NPASS Compound

Structure

NPC75856 OpenBabel07101718302D 44 49 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 6.7628 -3.2843 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 5.1682 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 5.7764 -3.1205 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 9 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 8 39 1 0 0 0 0 9 16 2 0 0 0 0 10 11 1 0 0 0 0 10 19 2 0 0 0 0 11 40 1 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 13 25 1 0 0 0 0 14 23 1 0 0 0 0 14 24 1 0 0 0 0 15 32 1 0 0 0 0 15 41 1 0 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 17 26 2 0 0 0 0 18 35 2 0 0 0 0 18 42 1 0 0 0 0 19 31 1 0 0 0 0 20 19 1 1 0 0 0 21 12 1 1 0 0 0 21 26 1 0 0 0 0 21 43 1 0 0 0 0 22 33 1 1 0 0 0 22 34 1 0 0 0 0 23 33 1 6 0 0 0 23 36 1 0 0 0 0 24 32 1 6 0 0 0 24 42 1 0 0 0 0 25 39 1 6 0 0 0 25 43 1 0 0 0 0 26 34 1 0 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 27 41 1 6 0 0 0 28 32 1 1 0 0 0 28 33 1 0 0 0 0 29 34 1 6 0 0 0 29 44 1 0 0 0 0 30 37 2 0 0 0 0 30 44 1 0 0 0 0 31 38 2 0 0 0 0 31 40 1 0 0 0 0 32 5 1 1 0 0 0 33 6 1 1 0 0 0 34 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	614.31
Volume:	617.365
LogP:	3.147
LogD:	2.882
LogS:	-4.411
# Rotatable Bonds:	7
TPSA:	133.89
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	5.866
Fsp3:	0.706
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:	-5.172
MDCK Permeability:	6.206430407473817e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.644

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.19
Plasma Protein Binding (PPB):	93.0049057006836%
Volume Distribution (VD):	2.75
Pgp-substrate:	7.046126365661621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.167
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.485
CYP2C9-inhibitor:	0.68
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.824
CYP3A4-substrate:	0.757

ADMET: Excretion

Clearance (CL):	5.553
Half-life (T1/2):	0.604

ADMET: Toxicity

hERG Blockers:	0.759
Human Hepatotoxicity (H-HT):	0.906
Drug-inuced Liver Injury (DILI):	0.718
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.627
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.228
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC75856

Natural Product ID:	NPC75856
*Common Name:**	Chisonimbolinin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IELVEPMRFQCOKL-DBGUIWQXSA-N
Standard InCHI:	InChI=1S/C34H46O10/c1-9-16(2)30(37)44-29-27-28-32(5,15-41-27)24(42-18(4)35)14-23(36)33(28,6)22-13-25(39-8)43-21-12-20(19-10-11-40-31(19)38)17(3)26(21)34(22,29)7/h9-10,20-25,27-29,36H,11-15H2,1-8H3/b16-9+/t20-,21+,22-,23+,24-,25-,27-,28+,29-,32-,33+,34-/m1/s1
SMILES:	CO[C@@H]1O[C@H]2C[C@H](C(=C2[C@]2([C@H](C1)[C@@]1(C)[C@@H](O)C[C@H]([C@@]3([C@@H]1[C@H]([C@H]2OC(=O)/C(=C/C)/C)OC3)C)OC(=O)C)C)C)C1=CCOC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077082
PubChem CID:	44607453
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[570505]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[570505]

☑ 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 NPC75856 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	254
0.1-0.2	1492
0.2-0.3	4397
0.3-0.4	7404
0.4-0.5	12892
0.5-0.6	7665
0.6-0.7	6033
0.7-0.8	2417
0.8-0.85	129
0.85-0.9	7
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC86346
1.0	High Similarity	NPC469379
0.9912	High Similarity	NPC469382
0.9649	High Similarity	NPC151616
0.9561	High Similarity	NPC469380
0.9211	High Similarity	NPC90472
0.8803	High Similarity	NPC471816
0.8699	High Similarity	NPC298841
0.856	High Similarity	NPC470851
0.8548	High Similarity	NPC42399
0.8512	High Similarity	NPC470312
0.8487	Intermediate Similarity	NPC106228
0.8487	Intermediate Similarity	NPC138372
0.848	Intermediate Similarity	NPC470850
0.8475	Intermediate Similarity	NPC470120
0.8455	Intermediate Similarity	NPC27363
0.8443	Intermediate Similarity	NPC204731
0.843	Intermediate Similarity	NPC9674
0.843	Intermediate Similarity	NPC19028
0.8425	Intermediate Similarity	NPC472769
0.8417	Intermediate Similarity	NPC473968
0.84	Intermediate Similarity	NPC179412
0.84	Intermediate Similarity	NPC471357
0.84	Intermediate Similarity	NPC471356
0.84	Intermediate Similarity	NPC469757
0.84	Intermediate Similarity	NPC146456
0.84	Intermediate Similarity	NPC329784
0.84	Intermediate Similarity	NPC240070
0.84	Intermediate Similarity	NPC117702
0.8361	Intermediate Similarity	NPC241192
0.8359	Intermediate Similarity	NPC88668
0.8346	Intermediate Similarity	NPC471170
0.8333	Intermediate Similarity	NPC311534
0.832	Intermediate Similarity	NPC250556
0.832	Intermediate Similarity	NPC469750
0.8319	Intermediate Similarity	NPC157441
0.8291	Intermediate Similarity	NPC206618
0.8281	Intermediate Similarity	NPC93416
0.8281	Intermediate Similarity	NPC471855
0.8279	Intermediate Similarity	NPC476529
0.8279	Intermediate Similarity	NPC475775
0.8279	Intermediate Similarity	NPC161065
0.8279	Intermediate Similarity	NPC122971
0.8268	Intermediate Similarity	NPC140092
0.8268	Intermediate Similarity	NPC9499
0.8268	Intermediate Similarity	NPC469751
0.8268	Intermediate Similarity	NPC86159
0.8268	Intermediate Similarity	NPC6108
0.8268	Intermediate Similarity	NPC188234
0.8268	Intermediate Similarity	NPC219085
0.8268	Intermediate Similarity	NPC232785
0.8268	Intermediate Similarity	NPC180079
0.8268	Intermediate Similarity	NPC469755
0.8268	Intermediate Similarity	NPC17896
0.8268	Intermediate Similarity	NPC472770
0.8268	Intermediate Similarity	NPC276838
0.8268	Intermediate Similarity	NPC469752
0.8268	Intermediate Similarity	NPC175186
0.8268	Intermediate Similarity	NPC469754
0.8268	Intermediate Similarity	NPC329986
0.8268	Intermediate Similarity	NPC469753
0.8268	Intermediate Similarity	NPC471352
0.8268	Intermediate Similarity	NPC89514
0.8268	Intermediate Similarity	NPC471358
0.8268	Intermediate Similarity	NPC284406
0.8268	Intermediate Similarity	NPC10823
0.8268	Intermediate Similarity	NPC471360
0.8268	Intermediate Similarity	NPC125077
0.8268	Intermediate Similarity	NPC471361
0.8268	Intermediate Similarity	NPC251866
0.8268	Intermediate Similarity	NPC70542
0.8268	Intermediate Similarity	NPC104382
0.8268	Intermediate Similarity	NPC471359
0.8268	Intermediate Similarity	NPC197707
0.8264	Intermediate Similarity	NPC284068
0.8264	Intermediate Similarity	NPC13713
0.8264	Intermediate Similarity	NPC474483
0.825	Intermediate Similarity	NPC472274
0.8235	Intermediate Similarity	NPC194951
0.8235	Intermediate Similarity	NPC470063
0.8235	Intermediate Similarity	NPC12046
0.8217	Intermediate Similarity	NPC225385
0.8217	Intermediate Similarity	NPC469749
0.8217	Intermediate Similarity	NPC104585
0.8217	Intermediate Similarity	NPC32793
0.8217	Intermediate Similarity	NPC477709
0.8217	Intermediate Similarity	NPC142756
0.8217	Intermediate Similarity	NPC157817
0.8217	Intermediate Similarity	NPC476221
0.8217	Intermediate Similarity	NPC298783
0.8217	Intermediate Similarity	NPC116075
0.8217	Intermediate Similarity	NPC247190
0.8217	Intermediate Similarity	NPC146857
0.8211	Intermediate Similarity	NPC476150
0.8211	Intermediate Similarity	NPC107338
0.8211	Intermediate Similarity	NPC476127
0.8211	Intermediate Similarity	NPC109607
0.8205	Intermediate Similarity	NPC177524
0.8205	Intermediate Similarity	NPC219900
0.8205	Intermediate Similarity	NPC38948
0.8205	Intermediate Similarity	NPC392
0.8203	Intermediate Similarity	NPC16569
0.8203	Intermediate Similarity	NPC159338
0.8203	Intermediate Similarity	NPC253456
0.8197	Intermediate Similarity	NPC473617
0.8197	Intermediate Similarity	NPC473828
0.8189	Intermediate Similarity	NPC270109
0.8174	Intermediate Similarity	NPC120009
0.8154	Intermediate Similarity	NPC329636
0.8151	Intermediate Similarity	NPC17791
0.8145	Intermediate Similarity	NPC476204
0.8145	Intermediate Similarity	NPC170084
0.8145	Intermediate Similarity	NPC202051
0.814	Intermediate Similarity	NPC19124
0.814	Intermediate Similarity	NPC42670
0.8136	Intermediate Similarity	NPC40728
0.8134	Intermediate Similarity	NPC5153
0.8134	Intermediate Similarity	NPC48414
0.813	Intermediate Similarity	NPC477071
0.8125	Intermediate Similarity	NPC91
0.8125	Intermediate Similarity	NPC471407
0.8099	Intermediate Similarity	NPC178289
0.8092	Intermediate Similarity	NPC194716
0.8083	Intermediate Similarity	NPC222834
0.8083	Intermediate Similarity	NPC317460
0.8083	Intermediate Similarity	NPC470025
0.8083	Intermediate Similarity	NPC328074
0.8083	Intermediate Similarity	NPC321272
0.8067	Intermediate Similarity	NPC475134
0.8067	Intermediate Similarity	NPC316708
0.8067	Intermediate Similarity	NPC119550
0.8067	Intermediate Similarity	NPC83005
0.8067	Intermediate Similarity	NPC475563
0.8065	Intermediate Similarity	NPC48692
0.8065	Intermediate Similarity	NPC143755
0.8065	Intermediate Similarity	NPC4548
0.8062	Intermediate Similarity	NPC173347
0.8051	Intermediate Similarity	NPC128795
0.8051	Intermediate Similarity	NPC217921
0.8051	Intermediate Similarity	NPC135015
0.8051	Intermediate Similarity	NPC48548
0.8047	Intermediate Similarity	NPC473620
0.8047	Intermediate Similarity	NPC245094
0.8034	Intermediate Similarity	NPC218158
0.8033	Intermediate Similarity	NPC302471
0.8033	Intermediate Similarity	NPC243981
0.8031	Intermediate Similarity	NPC174367
0.8031	Intermediate Similarity	NPC222307
0.8031	Intermediate Similarity	NPC47113
0.803	Intermediate Similarity	NPC329675
0.803	Intermediate Similarity	NPC59288
0.8017	Intermediate Similarity	NPC75167
0.8017	Intermediate Similarity	NPC264153
0.8017	Intermediate Similarity	NPC311592
0.8017	Intermediate Similarity	NPC470027
0.8016	Intermediate Similarity	NPC472768
0.8016	Intermediate Similarity	NPC471392
0.8016	Intermediate Similarity	NPC473979
0.8016	Intermediate Similarity	NPC41129
0.8016	Intermediate Similarity	NPC469352
0.8015	Intermediate Similarity	NPC471234
0.8015	Intermediate Similarity	NPC471172
0.8	Intermediate Similarity	NPC469656
0.8	Intermediate Similarity	NPC474846
0.8	Intermediate Similarity	NPC471412
0.8	Intermediate Similarity	NPC475668
0.8	Intermediate Similarity	NPC478152
0.8	Intermediate Similarity	NPC473921
0.8	Intermediate Similarity	NPC180902
0.8	Intermediate Similarity	NPC478150
0.8	Intermediate Similarity	NPC475139
0.8	Intermediate Similarity	NPC475480
0.8	Intermediate Similarity	NPC478153
0.8	Intermediate Similarity	NPC470026
0.8	Intermediate Similarity	NPC469655
0.7984	Intermediate Similarity	NPC77689
0.7984	Intermediate Similarity	NPC5883
0.7984	Intermediate Similarity	NPC211093
0.7984	Intermediate Similarity	NPC473636
0.7984	Intermediate Similarity	NPC29639
0.7984	Intermediate Similarity	NPC231529
0.7984	Intermediate Similarity	NPC470914
0.7984	Intermediate Similarity	NPC312536
0.7984	Intermediate Similarity	NPC476966
0.7984	Intermediate Similarity	NPC304260
0.7984	Intermediate Similarity	NPC472667
0.7984	Intermediate Similarity	NPC44899
0.7984	Intermediate Similarity	NPC473839
0.7983	Intermediate Similarity	NPC273433
0.7983	Intermediate Similarity	NPC112457
0.7983	Intermediate Similarity	NPC316974
0.797	Intermediate Similarity	NPC596
0.7969	Intermediate Similarity	NPC470780
0.7967	Intermediate Similarity	NPC475323
0.7967	Intermediate Similarity	NPC471355
0.7967	Intermediate Similarity	NPC34390
0.7967	Intermediate Similarity	NPC158344
0.7967	Intermediate Similarity	NPC473656
0.7967	Intermediate Similarity	NPC471354
0.7967	Intermediate Similarity	NPC152615

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 NPC75856 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	1751
0.2-0.3	3744
0.3-0.4	2288
0.4-0.5	654
0.5-0.6	287
0.6-0.7	166
0.7-0.8	40
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
0.832	Intermediate Similarity	NPD7507	Approved
0.8268	Intermediate Similarity	NPD7319	Approved
0.8205	Intermediate Similarity	NPD6686	Approved
0.7984	Intermediate Similarity	NPD7516	Approved
0.7903	Intermediate Similarity	NPD7328	Approved
0.7903	Intermediate Similarity	NPD7327	Approved
0.7857	Intermediate Similarity	NPD8296	Approved
0.7857	Intermediate Similarity	NPD8379	Approved
0.7857	Intermediate Similarity	NPD8033	Approved
0.7857	Intermediate Similarity	NPD8335	Approved
0.7857	Intermediate Similarity	NPD8380	Approved
0.7857	Intermediate Similarity	NPD8378	Approved
0.7778	Intermediate Similarity	NPD8377	Approved
0.7778	Intermediate Similarity	NPD8294	Approved
0.7769	Intermediate Similarity	NPD7736	Approved
0.7692	Intermediate Similarity	NPD8293	Discontinued
0.7656	Intermediate Similarity	NPD6370	Approved
0.7557	Intermediate Similarity	NPD7078	Approved
0.7538	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD6054	Approved
0.7481	Intermediate Similarity	NPD6616	Approved
0.7398	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6412	Phase 2
0.7373	Intermediate Similarity	NPD7638	Approved
0.7364	Intermediate Similarity	NPD6059	Approved
0.736	Intermediate Similarity	NPD6882	Approved
0.736	Intermediate Similarity	NPD8297	Approved
0.7339	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD8328	Phase 3
0.7311	Intermediate Similarity	NPD7639	Approved
0.7311	Intermediate Similarity	NPD7640	Approved
0.7308	Intermediate Similarity	NPD6016	Approved
0.7308	Intermediate Similarity	NPD6015	Approved
0.7308	Intermediate Similarity	NPD7503	Approved
0.7266	Intermediate Similarity	NPD6009	Approved
0.7258	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD5988	Approved
0.7236	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD4225	Approved
0.7222	Intermediate Similarity	NPD6053	Discontinued
0.7176	Intermediate Similarity	NPD8515	Approved
0.7176	Intermediate Similarity	NPD8513	Phase 3
0.7176	Intermediate Similarity	NPD8516	Approved
0.7176	Intermediate Similarity	NPD8517	Approved
0.7165	Intermediate Similarity	NPD8133	Approved
0.7132	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6319	Approved
0.7097	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6067	Discontinued
0.704	Intermediate Similarity	NPD6899	Approved
0.704	Intermediate Similarity	NPD7320	Approved
0.704	Intermediate Similarity	NPD6881	Approved
0.7031	Intermediate Similarity	NPD4632	Approved
0.7016	Intermediate Similarity	NPD7128	Approved
0.7016	Intermediate Similarity	NPD5739	Approved
0.7016	Intermediate Similarity	NPD6402	Approved
0.7016	Intermediate Similarity	NPD6008	Approved
0.7016	Intermediate Similarity	NPD6675	Approved
0.7008	Intermediate Similarity	NPD6650	Approved
0.7008	Intermediate Similarity	NPD6649	Approved
0.7008	Intermediate Similarity	NPD8130	Phase 1
0.7	Intermediate Similarity	NPD7115	Discovery
0.6984	Remote Similarity	NPD6372	Approved
0.6984	Remote Similarity	NPD6373	Approved
0.696	Remote Similarity	NPD5697	Approved
0.6929	Remote Similarity	NPD7102	Approved
0.6929	Remote Similarity	NPD6883	Approved
0.6929	Remote Similarity	NPD7290	Approved
0.6905	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6869	Approved
0.6875	Remote Similarity	NPD6617	Approved
0.6875	Remote Similarity	NPD6847	Approved
0.6861	Remote Similarity	NPD6033	Approved
0.685	Remote Similarity	NPD6014	Approved
0.685	Remote Similarity	NPD6012	Approved
0.685	Remote Similarity	NPD6013	Approved
0.6833	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5344	Discontinued
0.6825	Remote Similarity	NPD5701	Approved
0.6815	Remote Similarity	NPD7604	Phase 2
0.6797	Remote Similarity	NPD6371	Approved
0.6791	Remote Similarity	NPD5983	Phase 2
0.678	Remote Similarity	NPD6698	Approved
0.678	Remote Similarity	NPD46	Approved
0.6774	Remote Similarity	NPD7632	Discontinued
0.6772	Remote Similarity	NPD6011	Approved
0.6715	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8074	Phase 3
0.664	Remote Similarity	NPD5211	Phase 2
0.6615	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5285	Approved
0.6613	Remote Similarity	NPD4696	Approved
0.6613	Remote Similarity	NPD6648	Approved
0.6613	Remote Similarity	NPD5286	Approved
0.6612	Remote Similarity	NPD7748	Approved
0.6585	Remote Similarity	NPD7902	Approved
0.6585	Remote Similarity	NPD4755	Approved
0.6583	Remote Similarity	NPD6079	Approved
0.6555	Remote Similarity	NPD5328	Approved
0.6541	Remote Similarity	NPD6274	Approved
0.6538	Remote Similarity	NPD4634	Approved
0.6535	Remote Similarity	NPD5141	Approved
0.6533	Remote Similarity	NPD7625	Phase 1
0.6529	Remote Similarity	NPD6399	Phase 3
0.6524	Remote Similarity	NPD7799	Discontinued
0.6519	Remote Similarity	NPD7100	Approved
0.6519	Remote Similarity	NPD7101	Approved
0.6508	Remote Similarity	NPD5224	Approved
0.6508	Remote Similarity	NPD5225	Approved
0.6508	Remote Similarity	NPD4633	Approved
0.6508	Remote Similarity	NPD5226	Approved
0.65	Remote Similarity	NPD7838	Discovery
0.648	Remote Similarity	NPD4700	Approved
0.6479	Remote Similarity	NPD7260	Phase 2
0.6457	Remote Similarity	NPD5174	Approved
0.6457	Remote Similarity	NPD5175	Approved
0.6452	Remote Similarity	NPD6084	Phase 2
0.6452	Remote Similarity	NPD6083	Phase 2
0.6449	Remote Similarity	NPD7829	Approved
0.6449	Remote Similarity	NPD7830	Approved
0.6446	Remote Similarity	NPD7515	Phase 2
0.6446	Remote Similarity	NPD7983	Approved
0.6444	Remote Similarity	NPD6335	Approved
0.6434	Remote Similarity	NPD8338	Approved
0.6434	Remote Similarity	NPD6845	Suspended
0.6429	Remote Similarity	NPD5223	Approved
0.6423	Remote Similarity	NPD6921	Approved
0.6423	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5779	Approved
0.6393	Remote Similarity	NPD5778	Approved
0.6385	Remote Similarity	NPD4730	Approved
0.6385	Remote Similarity	NPD4729	Approved
0.6371	Remote Similarity	NPD5222	Approved
0.6371	Remote Similarity	NPD5221	Approved
0.6371	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6317	Approved
0.6357	Remote Similarity	NPD4768	Approved
0.6357	Remote Similarity	NPD4767	Approved
0.6356	Remote Similarity	NPD1694	Approved
0.6341	Remote Similarity	NPD7900	Approved
0.6341	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6903	Approved
0.6324	Remote Similarity	NPD6314	Approved
0.6324	Remote Similarity	NPD6313	Approved
0.632	Remote Similarity	NPD5173	Approved
0.6311	Remote Similarity	NPD8034	Phase 2
0.6311	Remote Similarity	NPD7637	Suspended
0.6311	Remote Similarity	NPD8035	Phase 2
0.6304	Remote Similarity	NPD6909	Approved
0.6304	Remote Similarity	NPD6908	Approved
0.6303	Remote Similarity	NPD3618	Phase 1
0.6303	Remote Similarity	NPD7521	Approved
0.6303	Remote Similarity	NPD7334	Approved
0.6303	Remote Similarity	NPD7146	Approved
0.6303	Remote Similarity	NPD6684	Approved
0.6303	Remote Similarity	NPD5330	Approved
0.6303	Remote Similarity	NPD6409	Approved
0.6296	Remote Similarity	NPD6868	Approved
0.6294	Remote Similarity	NPD5956	Approved
0.629	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD5249	Phase 3
0.6288	Remote Similarity	NPD5248	Approved
0.6288	Remote Similarity	NPD5247	Approved
0.6288	Remote Similarity	NPD5251	Approved
0.6288	Remote Similarity	NPD5250	Approved
0.6281	Remote Similarity	NPD1695	Approved
0.6268	Remote Similarity	NPD8337	Approved
0.6268	Remote Similarity	NPD8336	Approved
0.626	Remote Similarity	NPD4202	Approved
0.626	Remote Similarity	NPD5128	Approved
0.6259	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.624	Remote Similarity	NPD4697	Phase 3
0.623	Remote Similarity	NPD5785	Approved
0.6202	Remote Similarity	NPD4754	Approved
0.6198	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6411	Approved
0.616	Remote Similarity	NPD5695	Phase 3
0.6142	Remote Similarity	NPD5696	Approved
0.6134	Remote Similarity	NPD3133	Approved
0.6134	Remote Similarity	NPD3666	Approved
0.6134	Remote Similarity	NPD4786	Approved
0.6134	Remote Similarity	NPD3665	Phase 1
0.6127	Remote Similarity	NPD8451	Approved
0.6119	Remote Similarity	NPD5217	Approved
0.6119	Remote Similarity	NPD5216	Approved
0.6119	Remote Similarity	NPD5215	Approved
0.6116	Remote Similarity	NPD4250	Approved
0.6116	Remote Similarity	NPD7524	Approved
0.6116	Remote Similarity	NPD4251	Approved
0.6116	Remote Similarity	NPD3573	Approved
0.6111	Remote Similarity	NPD7839	Suspended
0.6107	Remote Similarity	NPD6334	Approved
0.6107	Remote Similarity	NPD6333	Approved
0.6102	Remote Similarity	NPD3667	Approved
0.6099	Remote Similarity	NPD7122	Discontinued

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