NPASS Compound

Structure

CID159499 OpenBabel06191715532D 30 35 0 0 1 0 0 0 0 0999 V2000 -2.5091 2.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7053 2.6791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6213 1.8695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8111 1.4020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6398 2.6791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6217 4.6748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8080 3.2730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6183 2.8056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8117 4.2078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4316 3.2719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7053 1.0606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0021 3.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2381 1.8699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6216 2.8049 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4316 4.2069 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0014 2.8054 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0011 1.8699 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1070 1.8699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4288 1.4026 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4286 0.4682 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6191 0.0005 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6186 1.8701 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8117 3.2729 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8091 1.4024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2865 4.6299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2977 4.7067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0415 1.8699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2947 -0.0317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6398 1.0606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 5 2 0 0 0 0 2 13 1 0 0 0 0 3 4 1 0 0 0 0 3 14 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 13 2 0 0 0 0 11 29 1 0 0 0 0 12 25 2 0 0 0 0 13 19 1 0 0 0 0 14 23 1 1 0 0 0 15 26 1 6 0 0 0 16 17 1 0 0 0 0 16 23 1 6 0 0 0 17 24 1 1 0 0 0 18 27 2 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 19 22 1 6 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 24 1 0 0 0 0 21 30 1 0 0 0 0 22 24 1 6 0 0 0 23 12 1 6 0 0 0 24 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.2
Volume:	414.517
LogP:	1.544
LogD:	1.667
LogS:	-3.748
# Rotatable Bonds:	2
TPSA:	100.27
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	5.45
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.909
MDCK Permeability:	3.281016324763186e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.927
Plasma Protein Binding (PPB):	65.19609832763672%
Volume Distribution (VD):	1.513
Pgp-substrate:	24.90318489074707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.52
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.439
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.846
CYP3A4-substrate:	0.208

ADMET: Excretion

Clearance (CL):	10.844
Half-life (T1/2):	0.305

ADMET: Toxicity

hERG Blockers:	0.655
Human Hepatotoxicity (H-HT):	0.606
Drug-inuced Liver Injury (DILI):	0.134
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.81
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.55
Carcinogencity:	0.529
Eye Corrosion:	0.043
Eye Irritation:	0.059
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC159499

Natural Product ID:	NPC159499
*Common Name:**	JNBBHUNHDKWCIR-GZQUNXGISA-N
IUPAC Name:	n.a.
Synonyms:	19-Oxodesacetylcinobufagin
Standard InCHIKey:	JNBBHUNHDKWCIR-GZQUNXGISA-N
Standard InCHI:	InChI=1S/C24H30O6/c1-22-8-7-16-17(4-3-14-10-15(26)6-9-23(14,16)12-25)24(22)21(30-24)20(28)19(22)13-2-5-18(27)29-11-13/h2,5,11-12,14-17,19-21,26,28H,3-4,6-10H2,1H3/t14-,15+,16+,17-,19+,20-,21?,22-,23-,24-/m1/s1
SMILES:	O=C[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2([C@]31OC3[C@@H]([C@@H]2c1ccc(=O)oc1)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458384
PubChem CID:	44567217
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001557] Bufanolides 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
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575946]
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141860]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	venom	n.a.	n.a.	PMID[24050254]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28256122]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	9

Activity Type	# Activity
Cell Line	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.65	ug.mL-1	PMID[486422]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3.0	ug.mL-1	PMID[486422]
NPT1366	Cell Line	MH60	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[486422]
NPT1081	Cell Line	BXPC-3	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[486422]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[486422]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[486422]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[486422]
NPT575	Cell Line	KM-20L2	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[486422]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[486422]

☑ 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 NPC159499 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	391
0.1-0.2	1419
0.2-0.3	2930
0.3-0.4	5428
0.4-0.5	10162
0.5-0.6	10121
0.6-0.7	9764
0.7-0.8	2117
0.8-0.85	282
0.85-0.9	37
0.9-0.95	30
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.916	High Similarity	NPC6193
0.9138	High Similarity	NPC185287
0.8983	High Similarity	NPC278681
0.8974	High Similarity	NPC157380
0.8908	High Similarity	NPC112936
0.8898	High Similarity	NPC16701
0.8879	High Similarity	NPC73050
0.8833	High Similarity	NPC312481
0.8824	High Similarity	NPC35171
0.8824	High Similarity	NPC213761
0.875	High Similarity	NPC184555
0.8729	High Similarity	NPC298278
0.8689	High Similarity	NPC55602
0.8682	High Similarity	NPC75616
0.8595	High Similarity	NPC79579
0.8594	High Similarity	NPC158350
0.8534	High Similarity	NPC75389
0.8527	High Similarity	NPC62172
0.8527	High Similarity	NPC289700
0.8512	High Similarity	NPC270850
0.8512	High Similarity	NPC305260
0.8504	High Similarity	NPC155529
0.8492	Intermediate Similarity	NPC221414
0.8475	Intermediate Similarity	NPC44537
0.8462	Intermediate Similarity	NPC16270
0.8448	Intermediate Similarity	NPC275060
0.8443	Intermediate Similarity	NPC145074
0.8443	Intermediate Similarity	NPC474370
0.8443	Intermediate Similarity	NPC41123
0.8443	Intermediate Similarity	NPC114939
0.843	Intermediate Similarity	NPC153440
0.8403	Intermediate Similarity	NPC171126
0.8387	Intermediate Similarity	NPC469789
0.8362	Intermediate Similarity	NPC43063
0.8362	Intermediate Similarity	NPC79298
0.8361	Intermediate Similarity	NPC264954
0.8361	Intermediate Similarity	NPC5292
0.832	Intermediate Similarity	NPC233041
0.832	Intermediate Similarity	NPC8374
0.8306	Intermediate Similarity	NPC153700
0.8306	Intermediate Similarity	NPC88326
0.8306	Intermediate Similarity	NPC107493
0.8305	Intermediate Similarity	NPC103491
0.8293	Intermediate Similarity	NPC474585
0.8279	Intermediate Similarity	NPC50774
0.8279	Intermediate Similarity	NPC146786
0.8279	Intermediate Similarity	NPC709
0.8264	Intermediate Similarity	NPC190286
0.8254	Intermediate Similarity	NPC293112
0.8244	Intermediate Similarity	NPC127656
0.824	Intermediate Similarity	NPC11895
0.824	Intermediate Similarity	NPC473979
0.8231	Intermediate Similarity	NPC248703
0.8226	Intermediate Similarity	NPC67569
0.8226	Intermediate Similarity	NPC46570
0.8211	Intermediate Similarity	NPC61520
0.8211	Intermediate Similarity	NPC475041
0.8197	Intermediate Similarity	NPC470492
0.8197	Intermediate Similarity	NPC167606
0.8197	Intermediate Similarity	NPC286528
0.8197	Intermediate Similarity	NPC140055
0.8197	Intermediate Similarity	NPC20302
0.8175	Intermediate Similarity	NPC8369
0.8175	Intermediate Similarity	NPC81736
0.8175	Intermediate Similarity	NPC172154
0.8167	Intermediate Similarity	NPC476163
0.816	Intermediate Similarity	NPC170538
0.816	Intermediate Similarity	NPC23786
0.816	Intermediate Similarity	NPC470265
0.8151	Intermediate Similarity	NPC12795
0.8136	Intermediate Similarity	NPC472825
0.8136	Intermediate Similarity	NPC304276
0.8136	Intermediate Similarity	NPC137462
0.813	Intermediate Similarity	NPC329736
0.812	Intermediate Similarity	NPC189863
0.812	Intermediate Similarity	NPC295843
0.812	Intermediate Similarity	NPC266570
0.8115	Intermediate Similarity	NPC196931
0.811	Intermediate Similarity	NPC250556
0.811	Intermediate Similarity	NPC469750
0.811	Intermediate Similarity	NPC473635
0.8103	Intermediate Similarity	NPC171014
0.8099	Intermediate Similarity	NPC475966
0.8099	Intermediate Similarity	NPC241977
0.8062	Intermediate Similarity	NPC231529
0.8049	Intermediate Similarity	NPC478204
0.8049	Intermediate Similarity	NPC470493
0.8049	Intermediate Similarity	NPC312824
0.8049	Intermediate Similarity	NPC183580
0.8047	Intermediate Similarity	NPC287423
0.8047	Intermediate Similarity	NPC471356
0.8047	Intermediate Similarity	NPC179412
0.8034	Intermediate Similarity	NPC165969
0.8033	Intermediate Similarity	NPC284915
0.8031	Intermediate Similarity	NPC469790
0.8016	Intermediate Similarity	NPC269642
0.8015	Intermediate Similarity	NPC157817
0.8015	Intermediate Similarity	NPC104585
0.8015	Intermediate Similarity	NPC225385
0.8015	Intermediate Similarity	NPC298783
0.8	Intermediate Similarity	NPC251226
0.8	Intermediate Similarity	NPC478211
0.8	Intermediate Similarity	NPC268530
0.8	Intermediate Similarity	NPC154491
0.7984	Intermediate Similarity	NPC478205
0.7984	Intermediate Similarity	NPC311554
0.7984	Intermediate Similarity	NPC186525
0.7984	Intermediate Similarity	NPC257457
0.7984	Intermediate Similarity	NPC108581
0.7984	Intermediate Similarity	NPC284707
0.7984	Intermediate Similarity	NPC478206
0.7983	Intermediate Similarity	NPC177064
0.7967	Intermediate Similarity	NPC469794
0.7967	Intermediate Similarity	NPC176840
0.7967	Intermediate Similarity	NPC72772
0.7967	Intermediate Similarity	NPC270929
0.7953	Intermediate Similarity	NPC27363
0.7953	Intermediate Similarity	NPC204812
0.7951	Intermediate Similarity	NPC122056
0.7939	Intermediate Similarity	NPC42670
0.7939	Intermediate Similarity	NPC19124
0.7937	Intermediate Similarity	NPC473256
0.7937	Intermediate Similarity	NPC470878
0.7937	Intermediate Similarity	NPC4021
0.7937	Intermediate Similarity	NPC159456
0.7934	Intermediate Similarity	NPC474846
0.7934	Intermediate Similarity	NPC469656
0.7934	Intermediate Similarity	NPC132790
0.7934	Intermediate Similarity	NPC247031
0.7934	Intermediate Similarity	NPC469655
0.7934	Intermediate Similarity	NPC97939
0.7934	Intermediate Similarity	NPC100329
0.7934	Intermediate Similarity	NPC470076
0.7923	Intermediate Similarity	NPC471360
0.7923	Intermediate Similarity	NPC232785
0.7923	Intermediate Similarity	NPC470880
0.7923	Intermediate Similarity	NPC197707
0.7923	Intermediate Similarity	NPC276838
0.7923	Intermediate Similarity	NPC6108
0.7923	Intermediate Similarity	NPC469752
0.7923	Intermediate Similarity	NPC188234
0.7923	Intermediate Similarity	NPC471358
0.7923	Intermediate Similarity	NPC140092
0.7923	Intermediate Similarity	NPC70542
0.7923	Intermediate Similarity	NPC329986
0.7923	Intermediate Similarity	NPC86159
0.7923	Intermediate Similarity	NPC469753
0.7923	Intermediate Similarity	NPC125077
0.7923	Intermediate Similarity	NPC471359
0.7923	Intermediate Similarity	NPC469751
0.7923	Intermediate Similarity	NPC251866
0.7923	Intermediate Similarity	NPC469755
0.7923	Intermediate Similarity	NPC469754
0.7923	Intermediate Similarity	NPC471361
0.7923	Intermediate Similarity	NPC180079
0.7923	Intermediate Similarity	NPC471352
0.7923	Intermediate Similarity	NPC284406
0.7923	Intermediate Similarity	NPC219085
0.7923	Intermediate Similarity	NPC89514
0.7923	Intermediate Similarity	NPC17896
0.7923	Intermediate Similarity	NPC10823
0.7923	Intermediate Similarity	NPC9499
0.792	Intermediate Similarity	NPC473203
0.792	Intermediate Similarity	NPC472667
0.792	Intermediate Similarity	NPC42673
0.7917	Intermediate Similarity	NPC475065
0.7917	Intermediate Similarity	NPC284828
0.7917	Intermediate Similarity	NPC173905
0.7917	Intermediate Similarity	NPC478210
0.7917	Intermediate Similarity	NPC472216
0.7917	Intermediate Similarity	NPC5475
0.7907	Intermediate Similarity	NPC473253
0.7903	Intermediate Similarity	NPC98249
0.7903	Intermediate Similarity	NPC53396
0.7903	Intermediate Similarity	NPC474518
0.7899	Intermediate Similarity	NPC144459
0.7899	Intermediate Similarity	NPC329048
0.7899	Intermediate Similarity	NPC330011
0.7891	Intermediate Similarity	NPC3381
0.7891	Intermediate Similarity	NPC32868
0.7891	Intermediate Similarity	NPC241456
0.7886	Intermediate Similarity	NPC265290
0.7886	Intermediate Similarity	NPC147912
0.7886	Intermediate Similarity	NPC67259
0.7886	Intermediate Similarity	NPC305044
0.7879	Intermediate Similarity	NPC142756
0.7869	Intermediate Similarity	NPC191620
0.7869	Intermediate Similarity	NPC470063
0.7863	Intermediate Similarity	NPC16569
0.7863	Intermediate Similarity	NPC253456
0.7863	Intermediate Similarity	NPC173347
0.7863	Intermediate Similarity	NPC159338
0.7857	Intermediate Similarity	NPC143755
0.7851	Intermediate Similarity	NPC6206
0.7851	Intermediate Similarity	NPC37116
0.7851	Intermediate Similarity	NPC41551
0.7846	Intermediate Similarity	NPC473888
0.7833	Intermediate Similarity	NPC318363
0.7833	Intermediate Similarity	NPC475418
0.7833	Intermediate Similarity	NPC473482

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 NPC159499 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	855
0.2-0.3	1770
0.3-0.4	2662
0.4-0.5	2137
0.5-0.6	1018
0.6-0.7	346
0.7-0.8	26
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8197	Intermediate Similarity	NPD7115	Discovery
0.811	Intermediate Similarity	NPD7507	Approved
0.7923	Intermediate Similarity	NPD7319	Approved
0.7795	Intermediate Similarity	NPD7503	Approved
0.775	Intermediate Similarity	NPD5697	Approved
0.7724	Intermediate Similarity	NPD8297	Approved
0.7717	Intermediate Similarity	NPD6319	Approved
0.7686	Intermediate Similarity	NPD6899	Approved
0.7686	Intermediate Similarity	NPD6881	Approved
0.7661	Intermediate Similarity	NPD4632	Approved
0.7623	Intermediate Similarity	NPD6014	Approved
0.7623	Intermediate Similarity	NPD6013	Approved
0.7623	Intermediate Similarity	NPD6012	Approved
0.7581	Intermediate Similarity	NPD6053	Discontinued
0.7561	Intermediate Similarity	NPD7102	Approved
0.7561	Intermediate Similarity	NPD7290	Approved
0.7561	Intermediate Similarity	NPD6883	Approved
0.7541	Intermediate Similarity	NPD6011	Approved
0.7521	Intermediate Similarity	NPD7128	Approved
0.7521	Intermediate Similarity	NPD6402	Approved
0.7521	Intermediate Similarity	NPD5739	Approved
0.7521	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD6617	Approved
0.7459	Intermediate Similarity	NPD5701	Approved
0.7458	Intermediate Similarity	NPD7638	Approved
0.7444	Intermediate Similarity	NPD7736	Approved
0.744	Intermediate Similarity	NPD6882	Approved
0.7419	Intermediate Similarity	NPD4634	Approved
0.7417	Intermediate Similarity	NPD5211	Phase 2
0.7398	Intermediate Similarity	NPD7320	Approved
0.7395	Intermediate Similarity	NPD7639	Approved
0.7395	Intermediate Similarity	NPD5285	Approved
0.7395	Intermediate Similarity	NPD4696	Approved
0.7395	Intermediate Similarity	NPD5286	Approved
0.7395	Intermediate Similarity	NPD7640	Approved
0.7385	Intermediate Similarity	NPD8033	Approved
0.7377	Intermediate Similarity	NPD6008	Approved
0.7348	Intermediate Similarity	NPD7492	Approved
0.7344	Intermediate Similarity	NPD6009	Approved
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6372	Approved
0.7308	Intermediate Similarity	NPD6054	Approved
0.7295	Intermediate Similarity	NPD5141	Approved
0.7293	Intermediate Similarity	NPD6616	Approved
0.7287	Intermediate Similarity	NPD7327	Approved
0.7287	Intermediate Similarity	NPD7328	Approved
0.7273	Intermediate Similarity	NPD4633	Approved
0.7273	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD5224	Approved
0.7273	Intermediate Similarity	NPD5225	Approved
0.7273	Intermediate Similarity	NPD7604	Phase 2
0.7252	Intermediate Similarity	NPD6016	Approved
0.7252	Intermediate Similarity	NPD5983	Phase 2
0.7252	Intermediate Similarity	NPD6015	Approved
0.7239	Intermediate Similarity	NPD7078	Approved
0.7231	Intermediate Similarity	NPD7516	Approved
0.7227	Intermediate Similarity	NPD4755	Approved
0.7213	Intermediate Similarity	NPD5175	Approved
0.7213	Intermediate Similarity	NPD5174	Approved
0.7197	Intermediate Similarity	NPD6370	Approved
0.7197	Intermediate Similarity	NPD5988	Approved
0.719	Intermediate Similarity	NPD5223	Approved
0.7176	Intermediate Similarity	NPD8377	Approved
0.7176	Intermediate Similarity	NPD8294	Approved
0.7167	Intermediate Similarity	NPD4225	Approved
0.7132	Intermediate Similarity	NPD6274	Approved
0.7121	Intermediate Similarity	NPD8378	Approved
0.7121	Intermediate Similarity	NPD8296	Approved
0.7121	Intermediate Similarity	NPD8380	Approved
0.7121	Intermediate Similarity	NPD8335	Approved
0.7121	Intermediate Similarity	NPD8379	Approved
0.7107	Intermediate Similarity	NPD4700	Approved
0.7099	Intermediate Similarity	NPD7101	Approved
0.7099	Intermediate Similarity	NPD7100	Approved
0.7087	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6317	Approved
0.7045	Intermediate Similarity	NPD6059	Approved
0.7037	Intermediate Similarity	NPD6336	Discontinued
0.7023	Intermediate Similarity	NPD6314	Approved
0.7023	Intermediate Similarity	NPD6335	Approved
0.7023	Intermediate Similarity	NPD6313	Approved
0.7008	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD8293	Discontinued
0.6984	Remote Similarity	NPD4730	Approved
0.6984	Remote Similarity	NPD4729	Approved
0.6984	Remote Similarity	NPD6686	Approved
0.6949	Remote Similarity	NPD6079	Approved
0.6942	Remote Similarity	NPD6084	Phase 2
0.6942	Remote Similarity	NPD6083	Phase 2
0.6905	Remote Similarity	NPD6412	Phase 2
0.6891	Remote Similarity	NPD4202	Approved
0.6875	Remote Similarity	NPD5250	Approved
0.6875	Remote Similarity	NPD5249	Phase 3
0.6875	Remote Similarity	NPD5248	Approved
0.6875	Remote Similarity	NPD5247	Approved
0.6875	Remote Similarity	NPD5251	Approved
0.6866	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5222	Approved
0.686	Remote Similarity	NPD5221	Approved
0.686	Remote Similarity	NPD4697	Phase 3
0.6855	Remote Similarity	NPD7632	Discontinued
0.685	Remote Similarity	NPD5128	Approved
0.6846	Remote Similarity	NPD8133	Approved
0.6846	Remote Similarity	NPD7236	Approved
0.6825	Remote Similarity	NPD4768	Approved
0.6825	Remote Similarity	NPD4767	Approved
0.6822	Remote Similarity	NPD5215	Approved
0.6822	Remote Similarity	NPD5216	Approved
0.6822	Remote Similarity	NPD5217	Approved
0.6807	Remote Similarity	NPD5284	Approved
0.6807	Remote Similarity	NPD5281	Approved
0.6803	Remote Similarity	NPD5173	Approved
0.68	Remote Similarity	NPD4754	Approved
0.678	Remote Similarity	NPD5328	Approved
0.6777	Remote Similarity	NPD5695	Phase 3
0.6774	Remote Similarity	NPD5344	Discontinued
0.6772	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6399	Phase 3
0.6748	Remote Similarity	NPD5696	Approved
0.6744	Remote Similarity	NPD6371	Approved
0.6744	Remote Similarity	NPD5169	Approved
0.6744	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5135	Approved
0.6741	Remote Similarity	NPD8513	Phase 3
0.6741	Remote Similarity	NPD6908	Approved
0.6741	Remote Similarity	NPD6909	Approved
0.6719	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7748	Approved
0.6694	Remote Similarity	NPD6648	Approved
0.6692	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6639	Remote Similarity	NPD4753	Phase 2
0.6639	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4629	Approved
0.6639	Remote Similarity	NPD5210	Approved
0.6623	Remote Similarity	NPD7239	Suspended
0.6618	Remote Similarity	NPD8517	Approved
0.6618	Remote Similarity	NPD8516	Approved
0.6618	Remote Similarity	NPD8515	Approved
0.6617	Remote Similarity	NPD6868	Approved
0.661	Remote Similarity	NPD3573	Approved
0.6583	Remote Similarity	NPD6698	Approved
0.6583	Remote Similarity	NPD46	Approved
0.6583	Remote Similarity	NPD7838	Discovery
0.6581	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6033	Approved
0.6541	Remote Similarity	NPD5167	Approved
0.6529	Remote Similarity	NPD7637	Suspended
0.6529	Remote Similarity	NPD6411	Approved
0.6529	Remote Similarity	NPD5694	Approved
0.6525	Remote Similarity	NPD7521	Approved
0.6525	Remote Similarity	NPD5330	Approved
0.6525	Remote Similarity	NPD6684	Approved
0.6525	Remote Similarity	NPD7146	Approved
0.6525	Remote Similarity	NPD7334	Approved
0.6525	Remote Similarity	NPD3618	Phase 1
0.6525	Remote Similarity	NPD6409	Approved
0.6522	Remote Similarity	NPD8328	Phase 3
0.6519	Remote Similarity	NPD5761	Phase 2
0.6519	Remote Similarity	NPD5760	Phase 2
0.6508	Remote Similarity	NPD4159	Approved
0.6496	Remote Similarity	NPD3666	Approved
0.6496	Remote Similarity	NPD3665	Phase 1
0.6496	Remote Similarity	NPD3133	Approved
0.6475	Remote Similarity	NPD5779	Approved
0.6475	Remote Similarity	NPD5778	Approved
0.6466	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD5785	Approved
0.6446	Remote Similarity	NPD5692	Phase 3
0.6446	Remote Similarity	NPD5207	Approved
0.6423	Remote Similarity	NPD6001	Approved
0.6423	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7900	Approved
0.6417	Remote Similarity	NPD6903	Approved
0.641	Remote Similarity	NPD4788	Approved
0.6393	Remote Similarity	NPD6050	Approved
0.6386	Remote Similarity	NPD7799	Discontinued
0.6385	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6101	Approved
0.6364	Remote Similarity	NPD6051	Approved
0.6364	Remote Similarity	NPD6673	Approved
0.6364	Remote Similarity	NPD6904	Approved
0.6364	Remote Similarity	NPD6080	Approved
0.6364	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4786	Approved
0.635	Remote Similarity	NPD4522	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