NPASS Compound

Structure

NPC109744 OpenBabel07101718202D 34 37 0 0 1 0 0 0 0 0999 V2000 -5.0605 -3.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4570 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6786 -5.2859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 -2.4135 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 -3.4133 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 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 -4.0313 -5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3914 -4.1270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1261 -2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7004 -5.0780 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 2 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 0.8660 -0.5000 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 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 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 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3403 -6.7722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 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 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 22 1 0 0 0 0 10 27 1 0 0 0 0 11 26 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 13 28 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 18 1 0 0 0 0 17 3 1 1 0 0 0 18 26 1 1 0 0 0 19 24 1 0 0 0 0 19 30 1 1 0 0 0 20 25 1 0 0 0 0 20 31 1 1 0 0 0 21 23 1 0 0 0 0 21 32 1 6 0 0 0 22 27 1 1 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 23 27 1 1 0 0 0 24 33 1 1 0 0 0 25 26 1 1 0 0 0 25 28 1 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 28 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.35
Volume:	508.723
LogP:	3.011
LogD:	3.165
LogS:	-3.581
# Rotatable Bonds:	5
TPSA:	121.38
# H-Bond Aceptor:	6
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.336
Synthetic Accessibility Score:	5.365
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:	-5.193
MDCK Permeability:	6.0353784647304565e-05
Pgp-inhibitor:	0.405
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.896
20% Bioavailability (F20%):	0.07
30% Bioavailability (F30%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	83.01691436767578%
Volume Distribution (VD):	0.614
Pgp-substrate:	2.0131149291992188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.836
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.785
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.231
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	1.24
Half-life (T1/2):	0.298

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.379
Maximum Recommended Daily Dose:	0.093
Skin Sensitization:	0.394
Carcinogencity:	0.023
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC109744

Natural Product ID:	NPC109744
*Common Name:**	Certonardosterol A2
IUPAC Name:	(3S,4R,5S,6S,8S,9R,10S,13R,14S,15R,17R)-17-[(E,2R,5R,6S)-7-hydroxy-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,4,6,8,15-pentol
Synonyms:	Certonardosterol A2
Standard InCHIKey:	UZMSBSHNTQAMIG-OYNHBLERSA-N
Standard InCHI:	InChI=1S/C28H48O6/c1-15(17(3)14-29)6-7-16(2)18-12-20(31)25-26(18,4)11-9-22-27(5)10-8-19(30)24(33)23(27)21(32)13-28(22,25)34/h6-7,15-25,29-34H,8-14H2,1-5H3/b7-6+/t15-,16-,17-,18-,19+,20-,21+,22-,23+,24+,25-,26-,27-,28+/m1/s1
SMILES:	OC[C@H]([C@@H](/C=C/[C@H]([C@H]1C[C@H]([C@@H]2[C@]1(C)CC[C@H]1[C@@]2(O)C[C@@H]([C@@H]2[C@]1(C)CC[C@@H]([C@@H]2O)O)O)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463509
PubChem CID:	11454468
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	=	1.75	ug ml-1	PMID[495923]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	1.13	ug ml-1	PMID[495923]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	0.67	ug ml-1	PMID[495923]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	0.89	ug ml-1	PMID[495923]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	2.54	ug ml-1	PMID[495923]

☑ 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 NPC109744 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	193
0.1-0.2	1626
0.2-0.3	6125
0.3-0.4	14963
0.4-0.5	8432
0.5-0.6	4871
0.6-0.7	4670
0.7-0.8	1605
0.8-0.85	125
0.85-0.9	63
0.9-0.95	17
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC475751
0.9881	High Similarity	NPC473956
0.9759	High Similarity	NPC474657
0.9759	High Similarity	NPC186145
0.9643	High Similarity	NPC475664
0.9639	High Similarity	NPC6605
0.9405	High Similarity	NPC201273
0.9277	High Similarity	NPC141941
0.9277	High Similarity	NPC193870
0.9222	High Similarity	NPC477226
0.9176	High Similarity	NPC121981
0.9167	High Similarity	NPC127606
0.9167	High Similarity	NPC475798
0.9091	High Similarity	NPC275671
0.908	High Similarity	NPC105495
0.9048	High Similarity	NPC110778
0.9048	High Similarity	NPC216420
0.9048	High Similarity	NPC477818
0.9048	High Similarity	NPC211135
0.9048	High Similarity	NPC207013
0.9048	High Similarity	NPC85095
0.8953	High Similarity	NPC71520
0.8953	High Similarity	NPC139724
0.8953	High Similarity	NPC269058
0.8941	High Similarity	NPC255882
0.8901	High Similarity	NPC471903
0.8876	High Similarity	NPC41554
0.8876	High Similarity	NPC97404
0.8824	High Similarity	NPC232023
0.8804	High Similarity	NPC476021
0.8804	High Similarity	NPC316604
0.8804	High Similarity	NPC474994
0.8804	High Similarity	NPC476040
0.8764	High Similarity	NPC204188
0.8764	High Similarity	NPC291484
0.8764	High Similarity	NPC3345
0.8764	High Similarity	NPC80561
0.8764	High Similarity	NPC11216
0.8764	High Similarity	NPC329596
0.875	High Similarity	NPC133588
0.8736	High Similarity	NPC299068
0.8736	High Similarity	NPC24277
0.8721	High Similarity	NPC124172
0.8706	High Similarity	NPC30166
0.869	High Similarity	NPC236237
0.869	High Similarity	NPC102253
0.869	High Similarity	NPC13554
0.869	High Similarity	NPC322313
0.8652	High Similarity	NPC470361
0.8621	High Similarity	NPC470360
0.8605	High Similarity	NPC113978
0.8571	High Similarity	NPC98193
0.8571	High Similarity	NPC80530
0.8571	High Similarity	NPC273410
0.8554	High Similarity	NPC302578
0.8554	High Similarity	NPC105208
0.8554	High Similarity	NPC477227
0.8554	High Similarity	NPC192046
0.8554	High Similarity	NPC128951
0.8539	High Similarity	NPC474668
0.8539	High Similarity	NPC475605
0.8539	High Similarity	NPC4574
0.8539	High Similarity	NPC212596
0.8523	High Similarity	NPC94462
0.8506	High Similarity	NPC209802
0.8495	Intermediate Similarity	NPC288970
0.8488	Intermediate Similarity	NPC1272
0.8488	Intermediate Similarity	NPC470614
0.8478	Intermediate Similarity	NPC127718
0.8478	Intermediate Similarity	NPC65402
0.8471	Intermediate Similarity	NPC71535
0.8471	Intermediate Similarity	NPC236112
0.8471	Intermediate Similarity	NPC78545
0.8462	Intermediate Similarity	NPC210268
0.8452	Intermediate Similarity	NPC477817
0.8452	Intermediate Similarity	NPC67657
0.8452	Intermediate Similarity	NPC477819
0.8452	Intermediate Similarity	NPC244385
0.8452	Intermediate Similarity	NPC285761
0.8452	Intermediate Similarity	NPC6978
0.8452	Intermediate Similarity	NPC31828
0.8452	Intermediate Similarity	NPC138621
0.8452	Intermediate Similarity	NPC18857
0.8452	Intermediate Similarity	NPC167037
0.8444	Intermediate Similarity	NPC101886
0.8434	Intermediate Similarity	NPC163597
0.8427	Intermediate Similarity	NPC304083
0.8427	Intermediate Similarity	NPC470620
0.8427	Intermediate Similarity	NPC477600
0.8409	Intermediate Similarity	NPC318390
0.8387	Intermediate Similarity	NPC8774
0.8372	Intermediate Similarity	NPC470383
0.8372	Intermediate Similarity	NPC474531
0.837	Intermediate Similarity	NPC310013
0.8353	Intermediate Similarity	NPC1319
0.8333	Intermediate Similarity	NPC470542
0.8333	Intermediate Similarity	NPC185915
0.8333	Intermediate Similarity	NPC67872
0.8333	Intermediate Similarity	NPC473436
0.8315	Intermediate Similarity	NPC237344
0.8315	Intermediate Similarity	NPC261266
0.8315	Intermediate Similarity	NPC152808
0.8315	Intermediate Similarity	NPC6391
0.8315	Intermediate Similarity	NPC293287
0.8313	Intermediate Similarity	NPC103822
0.8313	Intermediate Similarity	NPC196136
0.8313	Intermediate Similarity	NPC243027
0.8313	Intermediate Similarity	NPC317242
0.8313	Intermediate Similarity	NPC158208
0.8298	Intermediate Similarity	NPC98457
0.8298	Intermediate Similarity	NPC227583
0.8298	Intermediate Similarity	NPC12103
0.8295	Intermediate Similarity	NPC469878
0.8295	Intermediate Similarity	NPC474493
0.8295	Intermediate Similarity	NPC256567
0.8276	Intermediate Similarity	NPC296701
0.8276	Intermediate Similarity	NPC218616
0.8276	Intermediate Similarity	NPC7988
0.8265	Intermediate Similarity	NPC312774
0.8261	Intermediate Similarity	NPC219516
0.8256	Intermediate Similarity	NPC475679
0.8256	Intermediate Similarity	NPC287749
0.8256	Intermediate Similarity	NPC26117
0.8242	Intermediate Similarity	NPC74258
0.8242	Intermediate Similarity	NPC138974
0.8242	Intermediate Similarity	NPC259875
0.8242	Intermediate Similarity	NPC187785
0.8235	Intermediate Similarity	NPC148977
0.8229	Intermediate Similarity	NPC208358
0.8214	Intermediate Similarity	NPC91573
0.8214	Intermediate Similarity	NPC237460
0.8211	Intermediate Similarity	NPC475033
0.8211	Intermediate Similarity	NPC475032
0.8211	Intermediate Similarity	NPC476893
0.8193	Intermediate Similarity	NPC228994
0.8193	Intermediate Similarity	NPC192501
0.8193	Intermediate Similarity	NPC304499
0.8193	Intermediate Similarity	NPC10476
0.8182	Intermediate Similarity	NPC134481
0.8182	Intermediate Similarity	NPC470558
0.8182	Intermediate Similarity	NPC159168
0.8182	Intermediate Similarity	NPC82623
0.8182	Intermediate Similarity	NPC470929
0.8182	Intermediate Similarity	NPC253402
0.8152	Intermediate Similarity	NPC107189
0.8152	Intermediate Similarity	NPC192437
0.8152	Intermediate Similarity	NPC270511
0.8152	Intermediate Similarity	NPC14380
0.8152	Intermediate Similarity	NPC470390
0.8152	Intermediate Similarity	NPC245410
0.8144	Intermediate Similarity	NPC155974
0.814	Intermediate Similarity	NPC476316
0.814	Intermediate Similarity	NPC475727
0.814	Intermediate Similarity	NPC472463
0.814	Intermediate Similarity	NPC287452
0.814	Intermediate Similarity	NPC24504
0.814	Intermediate Similarity	NPC328714
0.814	Intermediate Similarity	NPC472742
0.814	Intermediate Similarity	NPC80297
0.814	Intermediate Similarity	NPC116119
0.8132	Intermediate Similarity	NPC280556
0.8132	Intermediate Similarity	NPC2158
0.8125	Intermediate Similarity	NPC300179
0.8125	Intermediate Similarity	NPC102426
0.8125	Intermediate Similarity	NPC476895
0.8118	Intermediate Similarity	NPC130136
0.8111	Intermediate Similarity	NPC125399
0.8105	Intermediate Similarity	NPC210717
0.8105	Intermediate Similarity	NPC103165
0.8095	Intermediate Similarity	NPC3403
0.809	Intermediate Similarity	NPC185568
0.809	Intermediate Similarity	NPC238992
0.809	Intermediate Similarity	NPC205845
0.809	Intermediate Similarity	NPC86238
0.8085	Intermediate Similarity	NPC477605
0.8081	Intermediate Similarity	NPC475365
0.8072	Intermediate Similarity	NPC470610
0.8072	Intermediate Similarity	NPC153719
0.8068	Intermediate Similarity	NPC47763
0.8068	Intermediate Similarity	NPC248886
0.8058	Intermediate Similarity	NPC475312
0.8046	Intermediate Similarity	NPC47149
0.8046	Intermediate Similarity	NPC95124
0.8046	Intermediate Similarity	NPC22403
0.8046	Intermediate Similarity	NPC471266
0.8023	Intermediate Similarity	NPC65897
0.8023	Intermediate Similarity	NPC472500
0.8023	Intermediate Similarity	NPC42853
0.8023	Intermediate Similarity	NPC85346
0.8023	Intermediate Similarity	NPC472499
0.8023	Intermediate Similarity	NPC472501
0.8023	Intermediate Similarity	NPC302041
0.8023	Intermediate Similarity	NPC301707
0.8023	Intermediate Similarity	NPC477522
0.8023	Intermediate Similarity	NPC472502
0.8023	Intermediate Similarity	NPC87604
0.8023	Intermediate Similarity	NPC147993
0.8023	Intermediate Similarity	NPC475
0.8023	Intermediate Similarity	NPC102708
0.8022	Intermediate Similarity	NPC271967

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 NPC109744 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	1845
0.2-0.3	4434
0.3-0.4	1878
0.4-0.5	387
0.5-0.6	167
0.6-0.7	181
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
0.869	High Similarity	NPD7525	Registered
0.7826	Intermediate Similarity	NPD7524	Approved
0.7791	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6932	Approved
0.7692	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6942	Approved
0.7674	Intermediate Similarity	NPD7339	Approved
0.764	Intermediate Similarity	NPD6931	Approved
0.764	Intermediate Similarity	NPD6930	Phase 2
0.7634	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6933	Approved
0.7582	Intermediate Similarity	NPD6695	Phase 3
0.7558	Intermediate Similarity	NPD4785	Approved
0.7558	Intermediate Similarity	NPD4784	Approved
0.7529	Intermediate Similarity	NPD4243	Approved
0.7528	Intermediate Similarity	NPD6929	Approved
0.7528	Intermediate Similarity	NPD7645	Phase 2
0.7524	Intermediate Similarity	NPD4634	Approved
0.75	Intermediate Similarity	NPD5286	Approved
0.75	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD5285	Approved
0.7475	Intermediate Similarity	NPD4755	Approved
0.7455	Intermediate Similarity	NPD7516	Approved
0.7444	Intermediate Similarity	NPD7514	Phase 3
0.7423	Intermediate Similarity	NPD4202	Approved
0.7416	Intermediate Similarity	NPD7145	Approved
0.7364	Intermediate Similarity	NPD7327	Approved
0.7364	Intermediate Similarity	NPD7328	Approved
0.7356	Intermediate Similarity	NPD6926	Approved
0.7356	Intermediate Similarity	NPD6924	Approved
0.7353	Intermediate Similarity	NPD5224	Approved
0.7353	Intermediate Similarity	NPD5211	Phase 2
0.7353	Intermediate Similarity	NPD5225	Approved
0.7353	Intermediate Similarity	NPD5226	Approved
0.7353	Intermediate Similarity	NPD4633	Approved
0.7333	Intermediate Similarity	NPD6683	Phase 2
0.7327	Intermediate Similarity	NPD4700	Approved
0.7303	Intermediate Similarity	NPD5776	Phase 2
0.7303	Intermediate Similarity	NPD6925	Approved
0.7282	Intermediate Similarity	NPD5175	Approved
0.7282	Intermediate Similarity	NPD5174	Approved
0.7263	Intermediate Similarity	NPD7750	Discontinued
0.7255	Intermediate Similarity	NPD5223	Approved
0.7253	Intermediate Similarity	NPD7332	Phase 2
0.7253	Intermediate Similarity	NPD4748	Discontinued
0.7234	Intermediate Similarity	NPD6893	Approved
0.7228	Intermediate Similarity	NPD7638	Approved
0.7212	Intermediate Similarity	NPD5141	Approved
0.7174	Intermediate Similarity	NPD6902	Approved
0.717	Intermediate Similarity	NPD6881	Approved
0.717	Intermediate Similarity	NPD6899	Approved
0.7168	Intermediate Similarity	NPD8296	Approved
0.7168	Intermediate Similarity	NPD8335	Approved
0.7168	Intermediate Similarity	NPD8380	Approved
0.7168	Intermediate Similarity	NPD8379	Approved
0.7168	Intermediate Similarity	NPD8378	Approved
0.7157	Intermediate Similarity	NPD7640	Approved
0.7157	Intermediate Similarity	NPD7639	Approved
0.7156	Intermediate Similarity	NPD4632	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD6079	Approved
0.7143	Intermediate Similarity	NPD4195	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7128	Intermediate Similarity	NPD4786	Approved
0.7126	Intermediate Similarity	NPD7150	Approved
0.7126	Intermediate Similarity	NPD7151	Approved
0.7126	Intermediate Similarity	NPD7152	Approved
0.7113	Intermediate Similarity	NPD5328	Approved
0.7113	Intermediate Similarity	NPD4753	Phase 2
0.708	Intermediate Similarity	NPD8294	Approved
0.708	Intermediate Similarity	NPD8377	Approved
0.7079	Intermediate Similarity	NPD4190	Phase 3
0.7079	Intermediate Similarity	NPD5275	Approved
0.7075	Intermediate Similarity	NPD5697	Approved
0.7065	Intermediate Similarity	NPD7509	Discontinued
0.7064	Intermediate Similarity	NPD8297	Approved
0.7037	Intermediate Similarity	NPD6883	Approved
0.7037	Intermediate Similarity	NPD7290	Approved
0.7037	Intermediate Similarity	NPD7102	Approved
0.7018	Intermediate Similarity	NPD8033	Approved
0.7011	Intermediate Similarity	NPD4787	Phase 1
0.7011	Intermediate Similarity	NPD7144	Approved
0.7011	Intermediate Similarity	NPD7143	Approved
0.7009	Intermediate Similarity	NPD4729	Approved
0.7009	Intermediate Similarity	NPD4730	Approved
0.7009	Intermediate Similarity	NPD7320	Approved
0.6989	Remote Similarity	NPD6898	Phase 1
0.6981	Remote Similarity	NPD4768	Approved
0.6981	Remote Similarity	NPD4767	Approved
0.6979	Remote Similarity	NPD3618	Phase 1
0.6972	Remote Similarity	NPD8130	Phase 1
0.6972	Remote Similarity	NPD6617	Approved
0.6972	Remote Similarity	NPD6649	Approved
0.6972	Remote Similarity	NPD6869	Approved
0.6972	Remote Similarity	NPD6847	Approved
0.6972	Remote Similarity	NPD6650	Approved
0.697	Remote Similarity	NPD7087	Discontinued
0.6952	Remote Similarity	NPD4754	Approved
0.6947	Remote Similarity	NPD3133	Approved
0.6947	Remote Similarity	NPD3665	Phase 1
0.6947	Remote Similarity	NPD3666	Approved
0.6944	Remote Similarity	NPD6373	Approved
0.6944	Remote Similarity	NPD6372	Approved
0.6944	Remote Similarity	NPD6012	Approved
0.6944	Remote Similarity	NPD6013	Approved
0.6944	Remote Similarity	NPD6014	Approved
0.6931	Remote Similarity	NPD4629	Approved
0.6931	Remote Similarity	NPD5210	Approved
0.693	Remote Similarity	NPD6319	Approved
0.693	Remote Similarity	NPD6054	Approved
0.6923	Remote Similarity	NPD4159	Approved
0.6916	Remote Similarity	NPD5701	Approved
0.6916	Remote Similarity	NPD6412	Phase 2
0.6915	Remote Similarity	NPD3667	Approved
0.6909	Remote Similarity	NPD6882	Approved
0.6897	Remote Similarity	NPD6923	Approved
0.6897	Remote Similarity	NPD6922	Approved
0.6881	Remote Similarity	NPD5250	Approved
0.6881	Remote Similarity	NPD5247	Approved
0.6881	Remote Similarity	NPD5249	Phase 3
0.6881	Remote Similarity	NPD5248	Approved
0.6881	Remote Similarity	NPD5251	Approved
0.6875	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7503	Approved
0.6863	Remote Similarity	NPD5221	Approved
0.6863	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5222	Approved
0.6852	Remote Similarity	NPD5128	Approved
0.6852	Remote Similarity	NPD6011	Approved
0.6842	Remote Similarity	NPD4788	Approved
0.6818	Remote Similarity	NPD5215	Approved
0.6818	Remote Similarity	NPD5217	Approved
0.6818	Remote Similarity	NPD5216	Approved
0.6814	Remote Similarity	NPD6009	Approved
0.681	Remote Similarity	NPD6370	Approved
0.6796	Remote Similarity	NPD6084	Phase 2
0.6796	Remote Similarity	NPD6083	Phase 2
0.6796	Remote Similarity	NPD5173	Approved
0.6783	Remote Similarity	NPD6059	Approved
0.678	Remote Similarity	NPD7507	Approved
0.675	Remote Similarity	NPD7319	Approved
0.6737	Remote Similarity	NPD4221	Approved
0.6737	Remote Similarity	NPD4223	Phase 3
0.6733	Remote Similarity	NPD6399	Phase 3
0.6727	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5135	Approved
0.6727	Remote Similarity	NPD5169	Approved
0.6724	Remote Similarity	NPD6015	Approved
0.6724	Remote Similarity	NPD6016	Approved
0.6702	Remote Similarity	NPD6928	Phase 2
0.6701	Remote Similarity	NPD5329	Approved
0.6699	Remote Similarity	NPD4697	Phase 3
0.6695	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6639	Remote Similarity	NPD6616	Approved
0.6634	Remote Similarity	NPD7515	Phase 2
0.6634	Remote Similarity	NPD7637	Suspended
0.6634	Remote Similarity	NPD8035	Phase 2
0.6634	Remote Similarity	NPD8034	Phase 2
0.661	Remote Similarity	NPD7604	Phase 2
0.66	Remote Similarity	NPD6051	Approved
0.6598	Remote Similarity	NPD4197	Approved
0.6583	Remote Similarity	NPD7078	Approved
0.6581	Remote Similarity	NPD5983	Phase 2
0.6569	Remote Similarity	NPD8171	Discontinued
0.6559	Remote Similarity	NPD6116	Phase 1
0.6552	Remote Similarity	NPD4522	Approved
0.6552	Remote Similarity	NPD7101	Approved
0.6552	Remote Similarity	NPD7100	Approved
0.6545	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7632	Discontinued
0.6535	Remote Similarity	NPD7136	Phase 2
0.6522	Remote Similarity	NPD7115	Discovery
0.6514	Remote Similarity	NPD6008	Approved
0.65	Remote Similarity	NPD6336	Discontinued
0.6491	Remote Similarity	NPD5167	Approved
0.6486	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5281	Approved
0.6471	Remote Similarity	NPD5284	Approved
0.6466	Remote Similarity	NPD6335	Approved
0.6465	Remote Similarity	NPD4688	Approved
0.6465	Remote Similarity	NPD4690	Approved
0.6465	Remote Similarity	NPD4689	Approved
0.6465	Remote Similarity	NPD4693	Phase 3
0.6465	Remote Similarity	NPD5690	Phase 2
0.6465	Remote Similarity	NPD5205	Approved
0.6465	Remote Similarity	NPD4138	Approved
0.6465	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6117	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