NPASS Compound

Structure

NPC472770 OpenBabel07101718182D 44 48 0 0 1 0 0 0 0 0999 V2000 0.9176 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7864 0.8612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1348 -3.4791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1348 -2.0101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6348 -1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1349 -0.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6158 -0.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0543 -4.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1245 0.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0543 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6348 -0.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4623 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0824 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9204 1.3612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3258 -2.8913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3155 0.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0543 -0.1388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0543 -1.4792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1883 -2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9335 0.0511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2054 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6702 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3644 0.3601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4739 -0.4739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6213 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6245 -0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6348 -1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4739 -1.1441 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6213 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6702 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9204 2.3612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4122 -3.2981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6777 -2.4792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8846 0.3601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9975 2.6254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3827 -2.5419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0367 -1.7090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1883 -3.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0543 0.8612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4303 -1.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1565 1.3383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6245 -0.9000 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 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 8 39 1 0 0 0 0 9 16 2 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 11 28 1 0 0 0 0 12 21 1 0 0 0 0 13 31 1 0 0 0 0 14 32 2 0 0 0 0 14 40 1 0 0 0 0 15 33 2 0 0 0 0 15 41 1 0 0 0 0 16 24 1 0 0 0 0 16 27 1 0 0 0 0 17 25 1 0 0 0 0 17 40 1 1 0 0 0 18 28 1 0 0 0 0 18 29 1 6 0 0 0 19 34 2 0 0 0 0 19 39 1 0 0 0 0 20 35 1 6 0 0 0 20 43 1 0 0 0 0 21 36 2 0 0 0 0 21 42 1 0 0 0 0 22 13 1 6 0 0 0 22 23 1 0 0 0 0 22 26 1 0 0 0 0 23 29 1 0 0 0 0 23 37 2 0 0 0 0 24 30 1 6 0 0 0 24 42 1 0 0 0 0 25 29 1 1 0 0 0 25 44 1 0 0 0 0 26 30 1 6 0 0 0 26 41 1 0 0 0 0 27 38 2 0 0 0 0 27 43 1 0 0 0 0 29 6 1 6 0 0 0 30 31 1 6 0 0 0 31 12 1 6 0 0 0 31 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.23
Volume:	595.131
LogP:	2.978
LogD:	1.757
LogS:	-4.729
# Rotatable Bonds:	8
TPSA:	185.1
# H-Bond Aceptor:	13
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	6.794
Fsp3:	0.645
Lipinski Rule-of-5:	Rejected
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:	-5.498
MDCK Permeability:	9.03E-05
Pgp-inhibitor:	0.196
Pgp-substrate:	0.93
Human Intestinal Absorption (HIA):	0.91
20% Bioavailability (F20%):	0.825
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.323
Plasma Protein Binding (PPB):	61.39%
Volume Distribution (VD):	0.722
Pgp-substrate:	28.45%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.057
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.067
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.178
CYP3A4-substrate:	0.53

ADMET: Excretion

Clearance (CL):	4.634
Half-life (T1/2):	0.812

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.551
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.74
Rat Oral Acute Toxicity:	0.865
Maximum Recommended Daily Dose:	0.76
Skin Sensitization:	0.525
Carcinogencity:	0.443
Eye Corrosion:	0.004
Eye Irritation:	0.024
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC472770

Natural Product ID:	NPC472770
*Common Name:**	QEONDWGUVMACPI-PWLCZKCNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QEONDWGUVMACPI-PWLCZKCNSA-N
Standard InCHI:	InChI=1S/C31H38O13/c1-13-22-23(37)29(6)18(10-19(34)39-8)28(4,5)11-17(40-14(2)32)25(29)44-31(13)12-21(36)42-24(16-9-20(35)43-27(16)38)30(31,7)26(22)41-15(3)33/h9,17-18,20,22,24-26,35H,1,10-12H2,2-8H3/t17-,18-,20-,22-,24-,25-,26-,29-,30+,31-/m0/s1
SMILES:	COC(=O)C[C@H]1C(C)(C)C[C@@H]([C@H]2[C@]1(C)C(=O)[C@@H]1C(=C)[C@]3(O2)[C@]([C@H]1OC(=O)C)(C)[C@@H](OC(=O)C3)C1=C[C@H](OC1=O)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582099
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic 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
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17655260]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[19296669]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	Longlin County of Guangxi Province, China	2012-JUL	PMID[25970729]
NPO4584	Cipadessa cinerascens	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
EC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	100000.0	nM	PMID[516721]

☑ 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 NPC472770 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	289
0.1-0.2	1672
0.2-0.3	4728
0.3-0.4	7780
0.4-0.5	12670
0.5-0.6	7685
0.6-0.7	5918
0.7-0.8	1887
0.8-0.85	64
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9833	High Similarity	NPC472769
0.9412	High Similarity	NPC472768
0.888	High Similarity	NPC175186
0.881	High Similarity	NPC471170
0.873	High Similarity	NPC104382
0.8651	High Similarity	NPC311534
0.8583	High Similarity	NPC470851
0.8516	High Similarity	NPC476855
0.8462	Intermediate Similarity	NPC471234
0.8438	Intermediate Similarity	NPC476854
0.8425	Intermediate Similarity	NPC471357
0.8425	Intermediate Similarity	NPC117702
0.8425	Intermediate Similarity	NPC146456
0.8425	Intermediate Similarity	NPC287423
0.8425	Intermediate Similarity	NPC469757
0.84	Intermediate Similarity	NPC470419
0.8385	Intermediate Similarity	NPC104585
0.8385	Intermediate Similarity	NPC298783
0.8385	Intermediate Similarity	NPC157817
0.8385	Intermediate Similarity	NPC225385
0.8372	Intermediate Similarity	NPC476852
0.8372	Intermediate Similarity	NPC173347
0.8359	Intermediate Similarity	NPC476859
0.8359	Intermediate Similarity	NPC473620
0.8359	Intermediate Similarity	NPC470850
0.8333	Intermediate Similarity	NPC27363
0.8333	Intermediate Similarity	NPC469382
0.832	Intermediate Similarity	NPC472001
0.8308	Intermediate Similarity	NPC471855
0.8295	Intermediate Similarity	NPC469752
0.8295	Intermediate Similarity	NPC86159
0.8295	Intermediate Similarity	NPC471358
0.8295	Intermediate Similarity	NPC231529
0.8295	Intermediate Similarity	NPC471361
0.8295	Intermediate Similarity	NPC10823
0.8295	Intermediate Similarity	NPC70542
0.8295	Intermediate Similarity	NPC89514
0.8295	Intermediate Similarity	NPC476851
0.8295	Intermediate Similarity	NPC9499
0.8295	Intermediate Similarity	NPC6108
0.8295	Intermediate Similarity	NPC471360
0.8295	Intermediate Similarity	NPC469751
0.8295	Intermediate Similarity	NPC251866
0.8295	Intermediate Similarity	NPC469755
0.8295	Intermediate Similarity	NPC469754
0.8295	Intermediate Similarity	NPC219085
0.8295	Intermediate Similarity	NPC469753
0.8295	Intermediate Similarity	NPC17896
0.8295	Intermediate Similarity	NPC197707
0.8295	Intermediate Similarity	NPC471352
0.8295	Intermediate Similarity	NPC284406
0.8295	Intermediate Similarity	NPC180079
0.8295	Intermediate Similarity	NPC471359
0.8281	Intermediate Similarity	NPC42399
0.8268	Intermediate Similarity	NPC469379
0.8268	Intermediate Similarity	NPC86346
0.8268	Intermediate Similarity	NPC75856
0.8254	Intermediate Similarity	NPC269642
0.8244	Intermediate Similarity	NPC142756
0.8244	Intermediate Similarity	NPC88668
0.824	Intermediate Similarity	NPC472004
0.8231	Intermediate Similarity	NPC16569
0.8231	Intermediate Similarity	NPC159338
0.8231	Intermediate Similarity	NPC476863
0.8231	Intermediate Similarity	NPC476862
0.8231	Intermediate Similarity	NPC253456
0.8226	Intermediate Similarity	NPC470420
0.8211	Intermediate Similarity	NPC106228
0.8211	Intermediate Similarity	NPC138372
0.8203	Intermediate Similarity	NPC250556
0.8203	Intermediate Similarity	NPC469750
0.8175	Intermediate Similarity	NPC471999
0.8175	Intermediate Similarity	NPC470418
0.8175	Intermediate Similarity	NPC470829
0.8175	Intermediate Similarity	NPC472000
0.8175	Intermediate Similarity	NPC473228
0.8175	Intermediate Similarity	NPC310511
0.8168	Intermediate Similarity	NPC42670
0.8168	Intermediate Similarity	NPC19124
0.8168	Intermediate Similarity	NPC93416
0.8162	Intermediate Similarity	NPC48414
0.8162	Intermediate Similarity	NPC5153
0.816	Intermediate Similarity	NPC19028
0.816	Intermediate Similarity	NPC9674
0.8154	Intermediate Similarity	NPC476966
0.8154	Intermediate Similarity	NPC471407
0.8154	Intermediate Similarity	NPC91
0.814	Intermediate Similarity	NPC179412
0.814	Intermediate Similarity	NPC471356
0.814	Intermediate Similarity	NPC240070
0.814	Intermediate Similarity	NPC329784
0.814	Intermediate Similarity	NPC470882
0.814	Intermediate Similarity	NPC298841
0.813	Intermediate Similarity	NPC178289
0.812	Intermediate Similarity	NPC171619
0.811	Intermediate Similarity	NPC28532
0.811	Intermediate Similarity	NPC107493
0.8106	Intermediate Similarity	NPC476221
0.8106	Intermediate Similarity	NPC247190
0.8106	Intermediate Similarity	NPC469749
0.8106	Intermediate Similarity	NPC32793
0.8106	Intermediate Similarity	NPC146857
0.8106	Intermediate Similarity	NPC477709
0.8106	Intermediate Similarity	NPC116075
0.8095	Intermediate Similarity	NPC151616
0.8095	Intermediate Similarity	NPC48692
0.808	Intermediate Similarity	NPC475372
0.8077	Intermediate Similarity	NPC245094
0.8077	Intermediate Similarity	NPC270109
0.8062	Intermediate Similarity	NPC222307
0.8062	Intermediate Similarity	NPC47113
0.8062	Intermediate Similarity	NPC174367
0.806	Intermediate Similarity	NPC59288
0.8047	Intermediate Similarity	NPC471392
0.8047	Intermediate Similarity	NPC472399
0.8047	Intermediate Similarity	NPC129992
0.8045	Intermediate Similarity	NPC478072
0.8045	Intermediate Similarity	NPC329636
0.8043	Intermediate Similarity	NPC471172
0.8031	Intermediate Similarity	NPC202051
0.8031	Intermediate Similarity	NPC46570
0.803	Intermediate Similarity	NPC231240
0.8016	Intermediate Similarity	NPC475041
0.8016	Intermediate Similarity	NPC472667
0.8016	Intermediate Similarity	NPC312536
0.8016	Intermediate Similarity	NPC469380
0.8015	Intermediate Similarity	NPC140092
0.8015	Intermediate Similarity	NPC232785
0.8015	Intermediate Similarity	NPC188234
0.8015	Intermediate Similarity	NPC125077
0.8015	Intermediate Similarity	NPC473593
0.8015	Intermediate Similarity	NPC329986
0.8015	Intermediate Similarity	NPC276838
0.8	Intermediate Similarity	NPC473265
0.8	Intermediate Similarity	NPC473656
0.8	Intermediate Similarity	NPC470171
0.7986	Intermediate Similarity	NPC48813
0.7986	Intermediate Similarity	NPC194854
0.7985	Intermediate Similarity	NPC194716
0.7984	Intermediate Similarity	NPC470922
0.7984	Intermediate Similarity	NPC318135
0.7971	Intermediate Similarity	NPC471171
0.797	Intermediate Similarity	NPC316915
0.7955	Intermediate Similarity	NPC473838
0.7955	Intermediate Similarity	NPC475389
0.7953	Intermediate Similarity	NPC281840
0.7953	Intermediate Similarity	NPC4548
0.7953	Intermediate Similarity	NPC470312
0.7953	Intermediate Similarity	NPC143755
0.7953	Intermediate Similarity	NPC109973
0.7941	Intermediate Similarity	NPC75616
0.7941	Intermediate Similarity	NPC79250
0.7941	Intermediate Similarity	NPC290746
0.7937	Intermediate Similarity	NPC13710
0.7937	Intermediate Similarity	NPC234522
0.7929	Intermediate Similarity	NPC16729
0.7929	Intermediate Similarity	NPC475462
0.7926	Intermediate Similarity	NPC329675
0.7923	Intermediate Similarity	NPC293112
0.792	Intermediate Similarity	NPC49492
0.792	Intermediate Similarity	NPC266728
0.792	Intermediate Similarity	NPC470793
0.792	Intermediate Similarity	NPC471816
0.7917	Intermediate Similarity	NPC470975
0.7917	Intermediate Similarity	NPC103088
0.7917	Intermediate Similarity	NPC470979
0.7907	Intermediate Similarity	NPC469789
0.7907	Intermediate Similarity	NPC204812
0.7907	Intermediate Similarity	NPC473979
0.7903	Intermediate Similarity	NPC962
0.7903	Intermediate Similarity	NPC264153
0.7903	Intermediate Similarity	NPC250109
0.7895	Intermediate Similarity	NPC180902
0.7895	Intermediate Similarity	NPC475139
0.7891	Intermediate Similarity	NPC472401
0.7879	Intermediate Similarity	NPC13071
0.7879	Intermediate Similarity	NPC470880
0.7874	Intermediate Similarity	NPC304260
0.7874	Intermediate Similarity	NPC472933
0.7874	Intermediate Similarity	NPC5883
0.7874	Intermediate Similarity	NPC5292
0.7874	Intermediate Similarity	NPC473270
0.7874	Intermediate Similarity	NPC29639
0.7874	Intermediate Similarity	NPC44899
0.7869	Intermediate Similarity	NPC273433
0.7863	Intermediate Similarity	NPC473253
0.7863	Intermediate Similarity	NPC305496
0.7857	Intermediate Similarity	NPC203862
0.7857	Intermediate Similarity	NPC152615
0.7857	Intermediate Similarity	NPC474483
0.7857	Intermediate Similarity	NPC218970
0.7857	Intermediate Similarity	NPC473968
0.7846	Intermediate Similarity	NPC172154
0.7846	Intermediate Similarity	NPC81736
0.7846	Intermediate Similarity	NPC8369
0.7846	Intermediate Similarity	NPC473255
0.7846	Intermediate Similarity	NPC32868
0.7846	Intermediate Similarity	NPC241456
0.784	Intermediate Similarity	NPC90472
0.784	Intermediate Similarity	NPC326542

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 NPC472770 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	1927
0.2-0.3	3823
0.3-0.4	2075
0.4-0.5	598
0.5-0.6	266
0.6-0.7	156
0.7-0.8	55
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
0.8295	Intermediate Similarity	NPD7319	Approved
0.8203	Intermediate Similarity	NPD7507	Approved
0.7752	Intermediate Similarity	NPD8033	Approved
0.7734	Intermediate Similarity	NPD7516	Approved
0.7692	Intermediate Similarity	NPD6370	Approved
0.7669	Intermediate Similarity	NPD7736	Approved
0.7656	Intermediate Similarity	NPD7328	Approved
0.7656	Intermediate Similarity	NPD7327	Approved
0.7642	Intermediate Similarity	NPD6686	Approved
0.7594	Intermediate Similarity	NPD8293	Discontinued
0.7576	Intermediate Similarity	NPD7492	Approved
0.7538	Intermediate Similarity	NPD8377	Approved
0.7538	Intermediate Similarity	NPD8294	Approved
0.7538	Intermediate Similarity	NPD6054	Approved
0.7519	Intermediate Similarity	NPD6616	Approved
0.7481	Intermediate Similarity	NPD8380	Approved
0.7481	Intermediate Similarity	NPD8379	Approved
0.7481	Intermediate Similarity	NPD8296	Approved
0.7481	Intermediate Similarity	NPD8378	Approved
0.7481	Intermediate Similarity	NPD8335	Approved
0.7463	Intermediate Similarity	NPD7078	Approved
0.7442	Intermediate Similarity	NPD7115	Discovery
0.7405	Intermediate Similarity	NPD6059	Approved
0.7405	Intermediate Similarity	NPD6319	Approved
0.7402	Intermediate Similarity	NPD6053	Discontinued
0.7381	Intermediate Similarity	NPD6371	Approved
0.7348	Intermediate Similarity	NPD6015	Approved
0.7348	Intermediate Similarity	NPD6016	Approved
0.7293	Intermediate Similarity	NPD5988	Approved
0.7266	Intermediate Similarity	NPD6882	Approved
0.7266	Intermediate Similarity	NPD8297	Approved
0.7218	Intermediate Similarity	NPD7503	Approved
0.72	Intermediate Similarity	NPD6008	Approved
0.7188	Intermediate Similarity	NPD6649	Approved
0.7188	Intermediate Similarity	NPD6650	Approved
0.7176	Intermediate Similarity	NPD6009	Approved
0.7165	Intermediate Similarity	NPD6373	Approved
0.7165	Intermediate Similarity	NPD6372	Approved
0.7143	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7131	Intermediate Similarity	NPD4225	Approved
0.7111	Intermediate Similarity	NPD8328	Phase 3
0.709	Intermediate Similarity	NPD8515	Approved
0.709	Intermediate Similarity	NPD8517	Approved
0.709	Intermediate Similarity	NPD8513	Phase 3
0.709	Intermediate Similarity	NPD8516	Approved
0.7087	Intermediate Similarity	NPD7320	Approved
0.7087	Intermediate Similarity	NPD6899	Approved
0.7087	Intermediate Similarity	NPD6881	Approved
0.7077	Intermediate Similarity	NPD4632	Approved
0.7073	Intermediate Similarity	NPD7639	Approved
0.7073	Intermediate Similarity	NPD7640	Approved
0.7063	Intermediate Similarity	NPD7128	Approved
0.7063	Intermediate Similarity	NPD6675	Approved
0.7063	Intermediate Similarity	NPD6402	Approved
0.7063	Intermediate Similarity	NPD5739	Approved
0.7008	Intermediate Similarity	NPD5697	Approved
0.6992	Remote Similarity	NPD7638	Approved
0.6977	Remote Similarity	NPD7102	Approved
0.6977	Remote Similarity	NPD6883	Approved
0.6977	Remote Similarity	NPD7290	Approved
0.6953	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8133	Approved
0.6923	Remote Similarity	NPD6869	Approved
0.6923	Remote Similarity	NPD6617	Approved
0.6923	Remote Similarity	NPD6847	Approved
0.6923	Remote Similarity	NPD8130	Phase 1
0.6906	Remote Similarity	NPD6033	Approved
0.6899	Remote Similarity	NPD6012	Approved
0.6899	Remote Similarity	NPD6014	Approved
0.6899	Remote Similarity	NPD6013	Approved
0.6875	Remote Similarity	NPD5701	Approved
0.6861	Remote Similarity	NPD7604	Phase 2
0.6846	Remote Similarity	NPD4634	Approved
0.6846	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5983	Phase 2
0.6833	Remote Similarity	NPD5785	Approved
0.6831	Remote Similarity	NPD8338	Approved
0.6825	Remote Similarity	NPD5211	Phase 2
0.6822	Remote Similarity	NPD6011	Approved
0.6791	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6336	Discontinued
0.6761	Remote Similarity	NPD7260	Phase 2
0.6748	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD8336	Approved
0.6667	Remote Similarity	NPD8337	Approved
0.664	Remote Similarity	NPD4755	Approved
0.6619	Remote Similarity	NPD6067	Discontinued
0.6614	Remote Similarity	NPD5344	Discontinued
0.6597	Remote Similarity	NPD6845	Suspended
0.6596	Remote Similarity	NPD8074	Phase 3
0.6593	Remote Similarity	NPD6274	Approved
0.6587	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5696	Approved
0.6569	Remote Similarity	NPD7101	Approved
0.6569	Remote Similarity	NPD7100	Approved
0.6562	Remote Similarity	NPD7632	Discontinued
0.6562	Remote Similarity	NPD5224	Approved
0.6562	Remote Similarity	NPD4633	Approved
0.6562	Remote Similarity	NPD5225	Approved
0.6562	Remote Similarity	NPD5226	Approved
0.6557	Remote Similarity	NPD46	Approved
0.6557	Remote Similarity	NPD6698	Approved
0.6535	Remote Similarity	NPD6648	Approved
0.6535	Remote Similarity	NPD4700	Approved
0.6512	Remote Similarity	NPD5175	Approved
0.6512	Remote Similarity	NPD5174	Approved
0.6508	Remote Similarity	NPD6083	Phase 2
0.6508	Remote Similarity	NPD6084	Phase 2
0.6496	Remote Similarity	NPD6335	Approved
0.6484	Remote Similarity	NPD5223	Approved
0.648	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6921	Approved
0.6467	Remote Similarity	NPD7799	Discontinued
0.6452	Remote Similarity	NPD5778	Approved
0.6452	Remote Similarity	NPD5779	Approved
0.6452	Remote Similarity	NPD6399	Phase 3
0.6439	Remote Similarity	NPD4729	Approved
0.6439	Remote Similarity	NPD4730	Approved
0.6423	Remote Similarity	NPD6317	Approved
0.6418	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5363	Approved
0.6412	Remote Similarity	NPD4767	Approved
0.6412	Remote Similarity	NPD4768	Approved
0.6383	Remote Similarity	NPD7642	Approved
0.6377	Remote Similarity	NPD6313	Approved
0.6377	Remote Similarity	NPD6314	Approved
0.6371	Remote Similarity	NPD7983	Approved
0.6371	Remote Similarity	NPD7637	Suspended
0.6371	Remote Similarity	NPD6079	Approved
0.6364	Remote Similarity	NPD5786	Approved
0.6364	Remote Similarity	NPD7625	Phase 1
0.6357	Remote Similarity	NPD6909	Approved
0.6357	Remote Similarity	NPD6908	Approved
0.6349	Remote Similarity	NPD4629	Approved
0.6349	Remote Similarity	NPD5695	Phase 3
0.6349	Remote Similarity	NPD5210	Approved
0.6345	Remote Similarity	NPD5956	Approved
0.6343	Remote Similarity	NPD5249	Phase 3
0.6343	Remote Similarity	NPD5248	Approved
0.6343	Remote Similarity	NPD5247	Approved
0.6343	Remote Similarity	NPD5251	Approved
0.6343	Remote Similarity	NPD5250	Approved
0.6341	Remote Similarity	NPD1695	Approved
0.6341	Remote Similarity	NPD5328	Approved
0.6336	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.632	Remote Similarity	NPD4202	Approved
0.6316	Remote Similarity	NPD5128	Approved
0.6309	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5282	Discontinued
0.6268	Remote Similarity	NPD7830	Approved
0.6268	Remote Similarity	NPD7829	Approved
0.6267	Remote Similarity	NPD6334	Approved
0.6267	Remote Similarity	NPD6333	Approved
0.626	Remote Similarity	NPD4754	Approved
0.626	Remote Similarity	NPD6903	Approved
0.6241	Remote Similarity	NPD8444	Approved
0.624	Remote Similarity	NPD5693	Phase 1
0.624	Remote Similarity	NPD6411	Approved
0.6231	Remote Similarity	NPD1700	Approved
0.623	Remote Similarity	NPD6409	Approved
0.623	Remote Similarity	NPD5330	Approved
0.623	Remote Similarity	NPD7521	Approved
0.623	Remote Similarity	NPD6684	Approved
0.623	Remote Similarity	NPD7334	Approved
0.623	Remote Similarity	NPD7146	Approved
0.6198	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD8451	Approved
0.6179	Remote Similarity	NPD4250	Approved
0.6179	Remote Similarity	NPD4251	Approved
0.6176	Remote Similarity	NPD5215	Approved
0.6176	Remote Similarity	NPD5217	Approved
0.6176	Remote Similarity	NPD5216	Approved
0.6172	Remote Similarity	NPD5221	Approved
0.6172	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD5222	Approved
0.6172	Remote Similarity	NPD4697	Phase 3
0.6172	Remote Similarity	NPD7839	Suspended
0.6167	Remote Similarity	NPD4270	Approved
0.6167	Remote Similarity	NPD6435	Approved
0.6167	Remote Similarity	NPD4269	Approved
0.6148	Remote Similarity	NPD1694	Approved
0.6142	Remote Similarity	NPD6001	Approved
0.6138	Remote Similarity	NPD8448	Approved
0.6129	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD5173	Approved
0.6124	Remote Similarity	NPD7902	Approved
0.6116	Remote Similarity	NPD5362	Discontinued
0.6115	Remote Similarity	NPD6868	Approved
0.6111	Remote Similarity	NPD5281	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