169	Approved
0.6696	Remote Similarity	NPD6015	Approved
0.6696	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD5329	Approved
0.6639	Remote Similarity	NPD7736	Approved
0.6638	Remote Similarity	NPD5988	Approved
0.6636	Remote Similarity	NPD5127	Approved
0.6636	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6616	Approved
0.66	Remote Similarity	NPD7637	Suspended
0.6593	Remote Similarity	NPD6117	Approved
0.6583	Remote Similarity	NPD7319	Approved
0.6581	Remote Similarity	NPD7604	Phase 2
0.6566	Remote Similarity	NPD6051	Approved
0.6562	Remote Similarity	NPD3668	Phase 3
0.6562	Remote Similarity	NPD4197	Approved
0.6555	Remote Similarity	NPD7078	Approved
0.6552	Remote Similarity	NPD5983	Phase 2
0.6538	Remote Similarity	NPD5290	Discontinued
0.6522	Remote Similarity	NPD7101	Approved
0.6522	Remote Similarity	NPD4522	Approved
0.6522	Remote Similarity	NPD7100	Approved
0.6517	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7136	Phase 2
0.6491	Remote Similarity	NPD7115	Discovery
0.6484	Remote Similarity	NPD8264	Approved
0.6484	Remote Similarity	NPD3703	Phase 2
0.6481	Remote Similarity	NPD6008	Approved
0.6471	Remote Similarity	NPD7748	Approved
0.6471	Remote Similarity	NPD6336	Discontinued
0.6465	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5167	Approved
0.6442	Remote Similarity	NPD7902	Approved
0.6436	Remote Similarity	NPD5281	Approved
0.6436	Remote Similarity	NPD5284	Approved
0.6435	Remote Similarity	NPD6335	Approved
0.6429	Remote Similarity	NPD4689	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