NPASS Compound

Structure

CID35171 OpenBabel06191715362D 33 38 0 0 1 0 0 0 0 0999 V2000 4.4513 1.0861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0802 -3.7967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5160 -2.3897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7149 -2.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6248 -1.8746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8126 -1.4057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6517 -2.6850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6242 -4.6869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8124 -4.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4366 -3.2807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8110 -3.2809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7149 -1.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5351 0.8911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2465 -1.8737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6248 -2.8123 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4363 -4.2180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0006 -1.8746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0006 -2.8123 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6231 -2.8120 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1201 -1.8737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4353 -1.4054 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4347 -0.4686 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6231 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8127 -3.2812 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6232 -1.8742 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8116 -1.4057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9080 1.5870 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3087 -4.7218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4956 -3.3157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0569 -1.8737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6517 -1.0625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2459 0.0000 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 13 1 0 0 0 0 3 25 1 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 24 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 31 1 0 0 0 0 13 27 2 0 0 0 0 13 32 1 0 0 0 0 14 21 1 0 0 0 0 15 24 1 1 0 0 0 16 28 1 6 0 0 0 17 18 1 0 0 0 0 17 26 1 1 0 0 0 18 24 1 6 0 0 0 19 25 1 6 0 0 0 19 29 1 0 0 0 0 20 30 2 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 25 1 6 0 0 0 22 23 1 0 0 0 0 22 32 1 6 0 0 0 23 26 1 1 0 0 0 23 33 1 0 0 0 0 24 2 1 6 0 0 0 25 26 1 6 0 0 0 26 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.23
Volume:	457.899
LogP:	2.706
LogD:	2.57
LogS:	-4.441
# Rotatable Bonds:	3
TPSA:	109.5
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	5.409
Fsp3:	0.769
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:	-5.298
MDCK Permeability:	4.065122629981488e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.039
20% Bioavailability (F20%):	0.168
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.267
Plasma Protein Binding (PPB):	79.36808013916016%
Volume Distribution (VD):	1.458
Pgp-substrate:	21.071292877197266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.44
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.298
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.226
CYP3A4-inhibitor:	0.747
CYP3A4-substrate:	0.288

ADMET: Excretion

Clearance (CL):	8.469
Half-life (T1/2):	0.535

ADMET: Toxicity

hERG Blockers:	0.848
Human Hepatotoxicity (H-HT):	0.878
Drug-inuced Liver Injury (DILI):	0.445
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.919
Maximum Recommended Daily Dose:	0.808
Skin Sensitization:	0.313
Carcinogencity:	0.402
Eye Corrosion:	0.333
Eye Irritation:	0.026
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC35171

Natural Product ID:	NPC35171
*Common Name:**	GZNLDYYHFCFJOU-QLKRLITRSA-N
IUPAC Name:	n.a.
Synonyms:	12-Beta-Hydroxycinobufagin; 12Beta-Hydroxycinobufagin
Standard InCHIKey:	GZNLDYYHFCFJOU-QLKRLITRSA-N
Standard InCHI:	InChI=1S/C26H34O7/c1-13(27)32-22-21(14-4-7-20(30)31-12-14)25(3)19(29)11-18-17(26(25)23(22)33-26)6-5-15-10-16(28)8-9-24(15,18)2/h4,7,12,15-19,21-23,28-29H,5-6,8-11H2,1-3H3/t15-,16+,17-,18+,19-,21+,22-,23-,24+,25-,26-/m1/s1
SMILES:	CC(=O)O[C@@H]1[C@H](c2ccc(=O)oc2)[C@@]2(C)[C@@H](C[C@H]3[C@@H](CC[C@@H]4C[C@H](CC[C@]34C)O)[C@]32[C@@H]1O3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517941
PubChem CID:	15513542
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]
NPO20112	Syncephalastrum racemosum	Species	Syncephalastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558746]
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]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20112	Syncephalastrum racemosum	Species	Syncephalastraceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.79	ug.mL-1	PMID[526766]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	0.01	ug.mL-1	PMID[526766]
NPT1366	Cell Line	MH60	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[526766]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	370.0	nM	PMID[526767]

☑ 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 NPC35171 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	1434
0.2-0.3	2946
0.3-0.4	5487
0.4-0.5	10294
0.5-0.6	9892
0.6-0.7	9771
0.7-0.8	2129
0.8-0.85	269
0.85-0.9	37
0.9-0.95	30
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC213761
0.9909	High Similarity	NPC112936
0.9908	High Similarity	NPC16701
0.9818	High Similarity	NPC278681
0.9817	High Similarity	NPC157380
0.9636	High Similarity	NPC185287
0.9541	High Similarity	NPC171126
0.945	High Similarity	NPC44537
0.9298	High Similarity	NPC312481
0.9266	High Similarity	NPC103491
0.9174	High Similarity	NPC75389
0.9138	High Similarity	NPC6193
0.9091	High Similarity	NPC12795
0.9083	High Similarity	NPC275060
0.9083	High Similarity	NPC304276
0.9083	High Similarity	NPC137462
0.8991	High Similarity	NPC79298
0.8991	High Similarity	NPC43063
0.8824	High Similarity	NPC159499
0.8727	High Similarity	NPC295843
0.8718	High Similarity	NPC41123
0.8718	High Similarity	NPC257610
0.8718	High Similarity	NPC145074
0.8718	High Similarity	NPC114939
0.8716	High Similarity	NPC171014
0.8684	High Similarity	NPC154815
0.8684	High Similarity	NPC241977
0.8596	High Similarity	NPC247760
0.8559	High Similarity	NPC220217
0.8559	High Similarity	NPC119855
0.8534	High Similarity	NPC113425
0.8534	High Similarity	NPC232564
0.8509	High Similarity	NPC470076
0.8509	High Similarity	NPC183603
0.8487	Intermediate Similarity	NPC233500
0.8468	Intermediate Similarity	NPC165969
0.8417	Intermediate Similarity	NPC196130
0.839	Intermediate Similarity	NPC146786
0.8378	Intermediate Similarity	NPC187302
0.8378	Intermediate Similarity	NPC189588
0.8378	Intermediate Similarity	NPC196471
0.8378	Intermediate Similarity	NPC97487
0.8378	Intermediate Similarity	NPC10232
0.8347	Intermediate Similarity	NPC55602
0.8319	Intermediate Similarity	NPC219656
0.8319	Intermediate Similarity	NPC153085
0.8319	Intermediate Similarity	NPC268326
0.8306	Intermediate Similarity	NPC221414
0.8305	Intermediate Similarity	NPC290693
0.8291	Intermediate Similarity	NPC216665
0.8264	Intermediate Similarity	NPC471082
0.8264	Intermediate Similarity	NPC115349
0.8261	Intermediate Similarity	NPC16270
0.825	Intermediate Similarity	NPC79579
0.825	Intermediate Similarity	NPC184555
0.823	Intermediate Similarity	NPC265502
0.823	Intermediate Similarity	NPC29389
0.823	Intermediate Similarity	NPC469960
0.823	Intermediate Similarity	NPC93026
0.823	Intermediate Similarity	NPC186668
0.823	Intermediate Similarity	NPC471206
0.822	Intermediate Similarity	NPC470075
0.8217	Intermediate Similarity	NPC75616
0.8214	Intermediate Similarity	NPC472821
0.8214	Intermediate Similarity	NPC160583
0.8211	Intermediate Similarity	NPC179261
0.8198	Intermediate Similarity	NPC295110
0.8198	Intermediate Similarity	NPC268829
0.8198	Intermediate Similarity	NPC247701
0.8198	Intermediate Similarity	NPC222875
0.8198	Intermediate Similarity	NPC25177
0.8197	Intermediate Similarity	NPC219804
0.819	Intermediate Similarity	NPC71680
0.8182	Intermediate Similarity	NPC278673
0.8182	Intermediate Similarity	NPC67569
0.8174	Intermediate Similarity	NPC475030
0.8167	Intermediate Similarity	NPC5883
0.8167	Intermediate Similarity	NPC44899
0.8167	Intermediate Similarity	NPC305260
0.8167	Intermediate Similarity	NPC304260
0.8167	Intermediate Similarity	NPC29639
0.8167	Intermediate Similarity	NPC270850
0.8165	Intermediate Similarity	NPC299654
0.8158	Intermediate Similarity	NPC469959
0.8158	Intermediate Similarity	NPC469957
0.8158	Intermediate Similarity	NPC108682
0.8158	Intermediate Similarity	NPC472263
0.8151	Intermediate Similarity	NPC471351
0.8151	Intermediate Similarity	NPC243196
0.8151	Intermediate Similarity	NPC471355
0.8151	Intermediate Similarity	NPC77319
0.8151	Intermediate Similarity	NPC84987
0.8151	Intermediate Similarity	NPC34390
0.8151	Intermediate Similarity	NPC27507
0.8151	Intermediate Similarity	NPC158344
0.8151	Intermediate Similarity	NPC244402
0.8151	Intermediate Similarity	NPC309034
0.8151	Intermediate Similarity	NPC99728
0.8151	Intermediate Similarity	NPC50305
0.8151	Intermediate Similarity	NPC87250
0.8151	Intermediate Similarity	NPC471354
0.8151	Intermediate Similarity	NPC471353
0.8151	Intermediate Similarity	NPC142066
0.8151	Intermediate Similarity	NPC196429
0.8151	Intermediate Similarity	NPC157376
0.8151	Intermediate Similarity	NPC474418
0.8151	Intermediate Similarity	NPC473852
0.8142	Intermediate Similarity	NPC472822
0.8136	Intermediate Similarity	NPC43213
0.8136	Intermediate Similarity	NPC84949
0.8136	Intermediate Similarity	NPC31354
0.8136	Intermediate Similarity	NPC69576
0.8136	Intermediate Similarity	NPC471633
0.813	Intermediate Similarity	NPC8374
0.8125	Intermediate Similarity	NPC470972
0.812	Intermediate Similarity	NPC150228
0.812	Intermediate Similarity	NPC214005
0.8115	Intermediate Similarity	NPC470265
0.8115	Intermediate Similarity	NPC23786
0.8103	Intermediate Similarity	NPC15551
0.8103	Intermediate Similarity	NPC177047
0.8099	Intermediate Similarity	NPC474370
0.8087	Intermediate Similarity	NPC50124
0.8083	Intermediate Similarity	NPC83287
0.8083	Intermediate Similarity	NPC153440
0.807	Intermediate Similarity	NPC470980
0.8067	Intermediate Similarity	NPC199428
0.8067	Intermediate Similarity	NPC298278
0.8067	Intermediate Similarity	NPC5311
0.8067	Intermediate Similarity	NPC310341
0.8067	Intermediate Similarity	NPC99620
0.8067	Intermediate Similarity	NPC193382
0.8065	Intermediate Similarity	NPC293112
0.8062	Intermediate Similarity	NPC62172
0.8062	Intermediate Similarity	NPC289700
0.8053	Intermediate Similarity	NPC45897
0.8053	Intermediate Similarity	NPC297617
0.8051	Intermediate Similarity	NPC73050
0.8049	Intermediate Similarity	NPC11895
0.8049	Intermediate Similarity	NPC469789
0.8036	Intermediate Similarity	NPC475617
0.8034	Intermediate Similarity	NPC262083
0.8034	Intermediate Similarity	NPC255401
0.8034	Intermediate Similarity	NPC471484
0.8034	Intermediate Similarity	NPC284162
0.8033	Intermediate Similarity	NPC475219
0.8033	Intermediate Similarity	NPC231518
0.8017	Intermediate Similarity	NPC5292
0.8017	Intermediate Similarity	NPC264954
0.8	Intermediate Similarity	NPC475781
0.8	Intermediate Similarity	NPC203862
0.8	Intermediate Similarity	NPC472820
0.8	Intermediate Similarity	NPC152615
0.8	Intermediate Similarity	NPC93883
0.7984	Intermediate Similarity	NPC81736
0.7984	Intermediate Similarity	NPC172154
0.7984	Intermediate Similarity	NPC158350
0.7983	Intermediate Similarity	NPC265290
0.7983	Intermediate Similarity	NPC305044
0.7982	Intermediate Similarity	NPC473543
0.7982	Intermediate Similarity	NPC200861
0.7982	Intermediate Similarity	NPC3359
0.7967	Intermediate Similarity	NPC153700
0.7967	Intermediate Similarity	NPC193893
0.7967	Intermediate Similarity	NPC88326
0.7967	Intermediate Similarity	NPC170538
0.7967	Intermediate Similarity	NPC107493
0.7966	Intermediate Similarity	NPC241477
0.7965	Intermediate Similarity	NPC11956
0.7965	Intermediate Similarity	NPC475344
0.7965	Intermediate Similarity	NPC476471
0.7951	Intermediate Similarity	NPC475629
0.7951	Intermediate Similarity	NPC475556
0.7951	Intermediate Similarity	NPC474466
0.7951	Intermediate Similarity	NPC475136
0.7951	Intermediate Similarity	NPC474585
0.7949	Intermediate Similarity	NPC472214
0.7949	Intermediate Similarity	NPC238850
0.7949	Intermediate Similarity	NPC472215
0.7946	Intermediate Similarity	NPC98813
0.7946	Intermediate Similarity	NPC13743
0.7946	Intermediate Similarity	NPC79631
0.7946	Intermediate Similarity	NPC38855
0.7934	Intermediate Similarity	NPC50774
0.7934	Intermediate Similarity	NPC709
0.7934	Intermediate Similarity	NPC472080
0.7928	Intermediate Similarity	NPC51499
0.792	Intermediate Similarity	NPC473635
0.7917	Intermediate Similarity	NPC190286
0.7913	Intermediate Similarity	NPC189863
0.7913	Intermediate Similarity	NPC472818
0.7913	Intermediate Similarity	NPC266570
0.7909	Intermediate Similarity	NPC276110
0.7907	Intermediate Similarity	NPC248703
0.7903	Intermediate Similarity	NPC473979
0.7899	Intermediate Similarity	NPC101400
0.7899	Intermediate Similarity	NPC101965
0.7895	Intermediate Similarity	NPC23584
0.7895	Intermediate Similarity	NPC473523
0.7895	Intermediate Similarity	NPC474124

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 NPC35171 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	879
0.2-0.3	1753
0.3-0.4	2662
0.4-0.5	2144
0.5-0.6	1011
0.6-0.7	339
0.7-0.8	25
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
0.8487	Intermediate Similarity	NPD7503	Approved
0.8083	Intermediate Similarity	NPD7327	Approved
0.8083	Intermediate Similarity	NPD7328	Approved
0.8033	Intermediate Similarity	NPD8033	Approved
0.8017	Intermediate Similarity	NPD7516	Approved
0.7886	Intermediate Similarity	NPD8378	Approved
0.7886	Intermediate Similarity	NPD8296	Approved
0.7886	Intermediate Similarity	NPD8380	Approved
0.7886	Intermediate Similarity	NPD8335	Approved
0.7886	Intermediate Similarity	NPD8379	Approved
0.7857	Intermediate Similarity	NPD7638	Approved
0.7851	Intermediate Similarity	NPD7115	Discovery
0.7805	Intermediate Similarity	NPD8294	Approved
0.7805	Intermediate Similarity	NPD8377	Approved
0.7788	Intermediate Similarity	NPD7640	Approved
0.7788	Intermediate Similarity	NPD7639	Approved
0.7632	Intermediate Similarity	NPD6648	Approved
0.7565	Intermediate Similarity	NPD5344	Discontinued
0.75	Intermediate Similarity	NPD7507	Approved
0.7462	Intermediate Similarity	NPD7319	Approved
0.7377	Intermediate Similarity	NPD6053	Discontinued
0.7273	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD7736	Approved
0.7244	Intermediate Similarity	NPD6319	Approved
0.7236	Intermediate Similarity	NPD8297	Approved
0.7203	Intermediate Similarity	NPD7632	Discontinued
0.719	Intermediate Similarity	NPD6899	Approved
0.719	Intermediate Similarity	NPD6881	Approved
0.7177	Intermediate Similarity	NPD4632	Approved
0.7154	Intermediate Similarity	NPD7492	Approved
0.7109	Intermediate Similarity	NPD6054	Approved
0.7107	Intermediate Similarity	NPD5697	Approved
0.7099	Intermediate Similarity	NPD6616	Approved
0.7094	Intermediate Similarity	NPD4225	Approved
0.708	Intermediate Similarity	NPD7838	Discovery
0.7077	Intermediate Similarity	NPD7604	Phase 2
0.7073	Intermediate Similarity	NPD6883	Approved
0.7073	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7102	Approved
0.7073	Intermediate Similarity	NPD7290	Approved
0.7045	Intermediate Similarity	NPD7078	Approved
0.7025	Intermediate Similarity	NPD7128	Approved
0.7025	Intermediate Similarity	NPD6008	Approved
0.7025	Intermediate Similarity	NPD5739	Approved
0.7025	Intermediate Similarity	NPD6675	Approved
0.7025	Intermediate Similarity	NPD6402	Approved
0.7018	Intermediate Similarity	NPD7637	Suspended
0.7016	Intermediate Similarity	NPD8130	Phase 1
0.7016	Intermediate Similarity	NPD6847	Approved
0.7016	Intermediate Similarity	NPD6649	Approved
0.7016	Intermediate Similarity	NPD6617	Approved
0.7016	Intermediate Similarity	NPD6650	Approved
0.7016	Intermediate Similarity	NPD6869	Approved
0.7008	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD6370	Approved
0.7	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6013	Approved
0.6992	Remote Similarity	NPD6014	Approved
0.6992	Remote Similarity	NPD6012	Approved
0.6964	Remote Similarity	NPD7524	Approved
0.696	Remote Similarity	NPD6882	Approved
0.6923	Remote Similarity	NPD5983	Phase 2
0.6923	Remote Similarity	NPD6016	Approved
0.6923	Remote Similarity	NPD6015	Approved
0.6911	Remote Similarity	NPD6011	Approved
0.6911	Remote Similarity	NPD7320	Approved
0.6911	Remote Similarity	NPD6686	Approved
0.6909	Remote Similarity	NPD6695	Phase 3
0.687	Remote Similarity	NPD5988	Approved
0.6855	Remote Similarity	NPD6372	Approved
0.6855	Remote Similarity	NPD6373	Approved
0.6846	Remote Similarity	NPD6059	Approved
0.6842	Remote Similarity	NPD6051	Approved
0.6842	Remote Similarity	NPD6336	Discontinued
0.6833	Remote Similarity	NPD4159	Approved
0.6829	Remote Similarity	NPD5701	Approved
0.6829	Remote Similarity	NPD6412	Phase 2
0.6829	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4634	Approved
0.6791	Remote Similarity	NPD8293	Discontinued
0.6789	Remote Similarity	NPD7525	Registered
0.6777	Remote Similarity	NPD5211	Phase 2
0.6772	Remote Similarity	NPD8133	Approved
0.675	Remote Similarity	NPD5285	Approved
0.675	Remote Similarity	NPD5286	Approved
0.675	Remote Similarity	NPD4696	Approved
0.6723	Remote Similarity	NPD6084	Phase 2
0.6723	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD6371	Approved
0.6641	Remote Similarity	NPD7101	Approved
0.6641	Remote Similarity	NPD7100	Approved
0.6639	Remote Similarity	NPD4633	Approved
0.6639	Remote Similarity	NPD5226	Approved
0.6639	Remote Similarity	NPD5224	Approved
0.6639	Remote Similarity	NPD5225	Approved
0.6636	Remote Similarity	NPD6930	Phase 2
0.6636	Remote Similarity	NPD7514	Phase 3
0.6636	Remote Similarity	NPD6931	Approved
0.6614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5174	Approved
0.6585	Remote Similarity	NPD5175	Approved
0.6583	Remote Similarity	NPD4755	Approved
0.6577	Remote Similarity	NPD6902	Approved
0.6565	Remote Similarity	NPD6335	Approved
0.6557	Remote Similarity	NPD5223	Approved
0.6545	Remote Similarity	NPD6929	Approved
0.6538	Remote Similarity	NPD6274	Approved
0.6529	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6399	Phase 3
0.6525	Remote Similarity	NPD4202	Approved
0.6522	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4250	Approved
0.6522	Remote Similarity	NPD4251	Approved
0.6514	Remote Similarity	NPD6932	Approved
0.6508	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD46	Approved
0.6496	Remote Similarity	NPD6698	Approved
0.6489	Remote Similarity	NPD6317	Approved
0.6486	Remote Similarity	NPD7332	Phase 2
0.6475	Remote Similarity	NPD7260	Phase 2
0.6475	Remote Similarity	NPD4700	Approved
0.6471	Remote Similarity	NPD7748	Approved
0.6466	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7145	Approved
0.6446	Remote Similarity	NPD7902	Approved
0.6443	Remote Similarity	NPD7236	Approved
0.6441	Remote Similarity	NPD6079	Approved
0.6441	Remote Similarity	NPD8035	Phase 2
0.6441	Remote Similarity	NPD5284	Approved
0.6441	Remote Similarity	NPD7515	Phase 2
0.6441	Remote Similarity	NPD7087	Discontinued
0.6441	Remote Similarity	NPD5281	Approved
0.6441	Remote Similarity	NPD8034	Phase 2
0.6439	Remote Similarity	NPD6314	Approved
0.6439	Remote Similarity	NPD6313	Approved
0.6435	Remote Similarity	NPD4249	Approved
0.6419	Remote Similarity	NPD7625	Phase 1
0.6418	Remote Similarity	NPD8513	Phase 3
0.6417	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5695	Phase 3
0.6396	Remote Similarity	NPD4195	Approved
0.6393	Remote Similarity	NPD5696	Approved
0.6378	Remote Similarity	NPD4730	Approved
0.6378	Remote Similarity	NPD4729	Approved
0.6377	Remote Similarity	NPD6033	Approved
0.6364	Remote Similarity	NPD6925	Approved
0.6364	Remote Similarity	NPD5776	Phase 2
0.6348	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6893	Approved
0.6324	Remote Similarity	NPD6067	Discontinued
0.6303	Remote Similarity	NPD5693	Phase 1
0.6299	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6908	Approved
0.6296	Remote Similarity	NPD8515	Approved
0.6296	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD8516	Approved
0.6296	Remote Similarity	NPD6909	Approved
0.6296	Remote Similarity	NPD8517	Approved
0.6293	Remote Similarity	NPD7146	Approved
0.6293	Remote Similarity	NPD6409	Approved
0.6293	Remote Similarity	NPD7334	Approved
0.6293	Remote Similarity	NPD5330	Approved
0.6293	Remote Similarity	NPD7521	Approved
0.6293	Remote Similarity	NPD6684	Approved
0.6281	Remote Similarity	NPD5210	Approved
0.6281	Remote Similarity	NPD4629	Approved
0.6279	Remote Similarity	NPD5250	Approved
0.6279	Remote Similarity	NPD5249	Phase 3
0.6279	Remote Similarity	NPD5247	Approved
0.6279	Remote Similarity	NPD5251	Approved
0.6279	Remote Similarity	NPD5248	Approved
0.6273	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6933	Approved
0.6271	Remote Similarity	NPD5328	Approved
0.6271	Remote Similarity	NPD4753	Phase 2
0.625	Remote Similarity	NPD7645	Phase 2
0.625	Remote Similarity	NPD5128	Approved
0.625	Remote Similarity	NPD6683	Phase 2
0.6239	Remote Similarity	NPD6924	Approved
0.6239	Remote Similarity	NPD6926	Approved
0.6234	Remote Similarity	NPD7239	Suspended
0.6231	Remote Similarity	NPD5215	Approved
0.6231	Remote Similarity	NPD5216	Approved
0.6231	Remote Similarity	NPD5217	Approved
0.623	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5222	Approved
0.623	Remote Similarity	NPD5221	Approved
0.6222	Remote Similarity	NPD7741	Discontinued
0.622	Remote Similarity	NPD4767	Approved
0.622	Remote Similarity	NPD7799	Discontinued
0.622	Remote Similarity	NPD4768	Approved
0.6218	Remote Similarity	NPD5785	Approved
0.6204	Remote Similarity	NPD8328	Phase 3
0.6198	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7900	Approved
0.6195	Remote Similarity	NPD4822	Approved
0.6195	Remote Similarity	NPD4821	Approved
0.6195	Remote Similarity	NPD4819	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