NPASS Compound

Structure

NPC204580 OpenBabel07101718322D 36 39 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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 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 -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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 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 -6.0622 0.5000 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 -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 -6.9282 -0.0000 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 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 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 -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 27 1 0 0 0 0 3 32 1 0 0 0 0 4 33 1 0 0 0 0 5 34 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 27 1 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 14 1 0 0 0 0 10 20 2 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 27 1 0 0 0 0 13 35 1 0 0 0 0 14 26 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 28 2 0 0 0 0 17 22 1 0 0 0 0 17 29 1 0 0 0 0 18 23 2 0 0 0 0 18 30 1 0 0 0 0 19 24 2 0 0 0 0 19 32 1 0 0 0 0 20 24 1 0 0 0 0 20 33 1 0 0 0 0 21 36 1 1 0 0 0 22 25 2 0 0 0 0 23 25 1 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 31 2 0 0 0 0 26 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	499.18
Volume:	490.407
LogP:	3.125
LogD:	2.401
LogS:	-3.924
# Rotatable Bonds:	7
TPSA:	127.9
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.488
Synthetic Accessibility Score:	3.615
Fsp3:	0.385
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:	-4.914
MDCK Permeability:	3.8929567381273955e-05
Pgp-inhibitor:	0.599
Pgp-substrate:	0.172
Human Intestinal Absorption (HIA):	0.144
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.515
Plasma Protein Binding (PPB):	80.15619659423828%
Volume Distribution (VD):	1.52
Pgp-substrate:	27.455154418945312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.105
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.704
CYP2D6-inhibitor:	0.391
CYP2D6-substrate:	0.676
CYP3A4-inhibitor:	0.149
CYP3A4-substrate:	0.893

ADMET: Excretion

Clearance (CL):	8.706
Half-life (T1/2):	0.775

ADMET: Toxicity

hERG Blockers:	0.346
Human Hepatotoxicity (H-HT):	0.369
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.186
Rat Oral Acute Toxicity:	0.221
Maximum Recommended Daily Dose:	0.364
Skin Sensitization:	0.386
Carcinogencity:	0.084
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.818

Download Data

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

Natural Product: NPC204580

Natural Product ID:	NPC204580
*Common Name:**	Chrotacumine C
IUPAC Name:	[(3S,4R)-4-(5,7-dihydroxy-2-methyl-4-oxochromen-8-yl)-1-methylpiperidin-3-yl] 3,4,5-trimethoxybenzoate
Synonyms:	Chrotacumine C
Standard InCHIKey:	HVKVOCXJBCFWGR-YCRPNKLZSA-N
Standard InCHI:	InChI=1S/C26H29NO9/c1-13-8-16(28)23-18(30)11-17(29)22(25(23)35-13)15-6-7-27(2)12-21(15)36-26(31)14-9-19(32-3)24(34-5)20(10-14)33-4/h8-11,15,21,29-30H,6-7,12H2,1-5H3/t15-,21+/m0/s1
SMILES:	COc1cc(cc(c1OC)OC)C(=O)O[C@@H]1CN(C)CC[C@@H]1c1c(O)cc(c2c1oc(C)cc2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078324
PubChem CID:	44557091
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[523204]

☑ 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 NPC204580 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	299
0.1-0.2	1397
0.2-0.3	4082
0.3-0.4	10055
0.4-0.5	8059
0.5-0.6	5367
0.6-0.7	7283
0.7-0.8	5914
0.8-0.85	232
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	NPC83019
0.9253	High Similarity	NPC309692
0.9213	High Similarity	NPC469437
0.8914	High Similarity	NPC129578
0.8644	High Similarity	NPC207575
0.8644	High Similarity	NPC13481
0.8503	High Similarity	NPC264938
0.8407	Intermediate Similarity	NPC329816
0.8378	Intermediate Similarity	NPC18306
0.8371	Intermediate Similarity	NPC474150
0.8371	Intermediate Similarity	NPC474162
0.8352	Intermediate Similarity	NPC284820
0.8352	Intermediate Similarity	NPC108456
0.8352	Intermediate Similarity	NPC473272
0.8351	Intermediate Similarity	NPC314946
0.8343	Intermediate Similarity	NPC255807
0.8343	Intermediate Similarity	NPC31018
0.8333	Intermediate Similarity	NPC120593
0.8324	Intermediate Similarity	NPC474350
0.8324	Intermediate Similarity	NPC273959
0.8315	Intermediate Similarity	NPC473562
0.8315	Intermediate Similarity	NPC26326
0.8315	Intermediate Similarity	NPC134783
0.8278	Intermediate Similarity	NPC471788
0.8258	Intermediate Similarity	NPC119209
0.8258	Intermediate Similarity	NPC118256
0.8258	Intermediate Similarity	NPC192686
0.8258	Intermediate Similarity	NPC475784
0.8249	Intermediate Similarity	NPC129684
0.8249	Intermediate Similarity	NPC52889
0.8249	Intermediate Similarity	NPC291508
0.8249	Intermediate Similarity	NPC299520
0.8249	Intermediate Similarity	NPC181960
0.8242	Intermediate Similarity	NPC329992
0.8242	Intermediate Similarity	NPC288813
0.8239	Intermediate Similarity	NPC470327
0.8239	Intermediate Similarity	NPC45849
0.8239	Intermediate Similarity	NPC200761
0.8239	Intermediate Similarity	NPC477503
0.8239	Intermediate Similarity	NPC226025
0.8232	Intermediate Similarity	NPC128293
0.8222	Intermediate Similarity	NPC18100
0.8222	Intermediate Similarity	NPC186686
0.8218	Intermediate Similarity	NPC338131
0.8212	Intermediate Similarity	NPC471212
0.8212	Intermediate Similarity	NPC471211
0.8212	Intermediate Similarity	NPC266314
0.8212	Intermediate Similarity	NPC474186
0.8212	Intermediate Similarity	NPC474038
0.8202	Intermediate Similarity	NPC87317
0.8202	Intermediate Similarity	NPC117418
0.8202	Intermediate Similarity	NPC473990
0.8202	Intermediate Similarity	NPC53545
0.8202	Intermediate Similarity	NPC204879
0.8197	Intermediate Similarity	NPC103307
0.8196	Intermediate Similarity	NPC286135
0.8192	Intermediate Similarity	NPC278778
0.8192	Intermediate Similarity	NPC291878
0.8192	Intermediate Similarity	NPC209614
0.8192	Intermediate Similarity	NPC195796
0.8192	Intermediate Similarity	NPC470328
0.8192	Intermediate Similarity	NPC35038
0.8192	Intermediate Similarity	NPC472626
0.8187	Intermediate Similarity	NPC227683
0.8182	Intermediate Similarity	NPC475895
0.8182	Intermediate Similarity	NPC280937
0.8177	Intermediate Similarity	NPC62261
0.8177	Intermediate Similarity	NPC25361
0.8177	Intermediate Similarity	NPC472277
0.8167	Intermediate Similarity	NPC474034
0.8167	Intermediate Similarity	NPC229632
0.8167	Intermediate Similarity	NPC472448
0.8167	Intermediate Similarity	NPC474033
0.8167	Intermediate Similarity	NPC220912
0.8167	Intermediate Similarity	NPC83922
0.8167	Intermediate Similarity	NPC476247
0.8167	Intermediate Similarity	NPC81679
0.8156	Intermediate Similarity	NPC36217
0.8156	Intermediate Similarity	NPC475886
0.8156	Intermediate Similarity	NPC174953
0.8156	Intermediate Similarity	NPC292415
0.8156	Intermediate Similarity	NPC53889
0.8156	Intermediate Similarity	NPC477164
0.8156	Intermediate Similarity	NPC474287
0.8156	Intermediate Similarity	NPC299436
0.8156	Intermediate Similarity	NPC472630
0.8156	Intermediate Similarity	NPC472631
0.8156	Intermediate Similarity	NPC470326
0.8152	Intermediate Similarity	NPC212038
0.8152	Intermediate Similarity	NPC289396
0.8152	Intermediate Similarity	NPC475825
0.8152	Intermediate Similarity	NPC223375
0.8152	Intermediate Similarity	NPC81332
0.8152	Intermediate Similarity	NPC262580
0.8152	Intermediate Similarity	NPC475669
0.8152	Intermediate Similarity	NPC271848
0.8146	Intermediate Similarity	NPC262286
0.8146	Intermediate Similarity	NPC472598
0.8146	Intermediate Similarity	NPC36852
0.8146	Intermediate Similarity	NPC474055
0.8146	Intermediate Similarity	NPC474681
0.8146	Intermediate Similarity	NPC469584
0.8146	Intermediate Similarity	NPC27337
0.8146	Intermediate Similarity	NPC476981
0.8146	Intermediate Similarity	NPC217677
0.8146	Intermediate Similarity	NPC223787
0.8146	Intermediate Similarity	NPC218313
0.8146	Intermediate Similarity	NPC165977
0.8144	Intermediate Similarity	NPC316164
0.8142	Intermediate Similarity	NPC99613
0.8142	Intermediate Similarity	NPC49487
0.8142	Intermediate Similarity	NPC177480
0.8136	Intermediate Similarity	NPC117992
0.8136	Intermediate Similarity	NPC37392
0.8136	Intermediate Similarity	NPC230149
0.8136	Intermediate Similarity	NPC152951
0.8136	Intermediate Similarity	NPC472909
0.8136	Intermediate Similarity	NPC57674
0.8136	Intermediate Similarity	NPC168247
0.8132	Intermediate Similarity	NPC119589
0.8132	Intermediate Similarity	NPC272502
0.8132	Intermediate Similarity	NPC43319
0.8132	Intermediate Similarity	NPC173292
0.8132	Intermediate Similarity	NPC235610
0.8132	Intermediate Similarity	NPC171985
0.8132	Intermediate Similarity	NPC472452
0.8132	Intermediate Similarity	NPC320741
0.8125	Intermediate Similarity	NPC106976
0.8125	Intermediate Similarity	NPC471982
0.8125	Intermediate Similarity	NPC40033
0.8122	Intermediate Similarity	NPC205265
0.8122	Intermediate Similarity	NPC124038
0.8122	Intermediate Similarity	NPC472281
0.8122	Intermediate Similarity	NPC197168
0.8122	Intermediate Similarity	NPC41301
0.8122	Intermediate Similarity	NPC472625
0.8114	Intermediate Similarity	NPC180351
0.8111	Intermediate Similarity	NPC112418
0.8111	Intermediate Similarity	NPC471499
0.8111	Intermediate Similarity	NPC474187
0.8111	Intermediate Similarity	NPC289771
0.8111	Intermediate Similarity	NPC471210
0.8111	Intermediate Similarity	NPC472634
0.8111	Intermediate Similarity	NPC29876
0.8111	Intermediate Similarity	NPC475883
0.8111	Intermediate Similarity	NPC57715
0.8111	Intermediate Similarity	NPC228383
0.8111	Intermediate Similarity	NPC103201
0.8111	Intermediate Similarity	NPC97812
0.8111	Intermediate Similarity	NPC474351
0.8111	Intermediate Similarity	NPC165549
0.8111	Intermediate Similarity	NPC473106
0.8111	Intermediate Similarity	NPC234644
0.8111	Intermediate Similarity	NPC167678
0.8111	Intermediate Similarity	NPC472632
0.8111	Intermediate Similarity	NPC142252
0.8101	Intermediate Similarity	NPC95936
0.8101	Intermediate Similarity	NPC184755
0.8101	Intermediate Similarity	NPC250214
0.8101	Intermediate Similarity	NPC74178
0.8101	Intermediate Similarity	NPC187792
0.8098	Intermediate Similarity	NPC279209
0.8098	Intermediate Similarity	NPC472276
0.8098	Intermediate Similarity	NPC224462
0.8098	Intermediate Similarity	NPC476365
0.8098	Intermediate Similarity	NPC109827
0.8098	Intermediate Similarity	NPC102277
0.8098	Intermediate Similarity	NPC124470
0.8098	Intermediate Similarity	NPC105511
0.809	Intermediate Similarity	NPC88803
0.809	Intermediate Similarity	NPC472455
0.809	Intermediate Similarity	NPC133970
0.809	Intermediate Similarity	NPC291948
0.809	Intermediate Similarity	NPC104983
0.809	Intermediate Similarity	NPC300845
0.809	Intermediate Similarity	NPC6633
0.809	Intermediate Similarity	NPC250436
0.809	Intermediate Similarity	NPC5322
0.809	Intermediate Similarity	NPC138243
0.8087	Intermediate Similarity	NPC229729
0.8087	Intermediate Similarity	NPC260266
0.8087	Intermediate Similarity	NPC218226
0.8087	Intermediate Similarity	NPC117854
0.8087	Intermediate Similarity	NPC470456
0.8087	Intermediate Similarity	NPC243877
0.8087	Intermediate Similarity	NPC116745
0.8087	Intermediate Similarity	NPC477502
0.8087	Intermediate Similarity	NPC474024
0.8087	Intermediate Similarity	NPC6588
0.8087	Intermediate Similarity	NPC477154
0.8087	Intermediate Similarity	NPC8965
0.8079	Intermediate Similarity	NPC70433
0.8079	Intermediate Similarity	NPC298692
0.8079	Intermediate Similarity	NPC273462
0.8079	Intermediate Similarity	NPC49402
0.8079	Intermediate Similarity	NPC472915
0.8079	Intermediate Similarity	NPC18727
0.8079	Intermediate Similarity	NPC74924
0.8079	Intermediate Similarity	NPC213896
0.8079	Intermediate Similarity	NPC227337

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 NPC204580 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	663
0.2-0.3	1459
0.3-0.4	2343
0.4-0.5	2279
0.5-0.6	1421
0.6-0.7	589
0.7-0.8	183
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.877	High Similarity	NPD7501	Clinical (unspecified phase)
0.8503	High Similarity	NPD4360	Phase 2
0.8503	High Similarity	NPD4363	Phase 3
0.8462	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD5353	Approved
0.8167	Intermediate Similarity	NPD5710	Approved
0.8167	Intermediate Similarity	NPD5711	Approved
0.809	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD5494	Approved
0.8023	Intermediate Similarity	NPD1934	Approved
0.8022	Intermediate Similarity	NPD5242	Approved
0.801	Intermediate Similarity	NPD5005	Approved
0.801	Intermediate Similarity	NPD5006	Approved
0.7979	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD4361	Phase 2
0.7968	Intermediate Similarity	NPD7549	Discontinued
0.7966	Intermediate Similarity	NPD5890	Approved
0.7966	Intermediate Similarity	NPD5889	Approved
0.7944	Intermediate Similarity	NPD7075	Discontinued
0.7935	Intermediate Similarity	NPD7473	Discontinued
0.7933	Intermediate Similarity	NPD3817	Phase 2
0.791	Intermediate Similarity	NPD4380	Phase 2
0.7897	Intermediate Similarity	NPD4420	Approved
0.7892	Intermediate Similarity	NPD3818	Discontinued
0.788	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD6166	Phase 2
0.7877	Intermediate Similarity	NPD7819	Suspended
0.7877	Intermediate Similarity	NPD2801	Approved
0.7872	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD6232	Discontinued
0.7857	Intermediate Similarity	NPD8285	Discontinued
0.7849	Intermediate Similarity	NPD5844	Phase 1
0.7849	Intermediate Similarity	NPD7054	Approved
0.7811	Intermediate Similarity	NPD7701	Phase 2
0.7809	Intermediate Similarity	NPD6585	Discontinued
0.7807	Intermediate Similarity	NPD7074	Phase 3
0.7807	Intermediate Similarity	NPD7472	Approved
0.7778	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7411	Suspended
0.7765	Intermediate Similarity	NPD6385	Approved
0.7765	Intermediate Similarity	NPD6386	Approved
0.7747	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7039	Approved
0.7725	Intermediate Similarity	NPD7038	Approved
0.7722	Intermediate Similarity	NPD6844	Discontinued
0.7722	Intermediate Similarity	NPD6801	Discontinued
0.7703	Intermediate Similarity	NPD7907	Approved
0.7692	Intermediate Similarity	NPD4665	Approved
0.7692	Intermediate Similarity	NPD3882	Suspended
0.7692	Intermediate Similarity	NPD4111	Phase 1
0.7688	Intermediate Similarity	NPD2493	Approved
0.7688	Intermediate Similarity	NPD2494	Approved
0.7684	Intermediate Similarity	NPD7808	Phase 3
0.768	Intermediate Similarity	NPD1465	Phase 2
0.7673	Intermediate Similarity	NPD7584	Approved
0.7672	Intermediate Similarity	NPD6797	Phase 2
0.7672	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD2973	Approved
0.7665	Intermediate Similarity	NPD2974	Approved
0.7665	Intermediate Similarity	NPD2975	Approved
0.7662	Intermediate Similarity	NPD8319	Approved
0.7662	Intermediate Similarity	NPD8320	Phase 1
0.7662	Intermediate Similarity	NPD4582	Approved
0.7662	Intermediate Similarity	NPD4583	Approved
0.7638	Intermediate Similarity	NPD4580	Approved
0.7635	Intermediate Similarity	NPD7585	Approved
0.7632	Intermediate Similarity	NPD7251	Discontinued
0.7627	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6959	Discontinued
0.7614	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD4004	Approved
0.7612	Intermediate Similarity	NPD4002	Approved
0.7604	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3450	Approved
0.76	Intermediate Similarity	NPD3452	Approved
0.7598	Intermediate Similarity	NPD8151	Discontinued
0.7596	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7583	Approved
0.7571	Intermediate Similarity	NPD1511	Approved
0.7566	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD5402	Approved
0.7528	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD7783	Phase 2
0.7524	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7177	Discontinued
0.7486	Intermediate Similarity	NPD1512	Approved
0.7486	Intermediate Similarity	NPD1549	Phase 2
0.7472	Intermediate Similarity	NPD7213	Phase 3
0.7472	Intermediate Similarity	NPD7212	Phase 2
0.7463	Intermediate Similarity	NPD4107	Approved
0.7448	Intermediate Similarity	NPD6559	Discontinued
0.7441	Intermediate Similarity	NPD2899	Discontinued
0.743	Intermediate Similarity	NPD7447	Phase 1
0.7429	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD919	Approved
0.7416	Intermediate Similarity	NPD7930	Approved
0.7415	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD2490	Approved
0.7411	Intermediate Similarity	NPD2488	Approved
0.7407	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7768	Phase 2
0.7389	Intermediate Similarity	NPD3057	Approved
0.7386	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7047	Phase 3
0.7376	Intermediate Similarity	NPD6782	Approved
0.7376	Intermediate Similarity	NPD6779	Approved
0.7376	Intermediate Similarity	NPD6777	Approved
0.7376	Intermediate Similarity	NPD6776	Approved
0.7376	Intermediate Similarity	NPD6778	Approved
0.7376	Intermediate Similarity	NPD6780	Approved
0.7376	Intermediate Similarity	NPD6781	Approved
0.7374	Intermediate Similarity	NPD6799	Approved
0.7371	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD2796	Approved
0.7368	Intermediate Similarity	NPD3446	Phase 1
0.7363	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5676	Approved
0.7353	Intermediate Similarity	NPD7696	Phase 3
0.7353	Intermediate Similarity	NPD7697	Approved
0.7353	Intermediate Similarity	NPD7698	Approved
0.7348	Intermediate Similarity	NPD5403	Approved
0.734	Intermediate Similarity	NPD4482	Phase 3
0.7337	Intermediate Similarity	NPD7577	Discontinued
0.7336	Intermediate Similarity	NPD6997	Phase 2
0.7333	Intermediate Similarity	NPD2534	Approved
0.7333	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD2533	Approved
0.733	Intermediate Similarity	NPD7048	Phase 3
0.7322	Intermediate Similarity	NPD6599	Discontinued
0.7317	Intermediate Similarity	NPD7871	Phase 2
0.7317	Intermediate Similarity	NPD7870	Phase 2
0.7314	Intermediate Similarity	NPD1510	Phase 2
0.7308	Intermediate Similarity	NPD7874	Approved
0.7308	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD2491	Approved
0.7304	Intermediate Similarity	NPD3533	Approved
0.7304	Intermediate Similarity	NPD2972	Approved
0.7303	Intermediate Similarity	NPD3750	Approved
0.7302	Intermediate Similarity	NPD6808	Phase 2
0.7287	Intermediate Similarity	NPD5677	Discontinued
0.7283	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6873	Phase 2
0.7282	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD2971	Approved
0.7282	Intermediate Similarity	NPD2968	Approved
0.7282	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3749	Approved
0.7273	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7497	Discontinued
0.7268	Intermediate Similarity	NPD7435	Discontinued
0.7259	Intermediate Similarity	NPD8150	Discontinued
0.7258	Intermediate Similarity	NPD5978	Approved
0.7258	Intermediate Similarity	NPD5977	Approved
0.7253	Intermediate Similarity	NPD7427	Discontinued
0.7249	Intermediate Similarity	NPD1247	Approved
0.7247	Intermediate Similarity	NPD2654	Approved
0.7243	Intermediate Similarity	NPD37	Approved
0.7241	Intermediate Similarity	NPD7810	Phase 3
0.7241	Intermediate Similarity	NPD7811	Phase 3
0.7238	Intermediate Similarity	NPD5401	Approved
0.7234	Intermediate Similarity	NPD6234	Discontinued
0.7225	Intermediate Similarity	NPD4481	Phase 3
0.7225	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7906	Approved
0.7222	Intermediate Similarity	NPD6666	Approved
0.7222	Intermediate Similarity	NPD6667	Approved
0.722	Intermediate Similarity	NPD3448	Approved
0.7219	Intermediate Similarity	NPD4966	Approved
0.7219	Intermediate Similarity	NPD4967	Phase 2
0.7219	Intermediate Similarity	NPD4965	Approved
0.7216	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6625	Approved
0.7194	Intermediate Similarity	NPD4577	Approved
0.7194	Intermediate Similarity	NPD8313	Approved
0.7194	Intermediate Similarity	NPD8312	Approved
0.7194	Intermediate Similarity	NPD4578	Approved
0.719	Intermediate Similarity	NPD7801	Approved
0.7175	Intermediate Similarity	NPD2935	Discontinued
0.7175	Intermediate Similarity	NPD6032	Approved
0.7174	Intermediate Similarity	NPD3226	Approved
0.7173	Intermediate Similarity	NPD3926	Phase 2
0.7172	Intermediate Similarity	NPD4663	Approved
0.7167	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD920	Approved
0.7151	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD4622	Approved
0.7143	Intermediate Similarity	NPD4618	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