NPASS Compound

Structure

NPC472823 OpenBabel07101718272D 25 29 0 0 1 0 0 0 0 0999 V2000 -1.2990 2.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8482 1.9410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1651 0.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4330 1.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4360 2.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1651 3.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 0.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8971 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 1.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0311 3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2990 1.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8971 3.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1651 2.2500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2990 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4330 0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 4.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4150 0.9390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8482 3.5590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 5 1 0 0 0 0 2 13 1 0 0 0 0 3 6 1 0 0 0 0 3 15 1 0 0 0 0 4 7 2 0 0 0 0 4 12 1 0 0 0 0 6 19 1 0 0 0 0 7 25 1 0 0 0 0 8 14 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 9 19 1 0 0 0 0 10 18 1 0 0 0 0 10 20 1 0 0 0 0 11 20 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 6 0 0 0 14 16 1 0 0 0 0 14 22 2 0 0 0 0 15 17 1 6 0 0 0 15 18 1 0 0 0 0 16 25 1 0 0 0 0 17 1 1 6 0 0 0 18 5 1 6 0 0 0 19 20 1 6 0 0 0 19 23 1 0 0 0 0 20 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.18
Volume:	347.736
LogP:	1.56
LogD:	1.834
LogS:	-3.28
# Rotatable Bonds:	1
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.726
Synthetic Accessibility Score:	6.2
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.823
MDCK Permeability:	1.137142135121394e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.904
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.78
30% Bioavailability (F30%):	0.883

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.483
Plasma Protein Binding (PPB):	85.62725830078125%
Volume Distribution (VD):	0.748
Pgp-substrate:	16.576427459716797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.421
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.967
CYP3A4-substrate:	0.24

ADMET: Excretion

Clearance (CL):	7.867
Half-life (T1/2):	0.412

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.755
Drug-inuced Liver Injury (DILI):	0.077
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.884
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.106
Carcinogencity:	0.991
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC472823

Natural Product ID:	NPC472823
*Common Name:**	YDESRUMIEMCEJF-WCQUAJJMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YDESRUMIEMCEJF-WCQUAJJMSA-N
Standard InCHI:	InChI=1S/C20H26O5/c1-17-8-14(22)16-12(4-7-25-16)13(17)2-5-18-9-19(23,6-3-15(17)18)20(24,10-18)11-21/h4,7,13,15,21,23-24H,2-3,5-6,8-11H2,1H3/t13-,15+,17-,18+,19-,20+/m1/s1
SMILES:	CC12CC(=O)C3=C(C1CCC45C2CCC(C4)(C(C5)(CO)O)O)C=CO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586290
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO32576	tricalysia fruticosa	Species	Rubiaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[26052978]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[515141]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	>	90.0	%	PMID[515141]

☑ 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 NPC472823 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	387
0.1-0.2	1375
0.2-0.3	2762
0.3-0.4	5552
0.4-0.5	11794
0.5-0.6	8890
0.6-0.7	10173
0.7-0.8	1536
0.8-0.85	193
0.85-0.9	33
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8742	High Similarity	NPC263337
0.8654	High Similarity	NPC228842
0.8634	High Similarity	NPC18986
0.858	High Similarity	NPC283209
0.8562	High Similarity	NPC194499
0.8562	High Similarity	NPC304692
0.8544	High Similarity	NPC121615
0.8544	High Similarity	NPC470996
0.8544	High Similarity	NPC294511
0.8537	High Similarity	NPC472784
0.8535	High Similarity	NPC212257
0.85	High Similarity	NPC104736
0.8476	Intermediate Similarity	NPC121995
0.8466	Intermediate Similarity	NPC285567
0.8462	Intermediate Similarity	NPC302987
0.8457	Intermediate Similarity	NPC287559
0.8452	Intermediate Similarity	NPC167340
0.8447	Intermediate Similarity	NPC88007
0.8442	Intermediate Similarity	NPC243577
0.8438	Intermediate Similarity	NPC472785
0.8434	Intermediate Similarity	NPC44602
0.8428	Intermediate Similarity	NPC246164
0.8421	Intermediate Similarity	NPC202260
0.8405	Intermediate Similarity	NPC472782
0.8405	Intermediate Similarity	NPC472781
0.8405	Intermediate Similarity	NPC68848
0.8405	Intermediate Similarity	NPC79571
0.8395	Intermediate Similarity	NPC140952
0.8395	Intermediate Similarity	NPC116639
0.8395	Intermediate Similarity	NPC84349
0.8385	Intermediate Similarity	NPC41880
0.8365	Intermediate Similarity	NPC472787
0.8364	Intermediate Similarity	NPC475779
0.8354	Intermediate Similarity	NPC472783
0.8354	Intermediate Similarity	NPC14499
0.8354	Intermediate Similarity	NPC475039
0.8354	Intermediate Similarity	NPC470998
0.8354	Intermediate Similarity	NPC476035
0.8354	Intermediate Similarity	NPC472780
0.8344	Intermediate Similarity	NPC216755
0.8344	Intermediate Similarity	NPC8389
0.8333	Intermediate Similarity	NPC7059
0.8333	Intermediate Similarity	NPC185456
0.8333	Intermediate Similarity	NPC81405
0.8333	Intermediate Similarity	NPC195954
0.8323	Intermediate Similarity	NPC472786
0.8323	Intermediate Similarity	NPC75310
0.8323	Intermediate Similarity	NPC92979
0.8323	Intermediate Similarity	NPC88958
0.8303	Intermediate Similarity	NPC261184
0.8302	Intermediate Similarity	NPC196846
0.8294	Intermediate Similarity	NPC478177
0.8293	Intermediate Similarity	NPC197596
0.8291	Intermediate Similarity	NPC471007
0.8289	Intermediate Similarity	NPC307401
0.8284	Intermediate Similarity	NPC471437
0.8274	Intermediate Similarity	NPC285227
0.8266	Intermediate Similarity	NPC105395
0.825	Intermediate Similarity	NPC272590
0.8247	Intermediate Similarity	NPC90296
0.8242	Intermediate Similarity	NPC663
0.8242	Intermediate Similarity	NPC224394
0.8228	Intermediate Similarity	NPC471174
0.8228	Intermediate Similarity	NPC71821
0.8217	Intermediate Similarity	NPC245522
0.8217	Intermediate Similarity	NPC114513
0.8217	Intermediate Similarity	NPC5676
0.8214	Intermediate Similarity	NPC470995
0.8204	Intermediate Similarity	NPC478179
0.8204	Intermediate Similarity	NPC310572
0.8199	Intermediate Similarity	NPC475777
0.8193	Intermediate Similarity	NPC56358
0.8187	Intermediate Similarity	NPC470997
0.8182	Intermediate Similarity	NPC188649
0.8182	Intermediate Similarity	NPC263432
0.8176	Intermediate Similarity	NPC236004
0.8176	Intermediate Similarity	NPC93666
0.8171	Intermediate Similarity	NPC474611
0.8165	Intermediate Similarity	NPC478166
0.8161	Intermediate Similarity	NPC247563
0.8161	Intermediate Similarity	NPC242068
0.8158	Intermediate Similarity	NPC476947
0.8148	Intermediate Similarity	NPC302054
0.8148	Intermediate Similarity	NPC253201
0.8148	Intermediate Similarity	NPC34421
0.8148	Intermediate Similarity	NPC98206
0.8148	Intermediate Similarity	NPC237259
0.8144	Intermediate Similarity	NPC277618
0.8144	Intermediate Similarity	NPC478178
0.8133	Intermediate Similarity	NPC477405
0.8133	Intermediate Similarity	NPC288602
0.8133	Intermediate Similarity	NPC88841
0.8129	Intermediate Similarity	NPC148374
0.8129	Intermediate Similarity	NPC67003
0.8125	Intermediate Similarity	NPC234494
0.8121	Intermediate Similarity	NPC470789
0.8118	Intermediate Similarity	NPC469848
0.8117	Intermediate Similarity	NPC471996
0.8107	Intermediate Similarity	NPC118086
0.8107	Intermediate Similarity	NPC88593
0.8105	Intermediate Similarity	NPC46896
0.8098	Intermediate Similarity	NPC296807
0.8098	Intermediate Similarity	NPC155939
0.8098	Intermediate Similarity	NPC141538
0.8098	Intermediate Similarity	NPC25351
0.8095	Intermediate Similarity	NPC270312
0.8095	Intermediate Similarity	NPC472282
0.8095	Intermediate Similarity	NPC476861
0.8095	Intermediate Similarity	NPC473753
0.8095	Intermediate Similarity	NPC473766
0.8095	Intermediate Similarity	NPC476850
0.8086	Intermediate Similarity	NPC471613
0.8086	Intermediate Similarity	NPC472672
0.8086	Intermediate Similarity	NPC33938
0.8084	Intermediate Similarity	NPC476858
0.8084	Intermediate Similarity	NPC476856
0.8084	Intermediate Similarity	NPC123088
0.8084	Intermediate Similarity	NPC276551
0.8084	Intermediate Similarity	NPC476857
0.8081	Intermediate Similarity	NPC472665
0.8079	Intermediate Similarity	NPC473982
0.8072	Intermediate Similarity	NPC5741
0.8072	Intermediate Similarity	NPC329938
0.8072	Intermediate Similarity	NPC69028
0.8072	Intermediate Similarity	NPC472767
0.807	Intermediate Similarity	NPC471632
0.807	Intermediate Similarity	NPC469576
0.807	Intermediate Similarity	NPC94763
0.8061	Intermediate Similarity	NPC473368
0.8061	Intermediate Similarity	NPC475967
0.8059	Intermediate Similarity	NPC159232
0.8059	Intermediate Similarity	NPC475237
0.8059	Intermediate Similarity	NPC475641
0.805	Intermediate Similarity	NPC233763
0.8049	Intermediate Similarity	NPC478161
0.8049	Intermediate Similarity	NPC478159
0.8047	Intermediate Similarity	NPC296558
0.8047	Intermediate Similarity	NPC472766
0.8047	Intermediate Similarity	NPC242334
0.8047	Intermediate Similarity	NPC472765
0.8037	Intermediate Similarity	NPC282793
0.8036	Intermediate Similarity	NPC149945
0.8036	Intermediate Similarity	NPC23387
0.8036	Intermediate Similarity	NPC470875
0.8026	Intermediate Similarity	NPC218838
0.8025	Intermediate Similarity	NPC52412
0.8024	Intermediate Similarity	NPC469338
0.8024	Intermediate Similarity	NPC292389
0.8023	Intermediate Similarity	NPC469633
0.8012	Intermediate Similarity	NPC69647
0.8012	Intermediate Similarity	NPC125182
0.8012	Intermediate Similarity	NPC472654
0.8012	Intermediate Similarity	NPC280025
0.8012	Intermediate Similarity	NPC477402
0.8012	Intermediate Similarity	NPC211625
0.8012	Intermediate Similarity	NPC335761
0.8012	Intermediate Similarity	NPC25255
0.8	Intermediate Similarity	NPC224418
0.8	Intermediate Similarity	NPC59502
0.8	Intermediate Similarity	NPC197137
0.8	Intermediate Similarity	NPC472659
0.7988	Intermediate Similarity	NPC472764
0.7988	Intermediate Similarity	NPC472774
0.7988	Intermediate Similarity	NPC476853
0.7988	Intermediate Similarity	NPC214541
0.7988	Intermediate Similarity	NPC469966
0.7988	Intermediate Similarity	NPC179170
0.7988	Intermediate Similarity	NPC472775
0.7988	Intermediate Similarity	NPC44675
0.7987	Intermediate Similarity	NPC56731
0.7976	Intermediate Similarity	NPC476860
0.7976	Intermediate Similarity	NPC469849
0.7976	Intermediate Similarity	NPC472664
0.7976	Intermediate Similarity	NPC470940
0.7975	Intermediate Similarity	NPC145830
0.7975	Intermediate Similarity	NPC476946
0.7975	Intermediate Similarity	NPC75906
0.7964	Intermediate Similarity	NPC5079
0.7964	Intermediate Similarity	NPC470792
0.7964	Intermediate Similarity	NPC6326
0.7964	Intermediate Similarity	NPC193798
0.7964	Intermediate Similarity	NPC471003
0.7964	Intermediate Similarity	NPC471167
0.7964	Intermediate Similarity	NPC471166
0.7952	Intermediate Similarity	NPC477403
0.7952	Intermediate Similarity	NPC123153
0.7952	Intermediate Similarity	NPC299094
0.7952	Intermediate Similarity	NPC10051
0.7941	Intermediate Similarity	NPC471397
0.7941	Intermediate Similarity	NPC255787
0.7941	Intermediate Similarity	NPC271235
0.7941	Intermediate Similarity	NPC160651
0.7937	Intermediate Similarity	NPC470999
0.7933	Intermediate Similarity	NPC26532
0.7931	Intermediate Similarity	NPC11062
0.7929	Intermediate Similarity	NPC214600
0.7927	Intermediate Similarity	NPC178932
0.7927	Intermediate Similarity	NPC114880
0.7925	Intermediate Similarity	NPC199044
0.7925	Intermediate Similarity	NPC238843

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 NPC472823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	833
0.2-0.3	1651
0.3-0.4	2675
0.4-0.5	2162
0.5-0.6	1120
0.6-0.7	346
0.7-0.8	23
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8452	Intermediate Similarity	NPD6764	Approved
0.8452	Intermediate Similarity	NPD6765	Approved
0.8438	Intermediate Similarity	NPD5760	Phase 2
0.8438	Intermediate Similarity	NPD5761	Phase 2
0.8256	Intermediate Similarity	NPD6784	Approved
0.8256	Intermediate Similarity	NPD6785	Approved
0.7898	Intermediate Similarity	NPD8434	Phase 2
0.7798	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6273	Approved
0.7702	Intermediate Similarity	NPD7236	Approved
0.761	Intermediate Similarity	NPD1471	Phase 3
0.7516	Intermediate Similarity	NPD5735	Approved
0.75	Intermediate Similarity	NPD5762	Approved
0.75	Intermediate Similarity	NPD5763	Approved
0.747	Intermediate Similarity	NPD7239	Suspended
0.7469	Intermediate Similarity	NPD4628	Phase 3
0.7407	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7799	Discontinued
0.7381	Intermediate Similarity	NPD6599	Discontinued
0.7299	Intermediate Similarity	NPD8127	Discontinued
0.7284	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7028	Phase 2
0.7251	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4140	Approved
0.7216	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7186	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7057	Phase 3
0.7168	Intermediate Similarity	NPD3882	Suspended
0.7168	Intermediate Similarity	NPD7058	Phase 2
0.7158	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6353	Approved
0.7127	Intermediate Similarity	NPD6559	Discontinued
0.7126	Intermediate Similarity	NPD7075	Discontinued
0.7126	Intermediate Similarity	NPD6799	Approved
0.7118	Intermediate Similarity	NPD3226	Approved
0.711	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD1247	Approved
0.7102	Intermediate Similarity	NPD7199	Phase 2
0.7093	Intermediate Similarity	NPD6801	Discontinued
0.7083	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6002	Phase 3
0.7073	Intermediate Similarity	NPD6005	Phase 3
0.7073	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6004	Phase 3
0.7073	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD8032	Phase 2
0.7052	Intermediate Similarity	NPD7819	Suspended
0.7051	Intermediate Similarity	NPD1876	Approved
0.7044	Intermediate Similarity	NPD7095	Approved
0.7035	Intermediate Similarity	NPD7411	Suspended
0.7018	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7458	Discontinued
0.7012	Intermediate Similarity	NPD6099	Approved
0.7012	Intermediate Similarity	NPD6100	Approved
0.7011	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6798	Discontinued
0.7	Intermediate Similarity	NPD3268	Approved
0.6989	Remote Similarity	NPD919	Approved
0.6987	Remote Similarity	NPD5327	Phase 3
0.6974	Remote Similarity	NPD9092	Discovery
0.697	Remote Similarity	NPD2344	Approved
0.6962	Remote Similarity	NPD4624	Approved
0.6959	Remote Similarity	NPD7497	Discontinued
0.6954	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2799	Discontinued
0.6946	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7003	Approved
0.6932	Remote Similarity	NPD3749	Approved
0.6923	Remote Similarity	NPD3972	Approved
0.6914	Remote Similarity	NPD3817	Phase 2
0.6909	Remote Similarity	NPD2796	Approved
0.6903	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5403	Approved
0.6889	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6166	Phase 2
0.6882	Remote Similarity	NPD5401	Approved
0.6882	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4380	Phase 2
0.6868	Remote Similarity	NPD5844	Phase 1
0.6867	Remote Similarity	NPD2346	Discontinued
0.6855	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5494	Approved
0.6852	Remote Similarity	NPD6233	Phase 2
0.6852	Remote Similarity	NPD6663	Approved
0.6848	Remote Similarity	NPD7685	Pre-registration
0.6845	Remote Similarity	NPD3750	Approved
0.6826	Remote Similarity	NPD1549	Phase 2
0.6821	Remote Similarity	NPD3057	Approved
0.6818	Remote Similarity	NPD5402	Approved
0.6813	Remote Similarity	NPD2163	Approved
0.681	Remote Similarity	NPD4060	Phase 1
0.681	Remote Similarity	NPD3620	Phase 2
0.681	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2354	Approved
0.6805	Remote Similarity	NPD2309	Approved
0.6802	Remote Similarity	NPD920	Approved
0.68	Remote Similarity	NPD1934	Approved
0.6798	Remote Similarity	NPD8404	Phase 2
0.6796	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3267	Approved
0.6792	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3266	Approved
0.6792	Remote Similarity	NPD3094	Phase 2
0.679	Remote Similarity	NPD3764	Approved
0.6789	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3092	Approved
0.675	Remote Similarity	NPD5647	Approved
0.675	Remote Similarity	NPD2798	Approved
0.6747	Remote Similarity	NPD3748	Approved
0.6747	Remote Similarity	NPD1510	Phase 2
0.6747	Remote Similarity	NPD7033	Discontinued
0.6747	Remote Similarity	NPD4308	Phase 3
0.6746	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8166	Discontinued
0.6746	Remote Similarity	NPD4110	Phase 3
0.6744	Remote Similarity	NPD5049	Phase 3
0.6744	Remote Similarity	NPD1512	Approved
0.6742	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.674	Remote Similarity	NPD3926	Phase 2
0.6735	Remote Similarity	NPD3533	Approved
0.6735	Remote Similarity	NPD2972	Approved
0.6731	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3019	Approved
0.6728	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6653	Approved
0.6725	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6959	Discontinued
0.6721	Remote Similarity	NPD3751	Discontinued
0.6721	Remote Similarity	NPD3818	Discontinued
0.6709	Remote Similarity	NPD1608	Approved
0.6708	Remote Similarity	NPD5736	Approved
0.6707	Remote Similarity	NPD1551	Phase 2
0.6706	Remote Similarity	NPD3887	Approved
0.6687	Remote Similarity	NPD2313	Discontinued
0.6687	Remote Similarity	NPD2797	Approved
0.6686	Remote Similarity	NPD2800	Approved
0.6686	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3787	Discontinued
0.6685	Remote Similarity	NPD4966	Approved
0.6685	Remote Similarity	NPD4965	Approved
0.6685	Remote Similarity	NPD4967	Phase 2
0.6685	Remote Similarity	NPD7768	Phase 2
0.6684	Remote Similarity	NPD8312	Approved
0.6684	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD2801	Approved
0.665	Remote Similarity	NPD2491	Approved
0.6646	Remote Similarity	NPD7961	Discontinued
0.6646	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD1511	Approved
0.6627	Remote Similarity	NPD5958	Discontinued
0.6627	Remote Similarity	NPD4534	Discontinued
0.6627	Remote Similarity	NPD2424	Discontinued
0.6627	Remote Similarity	NPD1607	Approved
0.6624	Remote Similarity	NPD2932	Approved
0.6613	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6797	Phase 2
0.6611	Remote Similarity	NPD6234	Discontinued
0.661	Remote Similarity	NPD37	Approved
0.6609	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2935	Discontinued
0.6606	Remote Similarity	NPD4307	Phase 2
0.6606	Remote Similarity	NPD1240	Approved
0.6601	Remote Similarity	NPD1241	Discontinued
0.659	Remote Similarity	NPD2532	Approved
0.659	Remote Similarity	NPD2534	Approved
0.659	Remote Similarity	NPD2533	Approved
0.6588	Remote Similarity	NPD1243	Approved
0.6585	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD3026	Approved
0.6582	Remote Similarity	NPD3023	Approved
0.6578	Remote Similarity	NPD7251	Discontinued
0.6576	Remote Similarity	NPD7473	Discontinued
0.6568	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD2353	Approved
0.6566	Remote Similarity	NPD3448	Approved
0.6564	Remote Similarity	NPD6832	Phase 2
0.6562	Remote Similarity	NPD2490	Approved
0.6562	Remote Similarity	NPD2488	Approved
0.6561	Remote Similarity	NPD3024	Approved
0.6561	Remote Similarity	NPD3025	Approved
0.6552	Remote Similarity	NPD5676	Approved
0.6548	Remote Similarity	NPD4107	Approved
0.6545	Remote Similarity	NPD4062	Phase 3
0.6543	Remote Similarity	NPD7808	Phase 3
0.6543	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7177	Discontinued
0.6534	Remote Similarity	NPD2651	Approved
0.6534	Remote Similarity	NPD2649	Approved
0.6529	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2403	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