NPASS Compound

Structure

NPC469382 OpenBabel07101719512D 43 48 0 0 1 0 0 0 0 0999 V2000 1.7045 3.0938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4513 4.0678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3781 1.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8898 1.5206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5286 2.0989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0357 -0.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5437 -0.8650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5630 2.5809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8781 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1160 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2787 0.3638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2302 2.5938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4364 3.0679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3781 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9954 1.0733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5691 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8781 -1.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9818 -0.4705 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6506 -0.1526 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2665 1.1769 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4250 -2.1843 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1871 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0117 1.5292 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8702 1.0163 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1383 1.0422 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2948 2.5550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6232 1.6743 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8552 0.0164 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1234 0.0424 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9356 0.0751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8877 -1.1241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7764 -3.1205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1682 3.0420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.5878 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 6.2342 2.5042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1609 1.6242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4290 -2.0946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2799 1.5551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 8 15 2 0 0 0 0 9 10 1 0 0 0 0 9 18 2 0 0 0 0 10 39 1 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 12 24 1 0 0 0 0 13 22 1 0 0 0 0 13 23 1 0 0 0 0 14 31 1 0 0 0 0 14 40 1 0 0 0 0 15 29 1 0 0 0 0 16 19 1 0 0 0 0 16 25 2 0 0 0 0 17 34 2 0 0 0 0 17 41 1 0 0 0 0 18 30 1 0 0 0 0 19 18 1 1 0 0 0 20 11 1 1 0 0 0 20 25 1 0 0 0 0 20 42 1 0 0 0 0 21 32 1 1 0 0 0 21 33 1 0 0 0 0 22 32 1 6 0 0 0 22 35 1 0 0 0 0 23 31 1 6 0 0 0 23 41 1 0 0 0 0 24 36 1 6 0 0 0 24 42 1 0 0 0 0 25 33 1 0 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 26 40 1 6 0 0 0 27 31 1 1 0 0 0 27 32 1 0 0 0 0 28 33 1 6 0 0 0 28 43 1 0 0 0 0 29 37 2 0 0 0 0 29 43 1 0 0 0 0 30 38 2 0 0 0 0 30 39 1 0 0 0 0 31 5 1 1 0 0 0 32 6 1 1 0 0 0 33 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	842.32
Volume:	789.11
LogP:	0.01
LogD:	-0.223
LogS:	-2.985
# Rotatable Bonds:	16
TPSA:	305.6
# H-Bond Aceptor:	20
# H-Bond Donor:	11
# Rings:	6
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.077
Synthetic Accessibility Score:	5.756
Fsp3:	0.641
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.472
MDCK Permeability:	4.5992328523425385e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	59.16360092163086%
Volume Distribution (VD):	-0.124
Pgp-substrate:	11.283208847045898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	0.582
Half-life (T1/2):	0.732

ADMET: Toxicity

hERG Blockers:	0.504
Human Hepatotoxicity (H-HT):	0.026
Drug-inuced Liver Injury (DILI):	0.864
AMES Toxicity:	0.209
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.948
Carcinogencity:	0.139
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC469382

Natural Product ID:	NPC469382
*Common Name:**	Chisonimbolinin D
IUPAC Name:	n.a.
Synonyms:	Chisonimbolinin D
Standard InCHIKey:	OVOJZOGJIHRBMM-GKMUKERHSA-N
Standard InCHI:	InChI=1S/C33H44O10/c1-8-15(2)29(37)43-28-26-27-31(5,14-40-26)23(41-17(4)34)13-22(35)32(27,6)21-12-24(36)42-20-11-19(18-9-10-39-30(18)38)16(3)25(20)33(21,28)7/h8-9,19-24,26-28,35-36H,10-14H2,1-7H3/b15-8+/t19-,20+,21-,22+,23-,24-,26-,27+,28-,31-,32+,33-/m1/s1
SMILES:	C/C=C(/C(=O)O[C@@H]1[C@@H]2OC[C@]3([C@H]2[C@]([C@@H]2[C@]1(C)C1=C(C)[C@@H](C[C@@H]1O[C@H](C2)O)C1=CCOC1=O)(C)[C@H](C[C@H]3OC(=O)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077084
PubChem CID:	44604737
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids 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
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943621]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Yunnan, China	2007-May	PMID[21288727]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32208696]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	50000.0	nM	PMID[468159]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	32000.0	nM	PMID[468159]

☑ 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 NPC469382 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	253
0.1-0.2	1467
0.2-0.3	4308
0.3-0.4	7373
0.4-0.5	13060
0.5-0.6	7500
0.6-0.7	6238
0.7-0.8	2371
0.8-0.85	115
0.85-0.9	5
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC469379
0.9912	High Similarity	NPC86346
0.9912	High Similarity	NPC75856
0.9646	High Similarity	NPC469380
0.9561	High Similarity	NPC151616
0.9292	High Similarity	NPC90472
0.8718	High Similarity	NPC471816
0.8629	High Similarity	NPC470851
0.8618	High Similarity	NPC298841
0.8559	High Similarity	NPC138372
0.8559	High Similarity	NPC106228
0.8548	High Similarity	NPC470850
0.8547	High Similarity	NPC470120
0.85	High Similarity	NPC9674
0.85	High Similarity	NPC19028
0.8492	Intermediate Similarity	NPC472769
0.8487	Intermediate Similarity	NPC473968
0.8468	Intermediate Similarity	NPC42399
0.843	Intermediate Similarity	NPC470312
0.8413	Intermediate Similarity	NPC471170
0.8374	Intermediate Similarity	NPC27363
0.8361	Intermediate Similarity	NPC204731
0.8347	Intermediate Similarity	NPC475775
0.8347	Intermediate Similarity	NPC476529
0.8333	Intermediate Similarity	NPC104382
0.8333	Intermediate Similarity	NPC284068
0.8333	Intermediate Similarity	NPC13713
0.8333	Intermediate Similarity	NPC472770
0.8333	Intermediate Similarity	NPC175186
0.832	Intermediate Similarity	NPC179412
0.832	Intermediate Similarity	NPC329784
0.832	Intermediate Similarity	NPC146456
0.832	Intermediate Similarity	NPC471356
0.832	Intermediate Similarity	NPC240070
0.832	Intermediate Similarity	NPC469757
0.832	Intermediate Similarity	NPC471357
0.832	Intermediate Similarity	NPC117702
0.8305	Intermediate Similarity	NPC12046
0.8305	Intermediate Similarity	NPC470063
0.8305	Intermediate Similarity	NPC194951
0.8281	Intermediate Similarity	NPC88668
0.8279	Intermediate Similarity	NPC241192
0.8279	Intermediate Similarity	NPC107338
0.8279	Intermediate Similarity	NPC109607
0.8276	Intermediate Similarity	NPC38948
0.8254	Intermediate Similarity	NPC311534
0.824	Intermediate Similarity	NPC469750
0.824	Intermediate Similarity	NPC250556
0.8235	Intermediate Similarity	NPC157441
0.8205	Intermediate Similarity	NPC206618
0.8203	Intermediate Similarity	NPC471855
0.8203	Intermediate Similarity	NPC93416
0.8197	Intermediate Similarity	NPC161065
0.8197	Intermediate Similarity	NPC122971
0.8189	Intermediate Similarity	NPC469754
0.8189	Intermediate Similarity	NPC469751
0.8189	Intermediate Similarity	NPC284406
0.8189	Intermediate Similarity	NPC469753
0.8189	Intermediate Similarity	NPC471358
0.8189	Intermediate Similarity	NPC276838
0.8189	Intermediate Similarity	NPC180079
0.8189	Intermediate Similarity	NPC89514
0.8189	Intermediate Similarity	NPC471361
0.8189	Intermediate Similarity	NPC10823
0.8189	Intermediate Similarity	NPC329986
0.8189	Intermediate Similarity	NPC471360
0.8189	Intermediate Similarity	NPC70542
0.8189	Intermediate Similarity	NPC86159
0.8189	Intermediate Similarity	NPC197707
0.8189	Intermediate Similarity	NPC140092
0.8189	Intermediate Similarity	NPC125077
0.8189	Intermediate Similarity	NPC471359
0.8189	Intermediate Similarity	NPC219085
0.8189	Intermediate Similarity	NPC469752
0.8189	Intermediate Similarity	NPC9499
0.8189	Intermediate Similarity	NPC188234
0.8189	Intermediate Similarity	NPC251866
0.8189	Intermediate Similarity	NPC471352
0.8189	Intermediate Similarity	NPC17896
0.8189	Intermediate Similarity	NPC6108
0.8189	Intermediate Similarity	NPC469755
0.8189	Intermediate Similarity	NPC232785
0.8182	Intermediate Similarity	NPC474483
0.8167	Intermediate Similarity	NPC178289
0.8167	Intermediate Similarity	NPC472274
0.814	Intermediate Similarity	NPC32793
0.814	Intermediate Similarity	NPC298783
0.814	Intermediate Similarity	NPC157817
0.814	Intermediate Similarity	NPC225385
0.814	Intermediate Similarity	NPC477709
0.814	Intermediate Similarity	NPC104585
0.814	Intermediate Similarity	NPC116075
0.814	Intermediate Similarity	NPC247190
0.814	Intermediate Similarity	NPC469749
0.814	Intermediate Similarity	NPC476221
0.814	Intermediate Similarity	NPC142756
0.814	Intermediate Similarity	NPC146857
0.8136	Intermediate Similarity	NPC475563
0.8136	Intermediate Similarity	NPC475134
0.813	Intermediate Similarity	NPC143755
0.813	Intermediate Similarity	NPC476127
0.813	Intermediate Similarity	NPC4548
0.813	Intermediate Similarity	NPC476150
0.8125	Intermediate Similarity	NPC253456
0.8125	Intermediate Similarity	NPC16569
0.8125	Intermediate Similarity	NPC159338
0.812	Intermediate Similarity	NPC219900
0.812	Intermediate Similarity	NPC177524
0.812	Intermediate Similarity	NPC392
0.8115	Intermediate Similarity	NPC473617
0.8115	Intermediate Similarity	NPC473828
0.811	Intermediate Similarity	NPC473620
0.811	Intermediate Similarity	NPC270109
0.8087	Intermediate Similarity	NPC120009
0.808	Intermediate Similarity	NPC472768
0.808	Intermediate Similarity	NPC473979
0.808	Intermediate Similarity	NPC469352
0.8077	Intermediate Similarity	NPC329636
0.8077	Intermediate Similarity	NPC471234
0.807	Intermediate Similarity	NPC471412
0.8067	Intermediate Similarity	NPC474846
0.8067	Intermediate Similarity	NPC469656
0.8067	Intermediate Similarity	NPC473921
0.8067	Intermediate Similarity	NPC17791
0.8067	Intermediate Similarity	NPC475480
0.8067	Intermediate Similarity	NPC475668
0.8067	Intermediate Similarity	NPC469655
0.8065	Intermediate Similarity	NPC170084
0.8065	Intermediate Similarity	NPC202051
0.8065	Intermediate Similarity	NPC476204
0.8062	Intermediate Similarity	NPC19124
0.8062	Intermediate Similarity	NPC42670
0.806	Intermediate Similarity	NPC48414
0.806	Intermediate Similarity	NPC5153
0.8051	Intermediate Similarity	NPC40728
0.8051	Intermediate Similarity	NPC273433
0.8049	Intermediate Similarity	NPC77689
0.8049	Intermediate Similarity	NPC312536
0.8049	Intermediate Similarity	NPC473839
0.8049	Intermediate Similarity	NPC477071
0.8049	Intermediate Similarity	NPC472667
0.8049	Intermediate Similarity	NPC211093
0.8049	Intermediate Similarity	NPC473636
0.8047	Intermediate Similarity	NPC91
0.8047	Intermediate Similarity	NPC471407
0.8047	Intermediate Similarity	NPC231529
0.8034	Intermediate Similarity	NPC67321
0.8034	Intermediate Similarity	NPC187435
0.8033	Intermediate Similarity	NPC475323
0.8033	Intermediate Similarity	NPC473656
0.8033	Intermediate Similarity	NPC10721
0.8017	Intermediate Similarity	NPC123117
0.8016	Intermediate Similarity	NPC470922
0.8015	Intermediate Similarity	NPC194716
0.8	Intermediate Similarity	NPC317460
0.8	Intermediate Similarity	NPC476081
0.8	Intermediate Similarity	NPC321272
0.8	Intermediate Similarity	NPC474516
0.8	Intermediate Similarity	NPC222834
0.8	Intermediate Similarity	NPC162973
0.8	Intermediate Similarity	NPC470025
0.8	Intermediate Similarity	NPC152117
0.8	Intermediate Similarity	NPC328074
0.8	Intermediate Similarity	NPC234042
0.7984	Intermediate Similarity	NPC173347
0.7984	Intermediate Similarity	NPC476852
0.7984	Intermediate Similarity	NPC476855
0.7984	Intermediate Similarity	NPC48692
0.7984	Intermediate Similarity	NPC472004
0.7983	Intermediate Similarity	NPC316708
0.7983	Intermediate Similarity	NPC119550
0.7983	Intermediate Similarity	NPC83005
0.7982	Intermediate Similarity	NPC471413
0.7982	Intermediate Similarity	NPC47024
0.7969	Intermediate Similarity	NPC245094
0.7967	Intermediate Similarity	NPC475372
0.7967	Intermediate Similarity	NPC124676
0.7967	Intermediate Similarity	NPC146280
0.7966	Intermediate Similarity	NPC275539
0.7966	Intermediate Similarity	NPC128795
0.7966	Intermediate Similarity	NPC189075
0.7966	Intermediate Similarity	NPC217921
0.7966	Intermediate Similarity	NPC135015
0.7966	Intermediate Similarity	NPC48548
0.7955	Intermediate Similarity	NPC329675
0.7955	Intermediate Similarity	NPC59288
0.7953	Intermediate Similarity	NPC222307
0.7953	Intermediate Similarity	NPC47113
0.7953	Intermediate Similarity	NPC174367
0.7951	Intermediate Similarity	NPC471127
0.7951	Intermediate Similarity	NPC243981
0.7951	Intermediate Similarity	NPC154363
0.7951	Intermediate Similarity	NPC302471
0.7951	Intermediate Similarity	NPC234858
0.7949	Intermediate Similarity	NPC218158
0.7941	Intermediate Similarity	NPC471172
0.7937	Intermediate Similarity	NPC471392
0.7937	Intermediate Similarity	NPC41129
0.7937	Intermediate Similarity	NPC129992
0.7934	Intermediate Similarity	NPC264153

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 NPC469382 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	1714
0.2-0.3	3733
0.3-0.4	2318
0.4-0.5	677
0.5-0.6	284
0.6-0.7	170
0.7-0.8	38
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.824	Intermediate Similarity	NPD7507	Approved
0.8189	Intermediate Similarity	NPD7319	Approved
0.812	Intermediate Similarity	NPD6686	Approved
0.7903	Intermediate Similarity	NPD7516	Approved
0.7823	Intermediate Similarity	NPD7327	Approved
0.7823	Intermediate Similarity	NPD7328	Approved
0.7778	Intermediate Similarity	NPD8033	Approved
0.7778	Intermediate Similarity	NPD8296	Approved
0.7778	Intermediate Similarity	NPD8380	Approved
0.7778	Intermediate Similarity	NPD8335	Approved
0.7778	Intermediate Similarity	NPD8379	Approved
0.7778	Intermediate Similarity	NPD8378	Approved
0.7698	Intermediate Similarity	NPD8377	Approved
0.7698	Intermediate Similarity	NPD8294	Approved
0.7692	Intermediate Similarity	NPD7736	Approved
0.7615	Intermediate Similarity	NPD8293	Discontinued
0.7578	Intermediate Similarity	NPD6370	Approved
0.7481	Intermediate Similarity	NPD7078	Approved
0.7462	Intermediate Similarity	NPD7492	Approved
0.7459	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7638	Approved
0.7422	Intermediate Similarity	NPD6054	Approved
0.7419	Intermediate Similarity	NPD8297	Approved
0.7405	Intermediate Similarity	NPD6616	Approved
0.7398	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD7639	Approved
0.7373	Intermediate Similarity	NPD7640	Approved
0.7295	Intermediate Similarity	NPD6412	Phase 2
0.7295	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4225	Approved
0.7287	Intermediate Similarity	NPD6059	Approved
0.728	Intermediate Similarity	NPD6053	Discontinued
0.728	Intermediate Similarity	NPD6882	Approved
0.7252	Intermediate Similarity	NPD8328	Phase 3
0.7231	Intermediate Similarity	NPD7503	Approved
0.7231	Intermediate Similarity	NPD6016	Approved
0.7231	Intermediate Similarity	NPD6015	Approved
0.7188	Intermediate Similarity	NPD6009	Approved
0.7177	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5988	Approved
0.7154	Intermediate Similarity	NPD6319	Approved
0.7154	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD8513	Phase 3
0.7099	Intermediate Similarity	NPD8517	Approved
0.7099	Intermediate Similarity	NPD8515	Approved
0.7099	Intermediate Similarity	NPD8516	Approved
0.7097	Intermediate Similarity	NPD7320	Approved
0.7097	Intermediate Similarity	NPD6881	Approved
0.7097	Intermediate Similarity	NPD6899	Approved
0.7087	Intermediate Similarity	NPD4632	Approved
0.7087	Intermediate Similarity	NPD8133	Approved
0.7073	Intermediate Similarity	NPD6008	Approved
0.7073	Intermediate Similarity	NPD7128	Approved
0.7073	Intermediate Similarity	NPD6675	Approved
0.7073	Intermediate Similarity	NPD5739	Approved
0.7073	Intermediate Similarity	NPD6402	Approved
0.7063	Intermediate Similarity	NPD6650	Approved
0.7063	Intermediate Similarity	NPD6649	Approved
0.7063	Intermediate Similarity	NPD8130	Phase 1
0.7054	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7115	Discovery
0.704	Intermediate Similarity	NPD6373	Approved
0.704	Intermediate Similarity	NPD6372	Approved
0.7016	Intermediate Similarity	NPD5697	Approved
0.6992	Remote Similarity	NPD6067	Discontinued
0.6984	Remote Similarity	NPD6883	Approved
0.6984	Remote Similarity	NPD7102	Approved
0.6984	Remote Similarity	NPD7290	Approved
0.696	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6617	Approved
0.6929	Remote Similarity	NPD6847	Approved
0.6929	Remote Similarity	NPD6869	Approved
0.6905	Remote Similarity	NPD6012	Approved
0.6905	Remote Similarity	NPD6013	Approved
0.6905	Remote Similarity	NPD6014	Approved
0.6891	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5344	Discontinued
0.688	Remote Similarity	NPD5701	Approved
0.6866	Remote Similarity	NPD7604	Phase 2
0.685	Remote Similarity	NPD6371	Approved
0.6842	Remote Similarity	NPD5983	Phase 2
0.6838	Remote Similarity	NPD46	Approved
0.6838	Remote Similarity	NPD6698	Approved
0.6829	Remote Similarity	NPD7632	Discontinued
0.6825	Remote Similarity	NPD6011	Approved
0.6788	Remote Similarity	NPD6033	Approved
0.6765	Remote Similarity	NPD6336	Discontinued
0.6726	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6639	Remote Similarity	NPD7902	Approved
0.6639	Remote Similarity	NPD6079	Approved
0.6639	Remote Similarity	NPD4755	Approved
0.661	Remote Similarity	NPD5328	Approved
0.6594	Remote Similarity	NPD8074	Phase 3
0.6591	Remote Similarity	NPD6274	Approved
0.6589	Remote Similarity	NPD4634	Approved
0.6587	Remote Similarity	NPD5141	Approved
0.6587	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6399	Phase 3
0.6567	Remote Similarity	NPD7101	Approved
0.6567	Remote Similarity	NPD7100	Approved
0.656	Remote Similarity	NPD4633	Approved
0.656	Remote Similarity	NPD5224	Approved
0.656	Remote Similarity	NPD5225	Approved
0.656	Remote Similarity	NPD5226	Approved
0.6555	Remote Similarity	NPD7838	Discovery
0.6538	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD4700	Approved
0.6525	Remote Similarity	NPD7260	Phase 2
0.6508	Remote Similarity	NPD5174	Approved
0.6508	Remote Similarity	NPD5175	Approved
0.6504	Remote Similarity	NPD6083	Phase 2
0.6504	Remote Similarity	NPD6084	Phase 2
0.65	Remote Similarity	NPD7515	Phase 2
0.65	Remote Similarity	NPD7983	Approved
0.6493	Remote Similarity	NPD6335	Approved
0.648	Remote Similarity	NPD5223	Approved
0.6479	Remote Similarity	NPD6845	Suspended
0.6471	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6921	Approved
0.6467	Remote Similarity	NPD7625	Phase 1
0.6466	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7799	Discontinued
0.6446	Remote Similarity	NPD5778	Approved
0.6446	Remote Similarity	NPD5779	Approved
0.6434	Remote Similarity	NPD4729	Approved
0.6434	Remote Similarity	NPD4730	Approved
0.6423	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5222	Approved
0.6423	Remote Similarity	NPD5221	Approved
0.6418	Remote Similarity	NPD6317	Approved
0.641	Remote Similarity	NPD1694	Approved
0.6406	Remote Similarity	NPD4768	Approved
0.6406	Remote Similarity	NPD4767	Approved
0.6393	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7900	Approved
0.6387	Remote Similarity	NPD6903	Approved
0.6377	Remote Similarity	NPD7830	Approved
0.6377	Remote Similarity	NPD7829	Approved
0.6371	Remote Similarity	NPD5173	Approved
0.637	Remote Similarity	NPD6313	Approved
0.637	Remote Similarity	NPD6314	Approved
0.6364	Remote Similarity	NPD7637	Suspended
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD8338	Approved
0.6356	Remote Similarity	NPD7334	Approved
0.6356	Remote Similarity	NPD3618	Phase 1
0.6356	Remote Similarity	NPD6409	Approved
0.6356	Remote Similarity	NPD5330	Approved
0.6356	Remote Similarity	NPD7146	Approved
0.6356	Remote Similarity	NPD6684	Approved
0.6356	Remote Similarity	NPD7521	Approved
0.635	Remote Similarity	NPD6909	Approved
0.635	Remote Similarity	NPD6908	Approved
0.6343	Remote Similarity	NPD6868	Approved
0.6341	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD5249	Phase 3
0.6336	Remote Similarity	NPD5250	Approved
0.6336	Remote Similarity	NPD5247	Approved
0.6336	Remote Similarity	NPD5248	Approved
0.6336	Remote Similarity	NPD5251	Approved
0.6333	Remote Similarity	NPD1695	Approved
0.6311	Remote Similarity	NPD4202	Approved
0.6308	Remote Similarity	NPD5128	Approved
0.629	Remote Similarity	NPD4697	Phase 3
0.6281	Remote Similarity	NPD5785	Approved
0.625	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4754	Approved
0.623	Remote Similarity	NPD6411	Approved
0.6224	Remote Similarity	NPD5956	Approved
0.621	Remote Similarity	NPD5695	Phase 3
0.6197	Remote Similarity	NPD8336	Approved
0.6197	Remote Similarity	NPD8337	Approved
0.619	Remote Similarity	NPD5696	Approved
0.619	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD3666	Approved
0.6186	Remote Similarity	NPD3133	Approved
0.6186	Remote Similarity	NPD4786	Approved
0.6186	Remote Similarity	NPD3665	Phase 1
0.6167	Remote Similarity	NPD4251	Approved
0.6167	Remote Similarity	NPD4250	Approved
0.6167	Remote Similarity	NPD7524	Approved
0.6167	Remote Similarity	NPD3573	Approved
0.6165	Remote Similarity	NPD5216	Approved
0.6165	Remote Similarity	NPD5215	Approved
0.6165	Remote Similarity	NPD5217	Approved
0.616	Remote Similarity	NPD7839	Suspended
0.6154	Remote Similarity	NPD3667	Approved
0.6149	Remote Similarity	NPD6333	Approved
0.6149	Remote Similarity	NPD6334	Approved
0.6134	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7520	Clinical (unspecified phase)

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