NPASS Compound

Structure

NPC83019 OpenBabel07101719512D 34 37 0 0 1 0 0 0 0 0999 V2000 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 26 1 0 0 0 0 3 31 1 0 0 0 0 4 32 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 26 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 21 1 0 0 0 0 12 26 1 0 0 0 0 13 33 1 0 0 0 0 14 25 1 0 0 0 0 15 21 1 0 0 0 0 15 22 1 1 0 0 0 16 23 1 0 0 0 0 16 27 2 0 0 0 0 17 22 1 0 0 0 0 17 28 1 0 0 0 0 18 23 2 0 0 0 0 18 29 1 0 0 0 0 19 20 2 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 34 1 1 0 0 0 22 24 2 0 0 0 0 23 24 1 0 0 0 0 24 33 1 0 0 0 0 25 30 2 0 0 0 0 25 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	469.17
Volume:	464.321
LogP:	3.316
LogD:	2.364
LogS:	-3.983
# Rotatable Bonds:	6
TPSA:	118.67
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	3.513
Fsp3:	0.36
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.907
MDCK Permeability:	4.3194213503738865e-05
Pgp-inhibitor:	0.22
Pgp-substrate:	0.093
Human Intestinal Absorption (HIA):	0.113
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.076

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.615
Plasma Protein Binding (PPB):	85.06539916992188%
Volume Distribution (VD):	1.604
Pgp-substrate:	18.847023010253906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.304
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.712
CYP2C9-inhibitor:	0.089
CYP2C9-substrate:	0.782
CYP2D6-inhibitor:	0.722
CYP2D6-substrate:	0.839
CYP3A4-inhibitor:	0.156
CYP3A4-substrate:	0.808

ADMET: Excretion

Clearance (CL):	9.023
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.476
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.149
Rat Oral Acute Toxicity:	0.182
Maximum Recommended Daily Dose:	0.317
Skin Sensitization:	0.449
Carcinogencity:	0.264
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.823

Download Data

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

Natural Product: NPC83019

Natural Product ID:	NPC83019
*Common Name:**	Chrotacumine D
IUPAC Name:	[(3S,4R)-4-(5,7-dihydroxy-2-methyl-4-oxochromen-8-yl)-1-methylpiperidin-3-yl] 3,4-dimethoxybenzoate
Synonyms:	Chrotacumine D
Standard InCHIKey:	RIKKYJZEZQRRQP-YCRPNKLZSA-N
Standard InCHI:	InChI=1S/C25H27NO8/c1-13-9-16(27)23-18(29)11-17(28)22(24(23)33-13)15-7-8-26(2)12-21(15)34-25(30)14-5-6-19(31-3)20(10-14)32-4/h5-6,9-11,15,21,28-29H,7-8,12H2,1-4H3/t15-,21+/m0/s1
SMILES:	Cc1cc(=O)c2c(cc(c([C@H]3CCN(C)C[C@H]3OC(=O)c3ccc(c(c3)OC)OC)c2o1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078325
PubChem CID:	44557092
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000195] Piperidines [CHEMONTID:0000303] Phenylpiperidines

*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
NPO654	Dysoxylum acutangulum	Species	Meliaceae	Eukaryota	n.a.	alkaloids	n.a.	PMID[19757855]
NPO654	Dysoxylum acutangulum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO654	Dysoxylum acutangulum	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[521228]

☑ 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 NPC83019 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	296
0.1-0.2	1356
0.2-0.3	4040
0.3-0.4	10137
0.4-0.5	7848
0.5-0.6	5283
0.6-0.7	7484
0.7-0.8	5952
0.8-0.85	292
0.85-0.9	5
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9943	High Similarity	NPC204580
0.927	High Similarity	NPC469437
0.92	High Similarity	NPC309692
0.8864	High Similarity	NPC129578
0.8596	High Similarity	NPC13481
0.8596	High Similarity	NPC207575
0.8556	High Similarity	NPC264938
0.8462	Intermediate Similarity	NPC329816
0.8432	Intermediate Similarity	NPC18306
0.8427	Intermediate Similarity	NPC474150
0.8427	Intermediate Similarity	NPC474162
0.8409	Intermediate Similarity	NPC108456
0.8409	Intermediate Similarity	NPC473272
0.8409	Intermediate Similarity	NPC284820
0.84	Intermediate Similarity	NPC31018
0.84	Intermediate Similarity	NPC255807
0.8389	Intermediate Similarity	NPC120593
0.8371	Intermediate Similarity	NPC26326
0.837	Intermediate Similarity	NPC473562
0.8333	Intermediate Similarity	NPC471788
0.8315	Intermediate Similarity	NPC119209
0.8315	Intermediate Similarity	NPC475784
0.8315	Intermediate Similarity	NPC118256
0.8315	Intermediate Similarity	NPC192686
0.8308	Intermediate Similarity	NPC314946
0.8305	Intermediate Similarity	NPC181960
0.8305	Intermediate Similarity	NPC129684
0.8305	Intermediate Similarity	NPC291508
0.8305	Intermediate Similarity	NPC299520
0.8297	Intermediate Similarity	NPC329992
0.8297	Intermediate Similarity	NPC288813
0.8295	Intermediate Similarity	NPC226025
0.8287	Intermediate Similarity	NPC128293
0.8278	Intermediate Similarity	NPC273959
0.8278	Intermediate Similarity	NPC474350
0.8278	Intermediate Similarity	NPC186686
0.8268	Intermediate Similarity	NPC474038
0.8268	Intermediate Similarity	NPC134783
0.8268	Intermediate Similarity	NPC266314
0.8258	Intermediate Similarity	NPC53545
0.8258	Intermediate Similarity	NPC117418
0.8258	Intermediate Similarity	NPC204879
0.8251	Intermediate Similarity	NPC103307
0.8249	Intermediate Similarity	NPC195796
0.8249	Intermediate Similarity	NPC291878
0.8249	Intermediate Similarity	NPC278778
0.8249	Intermediate Similarity	NPC35038
0.8242	Intermediate Similarity	NPC227683
0.8239	Intermediate Similarity	NPC475895
0.8232	Intermediate Similarity	NPC472277
0.8232	Intermediate Similarity	NPC62261
0.8222	Intermediate Similarity	NPC83922
0.8222	Intermediate Similarity	NPC472448
0.8222	Intermediate Similarity	NPC474033
0.8222	Intermediate Similarity	NPC229632
0.8222	Intermediate Similarity	NPC474034
0.8222	Intermediate Similarity	NPC476247
0.8212	Intermediate Similarity	NPC299436
0.8212	Intermediate Similarity	NPC36217
0.8212	Intermediate Similarity	NPC292415
0.8212	Intermediate Similarity	NPC477164
0.8212	Intermediate Similarity	NPC53889
0.8207	Intermediate Similarity	NPC271848
0.8207	Intermediate Similarity	NPC212038
0.8207	Intermediate Similarity	NPC81332
0.8207	Intermediate Similarity	NPC262580
0.8207	Intermediate Similarity	NPC289396
0.8207	Intermediate Similarity	NPC475825
0.8207	Intermediate Similarity	NPC223375
0.8207	Intermediate Similarity	NPC475669
0.8202	Intermediate Similarity	NPC472598
0.8202	Intermediate Similarity	NPC52889
0.8202	Intermediate Similarity	NPC218313
0.8202	Intermediate Similarity	NPC474681
0.8202	Intermediate Similarity	NPC27337
0.8202	Intermediate Similarity	NPC476981
0.8202	Intermediate Similarity	NPC474055
0.8197	Intermediate Similarity	NPC177480
0.8192	Intermediate Similarity	NPC477503
0.8192	Intermediate Similarity	NPC37392
0.8192	Intermediate Similarity	NPC230149
0.8192	Intermediate Similarity	NPC168247
0.8192	Intermediate Similarity	NPC152951
0.8192	Intermediate Similarity	NPC117992
0.8192	Intermediate Similarity	NPC470327
0.8192	Intermediate Similarity	NPC472909
0.8192	Intermediate Similarity	NPC57674
0.8192	Intermediate Similarity	NPC45849
0.8192	Intermediate Similarity	NPC200761
0.8187	Intermediate Similarity	NPC171985
0.8187	Intermediate Similarity	NPC119589
0.8187	Intermediate Similarity	NPC272502
0.8187	Intermediate Similarity	NPC320741
0.8187	Intermediate Similarity	NPC173292
0.8187	Intermediate Similarity	NPC43319
0.8187	Intermediate Similarity	NPC235610
0.8182	Intermediate Similarity	NPC40033
0.8177	Intermediate Similarity	NPC205265
0.8177	Intermediate Similarity	NPC18100
0.8177	Intermediate Similarity	NPC472281
0.8177	Intermediate Similarity	NPC124038
0.8177	Intermediate Similarity	NPC472625
0.8171	Intermediate Similarity	NPC338131
0.8167	Intermediate Similarity	NPC471211
0.8167	Intermediate Similarity	NPC165549
0.8167	Intermediate Similarity	NPC289771
0.8167	Intermediate Similarity	NPC103201
0.8167	Intermediate Similarity	NPC472632
0.8167	Intermediate Similarity	NPC97812
0.8167	Intermediate Similarity	NPC167678
0.8167	Intermediate Similarity	NPC57715
0.8167	Intermediate Similarity	NPC29876
0.8167	Intermediate Similarity	NPC234644
0.8167	Intermediate Similarity	NPC474186
0.8167	Intermediate Similarity	NPC142252
0.8167	Intermediate Similarity	NPC471499
0.8167	Intermediate Similarity	NPC473106
0.8167	Intermediate Similarity	NPC471212
0.8167	Intermediate Similarity	NPC112418
0.8167	Intermediate Similarity	NPC474187
0.8167	Intermediate Similarity	NPC471210
0.8167	Intermediate Similarity	NPC472634
0.8156	Intermediate Similarity	NPC473990
0.8156	Intermediate Similarity	NPC87317
0.8156	Intermediate Similarity	NPC74178
0.8156	Intermediate Similarity	NPC187792
0.8156	Intermediate Similarity	NPC95936
0.8156	Intermediate Similarity	NPC184755
0.8156	Intermediate Similarity	NPC250214
0.8154	Intermediate Similarity	NPC286135
0.8152	Intermediate Similarity	NPC279209
0.8152	Intermediate Similarity	NPC472276
0.8152	Intermediate Similarity	NPC476365
0.8152	Intermediate Similarity	NPC102277
0.8152	Intermediate Similarity	NPC105511
0.8146	Intermediate Similarity	NPC472455
0.8146	Intermediate Similarity	NPC5322
0.8146	Intermediate Similarity	NPC470328
0.8146	Intermediate Similarity	NPC6633
0.8146	Intermediate Similarity	NPC133970
0.8146	Intermediate Similarity	NPC472626
0.8146	Intermediate Similarity	NPC209614
0.8142	Intermediate Similarity	NPC229729
0.8142	Intermediate Similarity	NPC8965
0.8142	Intermediate Similarity	NPC218226
0.8142	Intermediate Similarity	NPC260266
0.8142	Intermediate Similarity	NPC243877
0.8142	Intermediate Similarity	NPC116745
0.8136	Intermediate Similarity	NPC192083
0.8136	Intermediate Similarity	NPC49402
0.8136	Intermediate Similarity	NPC70433
0.8136	Intermediate Similarity	NPC273462
0.8136	Intermediate Similarity	NPC280937
0.8136	Intermediate Similarity	NPC227337
0.8136	Intermediate Similarity	NPC472915
0.8136	Intermediate Similarity	NPC18727
0.8136	Intermediate Similarity	NPC33051
0.8136	Intermediate Similarity	NPC213896
0.8136	Intermediate Similarity	NPC469550
0.8132	Intermediate Similarity	NPC50960
0.8132	Intermediate Similarity	NPC239752
0.8132	Intermediate Similarity	NPC293319
0.8132	Intermediate Similarity	NPC234052
0.8132	Intermediate Similarity	NPC300053
0.8132	Intermediate Similarity	NPC108433
0.8132	Intermediate Similarity	NPC472450
0.8132	Intermediate Similarity	NPC25361
0.8132	Intermediate Similarity	NPC275780
0.8122	Intermediate Similarity	NPC261470
0.8122	Intermediate Similarity	NPC220912
0.8122	Intermediate Similarity	NPC471745
0.8122	Intermediate Similarity	NPC201800
0.8122	Intermediate Similarity	NPC81679
0.8122	Intermediate Similarity	NPC472635
0.8118	Intermediate Similarity	NPC108202
0.8111	Intermediate Similarity	NPC298093
0.8111	Intermediate Similarity	NPC471744
0.8111	Intermediate Similarity	NPC188433
0.8111	Intermediate Similarity	NPC475886
0.8111	Intermediate Similarity	NPC472624
0.8111	Intermediate Similarity	NPC476980
0.8111	Intermediate Similarity	NPC282009
0.8111	Intermediate Similarity	NPC174953
0.8111	Intermediate Similarity	NPC328102
0.8111	Intermediate Similarity	NPC474287
0.8111	Intermediate Similarity	NPC472630
0.8111	Intermediate Similarity	NPC204290
0.8111	Intermediate Similarity	NPC287328
0.8111	Intermediate Similarity	NPC470326
0.8111	Intermediate Similarity	NPC471973
0.8111	Intermediate Similarity	NPC472631
0.8111	Intermediate Similarity	NPC474960
0.8108	Intermediate Similarity	NPC205076
0.8108	Intermediate Similarity	NPC172807
0.8108	Intermediate Similarity	NPC48773
0.8108	Intermediate Similarity	NPC254540
0.8108	Intermediate Similarity	NPC472386
0.8108	Intermediate Similarity	NPC307518
0.8108	Intermediate Similarity	NPC211594
0.8108	Intermediate Similarity	NPC121333

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 NPC83019 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	669
0.2-0.3	1383
0.3-0.4	2287
0.4-0.5	2302
0.5-0.6	1465
0.6-0.7	633
0.7-0.8	196
0.8-0.85	5
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD7501	Clinical (unspecified phase)
0.8556	High Similarity	NPD4363	Phase 3
0.8556	High Similarity	NPD4360	Phase 2
0.8516	High Similarity	NPD4419	Clinical (unspecified phase)
0.8192	Intermediate Similarity	NPD5353	Approved
0.8136	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8122	Intermediate Similarity	NPD5710	Approved
0.8122	Intermediate Similarity	NPD5711	Approved
0.8111	Intermediate Similarity	NPD5494	Approved
0.8079	Intermediate Similarity	NPD1934	Approved
0.8077	Intermediate Similarity	NPD5242	Approved
0.8061	Intermediate Similarity	NPD5005	Approved
0.8061	Intermediate Similarity	NPD5006	Approved
0.8045	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD4361	Phase 2
0.8023	Intermediate Similarity	NPD5890	Approved
0.8023	Intermediate Similarity	NPD5889	Approved
0.8021	Intermediate Similarity	NPD7549	Discontinued
0.8	Intermediate Similarity	NPD7075	Discontinued
0.7989	Intermediate Similarity	NPD7473	Discontinued
0.7989	Intermediate Similarity	NPD3817	Phase 2
0.7966	Intermediate Similarity	NPD4380	Phase 2
0.7949	Intermediate Similarity	NPD4420	Approved
0.7946	Intermediate Similarity	NPD3818	Discontinued
0.7935	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6166	Phase 2
0.7933	Intermediate Similarity	NPD2801	Approved
0.7933	Intermediate Similarity	NPD7819	Suspended
0.7926	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD6232	Discontinued
0.7908	Intermediate Similarity	NPD8285	Discontinued
0.7903	Intermediate Similarity	NPD5844	Phase 1
0.7903	Intermediate Similarity	NPD7054	Approved
0.7865	Intermediate Similarity	NPD6585	Discontinued
0.7861	Intermediate Similarity	NPD7701	Phase 2
0.7861	Intermediate Similarity	NPD7472	Approved
0.7861	Intermediate Similarity	NPD7074	Phase 3
0.7833	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6386	Approved
0.7821	Intermediate Similarity	NPD7411	Suspended
0.7821	Intermediate Similarity	NPD6385	Approved
0.7802	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7038	Approved
0.7778	Intermediate Similarity	NPD6801	Discontinued
0.7778	Intermediate Similarity	NPD7039	Approved
0.7778	Intermediate Similarity	NPD6844	Discontinued
0.7751	Intermediate Similarity	NPD7907	Approved
0.7747	Intermediate Similarity	NPD3882	Suspended
0.774	Intermediate Similarity	NPD4111	Phase 1
0.774	Intermediate Similarity	NPD4665	Approved
0.7739	Intermediate Similarity	NPD2493	Approved
0.7739	Intermediate Similarity	NPD2494	Approved
0.7737	Intermediate Similarity	NPD7808	Phase 3
0.7725	Intermediate Similarity	NPD6797	Phase 2
0.7723	Intermediate Similarity	NPD7584	Approved
0.7716	Intermediate Similarity	NPD2974	Approved
0.7716	Intermediate Similarity	NPD2975	Approved
0.7716	Intermediate Similarity	NPD2973	Approved
0.7711	Intermediate Similarity	NPD4583	Approved
0.7711	Intermediate Similarity	NPD4582	Approved
0.7711	Intermediate Similarity	NPD8319	Approved
0.7711	Intermediate Similarity	NPD8320	Phase 1
0.7688	Intermediate Similarity	NPD4580	Approved
0.7685	Intermediate Similarity	NPD7585	Approved
0.7684	Intermediate Similarity	NPD7251	Discontinued
0.7684	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4002	Approved
0.7662	Intermediate Similarity	NPD4004	Approved
0.765	Intermediate Similarity	NPD3450	Approved
0.765	Intermediate Similarity	NPD3452	Approved
0.765	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD1465	Phase 2
0.7635	Intermediate Similarity	NPD7583	Approved
0.7632	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD1511	Approved
0.7619	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD5402	Approved
0.7594	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD6959	Discontinued
0.7573	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD7783	Phase 2
0.7566	Intermediate Similarity	NPD7177	Discontinued
0.7566	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD8151	Discontinued
0.7543	Intermediate Similarity	NPD1549	Phase 2
0.7542	Intermediate Similarity	NPD1512	Approved
0.7528	Intermediate Similarity	NPD7212	Phase 2
0.7528	Intermediate Similarity	NPD7213	Phase 3
0.7512	Intermediate Similarity	NPD4107	Approved
0.75	Intermediate Similarity	NPD6559	Discontinued
0.7488	Intermediate Similarity	NPD2899	Discontinued
0.7486	Intermediate Similarity	NPD7447	Phase 1
0.7486	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD919	Approved
0.7464	Intermediate Similarity	NPD7930	Approved
0.7463	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD2490	Approved
0.7462	Intermediate Similarity	NPD2488	Approved
0.746	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7768	Phase 2
0.7438	Intermediate Similarity	NPD3057	Approved
0.743	Intermediate Similarity	NPD6799	Approved
0.7429	Intermediate Similarity	NPD7047	Phase 3
0.7429	Intermediate Similarity	NPD2796	Approved
0.7426	Intermediate Similarity	NPD6777	Approved
0.7426	Intermediate Similarity	NPD6779	Approved
0.7426	Intermediate Similarity	NPD6781	Approved
0.7426	Intermediate Similarity	NPD6776	Approved
0.7426	Intermediate Similarity	NPD6778	Approved
0.7426	Intermediate Similarity	NPD6780	Approved
0.7426	Intermediate Similarity	NPD6782	Approved
0.7421	Intermediate Similarity	NPD3446	Phase 1
0.7418	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD5676	Approved
0.7403	Intermediate Similarity	NPD5403	Approved
0.7402	Intermediate Similarity	NPD7697	Approved
0.7402	Intermediate Similarity	NPD7696	Phase 3
0.7402	Intermediate Similarity	NPD7698	Approved
0.7391	Intermediate Similarity	NPD7577	Discontinued
0.7389	Intermediate Similarity	NPD4482	Phase 3
0.7383	Intermediate Similarity	NPD6997	Phase 2
0.7377	Intermediate Similarity	NPD6599	Discontinued
0.7376	Intermediate Similarity	NPD7048	Phase 3
0.7376	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD1510	Phase 2
0.7366	Intermediate Similarity	NPD7871	Phase 2
0.7366	Intermediate Similarity	NPD7870	Phase 2
0.736	Intermediate Similarity	NPD3750	Approved
0.7356	Intermediate Similarity	NPD7874	Approved
0.7356	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD6808	Phase 2
0.7353	Intermediate Similarity	NPD2972	Approved
0.7353	Intermediate Similarity	NPD2491	Approved
0.7353	Intermediate Similarity	NPD3533	Approved
0.7345	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5677	Discontinued
0.7337	Intermediate Similarity	NPD6873	Phase 2
0.7337	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2971	Approved
0.7333	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2968	Approved
0.733	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3749	Approved
0.7323	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7497	Discontinued
0.7317	Intermediate Similarity	NPD7435	Discontinued
0.7312	Intermediate Similarity	NPD5978	Approved
0.7312	Intermediate Similarity	NPD5977	Approved
0.731	Intermediate Similarity	NPD8150	Discontinued
0.7308	Intermediate Similarity	NPD7427	Discontinued
0.7302	Intermediate Similarity	NPD1247	Approved
0.7293	Intermediate Similarity	NPD5401	Approved
0.7293	Intermediate Similarity	NPD2533	Approved
0.7293	Intermediate Similarity	NPD2534	Approved
0.7293	Intermediate Similarity	NPD2532	Approved
0.7291	Intermediate Similarity	NPD7811	Phase 3
0.7291	Intermediate Similarity	NPD7810	Phase 3
0.7278	Intermediate Similarity	NPD6667	Approved
0.7278	Intermediate Similarity	NPD6666	Approved
0.7277	Intermediate Similarity	NPD4481	Phase 3
0.7277	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7906	Approved
0.7268	Intermediate Similarity	NPD3448	Approved
0.7259	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD4578	Approved
0.7245	Intermediate Similarity	NPD8312	Approved
0.7245	Intermediate Similarity	NPD8313	Approved
0.7245	Intermediate Similarity	NPD4577	Approved
0.7238	Intermediate Similarity	NPD7801	Approved
0.7232	Intermediate Similarity	NPD2935	Discontinued
0.7232	Intermediate Similarity	NPD6032	Approved
0.7228	Intermediate Similarity	NPD3226	Approved
0.7225	Intermediate Similarity	NPD3926	Phase 2
0.7222	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4663	Approved
0.7213	Intermediate Similarity	NPD920	Approved
0.7213	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD2654	Approved
0.7204	Intermediate Similarity	NPD37	Approved
0.72	Intermediate Similarity	NPD4622	Approved
0.72	Intermediate Similarity	NPD4618	Approved
0.7198	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD3146	Approved
0.7196	Intermediate Similarity	NPD6234	Discontinued
0.7189	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6823	Phase 2

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