NPASS Compound

Structure

CID216866 OpenBabel06191716002D 40 44 0 0 1 0 0 0 0 0999 V2000 -0.0818 -1.7688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3885 3.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2664 3.4416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5726 0.4709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6945 2.9344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8472 2.4452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3885 0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6934 0.9777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8473 -0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3889 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -1.4665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5418 2.4453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5418 1.4669 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6934 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2352 1.4670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2357 -1.4665 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8473 1.4669 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6946 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8473 -0.4892 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0826 -1.9553 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9293 -1.4663 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9292 -0.4884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2352 2.4453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0823 0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3885 2.9344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9777 0.0000 C 0 0 2 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 -1.6946 0.9778 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3891 -2.9334 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5740 -2.1202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5682 -0.5048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5606 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0827 -2.9332 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7762 -1.9551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7759 0.0006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1013 2.9452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0821 0.9782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2355 -0.4887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 7 8 1 0 0 0 0 7 14 2 0 0 0 0 8 19 1 0 0 0 0 9 15 1 0 0 0 0 9 17 2 0 0 0 0 10 16 1 0 0 0 0 10 28 1 0 0 0 0 11 20 1 0 0 0 0 11 29 1 0 0 0 0 12 31 1 0 0 0 0 13 21 1 0 0 0 0 13 32 2 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 30 1 6 0 0 0 16 21 1 0 0 0 0 16 33 1 1 0 0 0 17 25 1 0 0 0 0 17 39 1 0 0 0 0 18 12 1 6 0 0 0 18 22 1 0 0 0 0 18 40 1 0 0 0 0 19 28 1 1 0 0 0 19 30 1 0 0 0 0 20 30 1 0 0 0 0 20 34 2 0 0 0 0 21 29 1 6 0 0 0 22 23 1 0 0 0 0 22 35 1 1 0 0 0 23 24 1 0 0 0 0 23 36 1 6 0 0 0 24 26 1 0 0 0 0 24 37 1 1 0 0 0 25 27 1 0 0 0 0 25 38 2 0 0 0 0 26 39 1 6 0 0 0 26 40 1 0 0 0 0 28 29 1 1 0 0 0 29 5 1 6 0 0 0 30 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.28
Volume:	559.374
LogP:	0.692
LogD:	0.342
LogS:	-3.688
# Rotatable Bonds:	4
TPSA:	170.82
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	5.645
Fsp3:	0.767
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.168
MDCK Permeability:	8.24362359708175e-06
Pgp-inhibitor:	0.996
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.367
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.303

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	62.26780700683594%
Volume Distribution (VD):	0.628
Pgp-substrate:	20.983163833618164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.608
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.794
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.151
CYP3A4-substrate:	0.372

ADMET: Excretion

Clearance (CL):	2.025
Half-life (T1/2):	0.868

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.217
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.33
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.029
Carcinogencity:	0.73
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.822

Download Data

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

Natural Product: NPC216866

Natural Product ID:	NPC216866
*Common Name:**	Khekadaengoside K
IUPAC Name:	(8S,9R,10R,13R,14S,16R,17R)-17-acetyl-16-hydroxy-4,4,9,13,14-pentamethyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
Synonyms:	Khekadaengoside K
Standard InCHIKey:	ZRNZYSQTUUUEOQ-ZCDXCMHTSA-N
Standard InCHI:	InChI=1S/C30H42O10/c1-13(32)21-16(33)10-28(4)19-8-7-14-15(30(19,6)20(34)11-29(21,28)5)9-17(25(38)27(14,2)3)39-26-24(37)23(36)22(35)18(12-31)40-26/h7,9,15-16,18-19,21-24,26,31,33,35-37H,8,10-12H2,1-6H3/t15-,16-,18-,19+,21+,22-,23+,24-,26-,28+,29-,30+/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC2=C[C@@H]3C(=CC[C@@H]4[C@@]3(C)C(=O)C[C@]3([C@@]4(C)C[C@H]([C@@H]3C(=O)C)O)C)C(C2=O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923791
PubChem CID:	57399249
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO30742	Machilus yaoshansis	Species	Lauraceae	Eukaryota	root	Dayao Mountain, Guangxi, China	2007-DEC	PMID[22044245]
NPO30742	Machilus yaoshansis	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[22044245]
NPO30742	Machilus yaoshansis	Species	Lauraceae	Eukaryota	Roots	n.a.	n.a.	PMID[22779787]

☑ 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	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[482338]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[482338]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[482338]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[482338]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[482338]

☑ 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 NPC216866 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	252
0.1-0.2	1562
0.2-0.3	5326
0.3-0.4	8678
0.4-0.5	11817
0.5-0.6	8024
0.6-0.7	5105
0.7-0.8	1858
0.8-0.85	61
0.85-0.9	6
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC1980
0.9565	High Similarity	NPC238005
0.9565	High Similarity	NPC141196
0.9402	High Similarity	NPC198714
0.9391	High Similarity	NPC42675
0.9292	High Similarity	NPC31797
0.9153	High Similarity	NPC277191
0.9153	High Similarity	NPC190846
0.9076	High Similarity	NPC93368
0.9052	High Similarity	NPC319570
0.9	High Similarity	NPC152091
0.878	High Similarity	NPC213634
0.8678	High Similarity	NPC6615
0.8678	High Similarity	NPC475194
0.8678	High Similarity	NPC7850
0.8618	High Similarity	NPC69273
0.8618	High Similarity	NPC293623
0.8618	High Similarity	NPC168899
0.8596	High Similarity	NPC470257
0.8525	High Similarity	NPC177820
0.8525	High Similarity	NPC30188
0.8487	Intermediate Similarity	NPC176005
0.848	Intermediate Similarity	NPC241008
0.8462	Intermediate Similarity	NPC260665
0.8462	Intermediate Similarity	NPC477944
0.8435	Intermediate Similarity	NPC246205
0.843	Intermediate Similarity	NPC187950
0.843	Intermediate Similarity	NPC278163
0.8421	Intermediate Similarity	NPC43285
0.8421	Intermediate Similarity	NPC58370
0.8374	Intermediate Similarity	NPC469841
0.8374	Intermediate Similarity	NPC469842
0.8362	Intermediate Similarity	NPC114961
0.8362	Intermediate Similarity	NPC27551
0.8306	Intermediate Similarity	NPC47113
0.8306	Intermediate Similarity	NPC174367
0.8305	Intermediate Similarity	NPC73455
0.8305	Intermediate Similarity	NPC200944
0.8293	Intermediate Similarity	NPC476542
0.8279	Intermediate Similarity	NPC202051
0.8264	Intermediate Similarity	NPC258592
0.8264	Intermediate Similarity	NPC178548
0.8264	Intermediate Similarity	NPC473920
0.8235	Intermediate Similarity	NPC74727
0.8235	Intermediate Similarity	NPC116024
0.8235	Intermediate Similarity	NPC471398
0.8235	Intermediate Similarity	NPC473898
0.8226	Intermediate Similarity	NPC130229
0.822	Intermediate Similarity	NPC130427
0.8211	Intermediate Similarity	NPC475431
0.8211	Intermediate Similarity	NPC28532
0.8197	Intermediate Similarity	NPC472257
0.8197	Intermediate Similarity	NPC476849
0.819	Intermediate Similarity	NPC272576
0.819	Intermediate Similarity	NPC473288
0.8182	Intermediate Similarity	NPC475632
0.8182	Intermediate Similarity	NPC86020
0.8175	Intermediate Similarity	NPC295220
0.8175	Intermediate Similarity	NPC475636
0.8175	Intermediate Similarity	NPC311534
0.8175	Intermediate Similarity	NPC245094
0.8174	Intermediate Similarity	NPC162033
0.8174	Intermediate Similarity	NPC210178
0.816	Intermediate Similarity	NPC104427
0.813	Intermediate Similarity	NPC169727
0.813	Intermediate Similarity	NPC476543
0.813	Intermediate Similarity	NPC476545
0.813	Intermediate Similarity	NPC194310
0.813	Intermediate Similarity	NPC131841
0.813	Intermediate Similarity	NPC133506
0.813	Intermediate Similarity	NPC47567
0.813	Intermediate Similarity	NPC258815
0.813	Intermediate Similarity	NPC258789
0.813	Intermediate Similarity	NPC241310
0.813	Intermediate Similarity	NPC412
0.813	Intermediate Similarity	NPC476544
0.813	Intermediate Similarity	NPC475182
0.8125	Intermediate Similarity	NPC147954
0.8125	Intermediate Similarity	NPC471855
0.812	Intermediate Similarity	NPC118225
0.812	Intermediate Similarity	NPC304495
0.8115	Intermediate Similarity	NPC127530
0.8115	Intermediate Similarity	NPC161738
0.8115	Intermediate Similarity	NPC279143
0.811	Intermediate Similarity	NPC54614
0.811	Intermediate Similarity	NPC309096
0.8099	Intermediate Similarity	NPC218970
0.8095	Intermediate Similarity	NPC292290
0.8095	Intermediate Similarity	NPC305496
0.8095	Intermediate Similarity	NPC2757
0.8087	Intermediate Similarity	NPC223741
0.8083	Intermediate Similarity	NPC165439
0.8083	Intermediate Similarity	NPC474557
0.8083	Intermediate Similarity	NPC477580
0.808	Intermediate Similarity	NPC318135
0.808	Intermediate Similarity	NPC473505
0.8067	Intermediate Similarity	NPC205534
0.8065	Intermediate Similarity	NPC131824
0.8065	Intermediate Similarity	NPC471965
0.8065	Intermediate Similarity	NPC313528
0.8062	Intermediate Similarity	NPC475487
0.806	Intermediate Similarity	NPC803
0.8051	Intermediate Similarity	NPC163314
0.8051	Intermediate Similarity	NPC475317
0.8051	Intermediate Similarity	NPC52241
0.8051	Intermediate Similarity	NPC154856
0.8051	Intermediate Similarity	NPC129340
0.8049	Intermediate Similarity	NPC475187
0.8049	Intermediate Similarity	NPC471406
0.8049	Intermediate Similarity	NPC472076
0.8049	Intermediate Similarity	NPC472075
0.8047	Intermediate Similarity	NPC173347
0.8033	Intermediate Similarity	NPC297179
0.8033	Intermediate Similarity	NPC239293
0.8016	Intermediate Similarity	NPC87662
0.8016	Intermediate Similarity	NPC285091
0.8015	Intermediate Similarity	NPC471089
0.8015	Intermediate Similarity	NPC190065
0.8015	Intermediate Similarity	NPC141215
0.8	Intermediate Similarity	NPC228701
0.8	Intermediate Similarity	NPC202666
0.8	Intermediate Similarity	NPC178981
0.8	Intermediate Similarity	NPC471964
0.8	Intermediate Similarity	NPC227397
0.8	Intermediate Similarity	NPC262199
0.8	Intermediate Similarity	NPC14617
0.8	Intermediate Similarity	NPC472077
0.8	Intermediate Similarity	NPC471961
0.8	Intermediate Similarity	NPC194100
0.8	Intermediate Similarity	NPC472078
0.7984	Intermediate Similarity	NPC249553
0.7984	Intermediate Similarity	NPC155529
0.7984	Intermediate Similarity	NPC182900
0.7984	Intermediate Similarity	NPC275675
0.7983	Intermediate Similarity	NPC471243
0.7969	Intermediate Similarity	NPC471407
0.7966	Intermediate Similarity	NPC265655
0.7966	Intermediate Similarity	NPC250018
0.7966	Intermediate Similarity	NPC470615
0.7965	Intermediate Similarity	NPC70733
0.7965	Intermediate Similarity	NPC56071
0.7955	Intermediate Similarity	NPC140045
0.7955	Intermediate Similarity	NPC295885
0.7955	Intermediate Similarity	NPC596
0.7953	Intermediate Similarity	NPC471357
0.7953	Intermediate Similarity	NPC117702
0.7953	Intermediate Similarity	NPC469757
0.7953	Intermediate Similarity	NPC146456
0.7951	Intermediate Similarity	NPC309433
0.7939	Intermediate Similarity	NPC262813
0.7937	Intermediate Similarity	NPC471963
0.7937	Intermediate Similarity	NPC473255
0.7937	Intermediate Similarity	NPC247315
0.7937	Intermediate Similarity	NPC471962
0.7937	Intermediate Similarity	NPC248202
0.7934	Intermediate Similarity	NPC243354
0.7934	Intermediate Similarity	NPC474906
0.7934	Intermediate Similarity	NPC18547
0.7931	Intermediate Similarity	NPC100955
0.7931	Intermediate Similarity	NPC121566
0.792	Intermediate Similarity	NPC156789
0.792	Intermediate Similarity	NPC169816
0.792	Intermediate Similarity	NPC15918
0.792	Intermediate Similarity	NPC94072
0.792	Intermediate Similarity	NPC305771
0.7917	Intermediate Similarity	NPC471245
0.7917	Intermediate Similarity	NPC474265
0.7917	Intermediate Similarity	NPC471244
0.7917	Intermediate Similarity	NPC210420
0.7903	Intermediate Similarity	NPC170814
0.7895	Intermediate Similarity	NPC474720
0.7886	Intermediate Similarity	NPC286347
0.7881	Intermediate Similarity	NPC195708
0.7881	Intermediate Similarity	NPC295389
0.7879	Intermediate Similarity	NPC62172
0.7879	Intermediate Similarity	NPC289700
0.7879	Intermediate Similarity	NPC251998
0.7869	Intermediate Similarity	NPC152199
0.7869	Intermediate Similarity	NPC235539
0.7869	Intermediate Similarity	NPC88945
0.7869	Intermediate Similarity	NPC134869
0.7863	Intermediate Similarity	NPC63023
0.7863	Intermediate Similarity	NPC95243
0.7863	Intermediate Similarity	NPC471234
0.7857	Intermediate Similarity	NPC108141
0.7857	Intermediate Similarity	NPC27363
0.7857	Intermediate Similarity	NPC160084
0.7851	Intermediate Similarity	NPC293038
0.7851	Intermediate Similarity	NPC194273
0.7851	Intermediate Similarity	NPC62696
0.7851	Intermediate Similarity	NPC251309
0.7851	Intermediate Similarity	NPC320118
0.7846	Intermediate Similarity	NPC102316
0.7845	Intermediate Similarity	NPC117185
0.784	Intermediate Similarity	NPC471999
0.784	Intermediate Similarity	NPC46570
0.784	Intermediate Similarity	NPC472000
0.784	Intermediate Similarity	NPC470921
0.7833	Intermediate Similarity	NPC122339
0.7833	Intermediate Similarity	NPC63244

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 NPC216866 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	1858
0.2-0.3	4126
0.3-0.4	1879
0.4-0.5	575
0.5-0.6	254
0.6-0.7	122
0.7-0.8	97
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8584	High Similarity	NPD6412	Phase 2
0.8512	High Similarity	NPD6370	Approved
0.8347	Intermediate Similarity	NPD6054	Approved
0.832	Intermediate Similarity	NPD7736	Approved
0.8197	Intermediate Similarity	NPD6059	Approved
0.813	Intermediate Similarity	NPD6016	Approved
0.813	Intermediate Similarity	NPD6015	Approved
0.8095	Intermediate Similarity	NPD8293	Discontinued
0.808	Intermediate Similarity	NPD7492	Approved
0.8065	Intermediate Similarity	NPD5988	Approved
0.8049	Intermediate Similarity	NPD6319	Approved
0.8016	Intermediate Similarity	NPD6616	Approved
0.8	Intermediate Similarity	NPD8328	Phase 3
0.7953	Intermediate Similarity	NPD7078	Approved
0.7917	Intermediate Similarity	NPD6882	Approved
0.7829	Intermediate Similarity	NPD7319	Approved
0.7805	Intermediate Similarity	NPD6009	Approved
0.7769	Intermediate Similarity	NPD8297	Approved
0.7734	Intermediate Similarity	NPD7507	Approved
0.7615	Intermediate Similarity	NPD6033	Approved
0.7603	Intermediate Similarity	NPD4634	Approved
0.7583	Intermediate Similarity	NPD6686	Approved
0.7583	Intermediate Similarity	NPD6881	Approved
0.7583	Intermediate Similarity	NPD6899	Approved
0.7563	Intermediate Similarity	NPD5739	Approved
0.7563	Intermediate Similarity	NPD6402	Approved
0.7563	Intermediate Similarity	NPD6675	Approved
0.7563	Intermediate Similarity	NPD7128	Approved
0.7561	Intermediate Similarity	NPD4632	Approved
0.7559	Intermediate Similarity	NPD7503	Approved
0.7541	Intermediate Similarity	NPD6649	Approved
0.7541	Intermediate Similarity	NPD6650	Approved
0.7521	Intermediate Similarity	NPD6372	Approved
0.7521	Intermediate Similarity	NPD6373	Approved
0.752	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5697	Approved
0.7459	Intermediate Similarity	NPD6883	Approved
0.7459	Intermediate Similarity	NPD7102	Approved
0.7459	Intermediate Similarity	NPD7290	Approved
0.7438	Intermediate Similarity	NPD7320	Approved
0.7414	Intermediate Similarity	NPD6083	Phase 2
0.7414	Intermediate Similarity	NPD6084	Phase 2
0.7398	Intermediate Similarity	NPD8130	Phase 1
0.7398	Intermediate Similarity	NPD6847	Approved
0.7398	Intermediate Similarity	NPD6869	Approved
0.7398	Intermediate Similarity	NPD6617	Approved
0.7391	Intermediate Similarity	NPD5695	Phase 3
0.7377	Intermediate Similarity	NPD6012	Approved
0.7377	Intermediate Similarity	NPD6014	Approved
0.7377	Intermediate Similarity	NPD6013	Approved
0.7368	Intermediate Similarity	NPD5956	Approved
0.7355	Intermediate Similarity	NPD5701	Approved
0.735	Intermediate Similarity	NPD5696	Approved
0.7308	Intermediate Similarity	NPD7604	Phase 2
0.7295	Intermediate Similarity	NPD6011	Approved
0.7288	Intermediate Similarity	NPD5285	Approved
0.7288	Intermediate Similarity	NPD5286	Approved
0.7288	Intermediate Similarity	NPD4696	Approved
0.7287	Intermediate Similarity	NPD5983	Phase 2
0.7265	Intermediate Similarity	NPD4755	Approved
0.7241	Intermediate Similarity	NPD4629	Approved
0.7241	Intermediate Similarity	NPD5210	Approved
0.7236	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6336	Discontinued
0.7188	Intermediate Similarity	NPD7327	Approved
0.7188	Intermediate Similarity	NPD7328	Approved
0.7167	Intermediate Similarity	NPD4633	Approved
0.7167	Intermediate Similarity	NPD5225	Approved
0.7167	Intermediate Similarity	NPD5211	Phase 2
0.7167	Intermediate Similarity	NPD5224	Approved
0.7167	Intermediate Similarity	NPD5226	Approved
0.7143	Intermediate Similarity	NPD4700	Approved
0.7132	Intermediate Similarity	NPD7516	Approved
0.712	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5174	Approved
0.7107	Intermediate Similarity	NPD5175	Approved
0.7105	Intermediate Similarity	NPD4753	Phase 2
0.709	Intermediate Similarity	NPD8337	Approved
0.709	Intermediate Similarity	NPD8336	Approved
0.7083	Intermediate Similarity	NPD5223	Approved
0.7077	Intermediate Similarity	NPD8294	Approved
0.7077	Intermediate Similarity	NPD8377	Approved
0.7049	Intermediate Similarity	NPD5141	Approved
0.7049	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6067	Discontinued
0.7031	Intermediate Similarity	NPD6274	Approved
0.7023	Intermediate Similarity	NPD8380	Approved
0.7023	Intermediate Similarity	NPD8335	Approved
0.7023	Intermediate Similarity	NPD8378	Approved
0.7023	Intermediate Similarity	NPD8033	Approved
0.7023	Intermediate Similarity	NPD8379	Approved
0.7023	Intermediate Similarity	NPD8296	Approved
0.7016	Intermediate Similarity	NPD4730	Approved
0.7016	Intermediate Similarity	NPD4729	Approved
0.7008	Intermediate Similarity	NPD8133	Approved
0.7	Intermediate Similarity	NPD7100	Approved
0.7	Intermediate Similarity	NPD7101	Approved
0.6992	Remote Similarity	NPD4768	Approved
0.6992	Remote Similarity	NPD4767	Approved
0.6934	Remote Similarity	NPD7260	Phase 2
0.6929	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD6335	Approved
0.6905	Remote Similarity	NPD5247	Approved
0.6905	Remote Similarity	NPD5250	Approved
0.6905	Remote Similarity	NPD5248	Approved
0.6905	Remote Similarity	NPD5251	Approved
0.6905	Remote Similarity	NPD5249	Phase 3
0.6891	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5222	Approved
0.6891	Remote Similarity	NPD5221	Approved
0.688	Remote Similarity	NPD5128	Approved
0.687	Remote Similarity	NPD6672	Approved
0.687	Remote Similarity	NPD4522	Approved
0.687	Remote Similarity	NPD5737	Approved
0.6846	Remote Similarity	NPD6317	Approved
0.6846	Remote Similarity	NPD7115	Discovery
0.6842	Remote Similarity	NPD5279	Phase 3
0.6842	Remote Similarity	NPD5690	Phase 2
0.6838	Remote Similarity	NPD6050	Approved
0.6838	Remote Similarity	NPD6079	Approved
0.6833	Remote Similarity	NPD5173	Approved
0.6829	Remote Similarity	NPD4754	Approved
0.6814	Remote Similarity	NPD3665	Phase 1
0.6814	Remote Similarity	NPD3666	Approved
0.6814	Remote Similarity	NPD3133	Approved
0.681	Remote Similarity	NPD6904	Approved
0.681	Remote Similarity	NPD6080	Approved
0.681	Remote Similarity	NPD5328	Approved
0.681	Remote Similarity	NPD6673	Approved
0.6794	Remote Similarity	NPD6313	Approved
0.6794	Remote Similarity	NPD6314	Approved
0.6767	Remote Similarity	NPD6909	Approved
0.6767	Remote Similarity	NPD6908	Approved
0.6754	Remote Similarity	NPD5329	Approved
0.6752	Remote Similarity	NPD5692	Phase 3
0.675	Remote Similarity	NPD4697	Phase 3
0.6724	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5282	Discontinued
0.672	Remote Similarity	NPD6008	Approved
0.6719	Remote Similarity	NPD5215	Approved
0.6719	Remote Similarity	NPD5216	Approved
0.6719	Remote Similarity	NPD5217	Approved
0.6716	Remote Similarity	NPD8080	Discontinued
0.6696	Remote Similarity	NPD6409	Approved
0.6696	Remote Similarity	NPD7334	Approved
0.6696	Remote Similarity	NPD5280	Approved
0.6696	Remote Similarity	NPD6684	Approved
0.6696	Remote Similarity	NPD7521	Approved
0.6696	Remote Similarity	NPD7146	Approved
0.6696	Remote Similarity	NPD5330	Approved
0.6696	Remote Similarity	NPD4694	Approved
0.6695	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6643	Remote Similarity	NPD6845	Suspended
0.6643	Remote Similarity	NPD8338	Approved
0.6642	Remote Similarity	NPD8513	Phase 3
0.6642	Remote Similarity	NPD8515	Approved
0.6642	Remote Similarity	NPD8516	Approved
0.6642	Remote Similarity	NPD8517	Approved
0.6641	Remote Similarity	NPD5169	Approved
0.6641	Remote Similarity	NPD5135	Approved
0.6641	Remote Similarity	NPD6868	Approved
0.6641	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6399	Phase 3
0.6639	Remote Similarity	NPD4202	Approved
0.6614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5127	Approved
0.6581	Remote Similarity	NPD6903	Approved
0.6555	Remote Similarity	NPD5284	Approved
0.6555	Remote Similarity	NPD5693	Phase 1
0.6555	Remote Similarity	NPD5281	Approved
0.6555	Remote Similarity	NPD6411	Approved
0.6552	Remote Similarity	NPD6098	Approved
0.6535	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6333	Approved
0.6528	Remote Similarity	NPD6334	Approved
0.6522	Remote Similarity	NPD4786	Approved
0.6519	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6371	Approved
0.6504	Remote Similarity	NPD7638	Approved
0.65	Remote Similarity	NPD6914	Discontinued
0.6491	Remote Similarity	NPD4221	Approved
0.6491	Remote Similarity	NPD4223	Phase 3
0.6452	Remote Similarity	NPD7639	Approved
0.6452	Remote Similarity	NPD7640	Approved
0.6439	Remote Similarity	NPD5167	Approved
0.6435	Remote Similarity	NPD4788	Approved
0.641	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.641	Remote Similarity	NPD3618	Phase 1
0.6406	Remote Similarity	NPD6614	Approved
0.6402	Remote Similarity	NPD7799	Discontinued
0.6393	Remote Similarity	NPD5654	Approved
0.6387	Remote Similarity	NPD6101	Approved
0.6387	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD5168	Approved
0.6349	Remote Similarity	NPD5091	Approved
0.6348	Remote Similarity	NPD3667	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