NPASS Compound

Structure

NPC231751 OpenBabel07101718192D 24 28 0 0 1 0 0 0 0 0999 V2000 3.5491 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 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 4.4152 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9821 3.5590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7142 4.0590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8482 3.5590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5802 3.5590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8482 4.5590 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 2 3 1 0 0 0 0 2 12 1 0 0 0 0 3 16 1 0 0 0 0 4 7 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 6 18 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 19 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 20 1 6 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 18 1 1 0 0 0 15 5 1 1 0 0 0 15 24 1 0 0 0 0 16 18 1 1 0 0 0 16 19 1 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 1 1 1 0 0 0 19 7 1 1 0 0 0 20 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	341.582
LogP:	2.927
LogD:	2.694
LogS:	-4.419
# Rotatable Bonds:	1
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.737
Synthetic Accessibility Score:	6.028
Fsp3:	0.8
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:	-5.514
MDCK Permeability:	6.155437858978985e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.155
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.533
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	96.9205093383789%
Volume Distribution (VD):	1.411
Pgp-substrate:	3.7345166206359863%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.744
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.62
CYP2C9-inhibitor:	0.098
CYP2C9-substrate:	0.318
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.482
CYP3A4-inhibitor:	0.846
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	11.236
Half-life (T1/2):	0.554

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.711
Drug-inuced Liver Injury (DILI):	0.086
AMES Toxicity:	0.103
Rat Oral Acute Toxicity:	0.397
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.156
Carcinogencity:	0.562
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC231751

Natural Product ID:	NPC231751
*Common Name:**	GCGHKCGNVBKLKA-IZAYAAFUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GCGHKCGNVBKLKA-IZAYAAFUSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-18-6-5-15-13(8-17(22)24-15)14(18)4-7-19-9-12(2-3-16(18)19)20(23,10-19)11-21/h8,12,14-16,21,23H,2-7,9-11H2,1H3/t12-,14-,15-,16+,18-,19+,20+/m1/s1
SMILES:	C[C@@]12CC[C@@H]3C(=CC(=O)O3)[C@H]1CC[C@]13C[C@@H](CC[C@@H]23)[C@](C1)(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586293
PubChem CID:	11595156
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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[525863]
NPT113	Cell Line	RAW264.7	Mus musculus	Survival	>	90.0	%	PMID[525863]

☑ 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 NPC231751 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	187
0.1-0.2	1264
0.2-0.3	4523
0.3-0.4	13527
0.4-0.5	8461
0.5-0.6	6212
0.6-0.7	5956
0.7-0.8	2350
0.8-0.85	171
0.85-0.9	23
0.9-0.95	20
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.957	High Similarity	NPC472826
0.9474	High Similarity	NPC472821
0.9278	High Similarity	NPC472818
0.9278	High Similarity	NPC186668
0.9263	High Similarity	NPC268829
0.9263	High Similarity	NPC247701
0.9263	High Similarity	NPC222875
0.9263	High Similarity	NPC25177
0.9263	High Similarity	NPC295110
0.9184	High Similarity	NPC472820
0.9175	High Similarity	NPC472819
0.9072	High Similarity	NPC97487
0.9072	High Similarity	NPC196471
0.9072	High Similarity	NPC189588
0.9072	High Similarity	NPC10232
0.9072	High Similarity	NPC187302
0.9072	High Similarity	NPC160583
0.9053	High Similarity	NPC181147
0.8889	High Similarity	NPC119855
0.8889	High Similarity	NPC220217
0.883	High Similarity	NPC201725
0.8788	High Similarity	NPC200861
0.8788	High Similarity	NPC472822
0.8687	High Similarity	NPC112009
0.8627	High Similarity	NPC475030
0.8571	High Similarity	NPC69576
0.8571	High Similarity	NPC201406
0.8571	High Similarity	NPC471633
0.8571	High Similarity	NPC31354
0.8571	High Similarity	NPC84949
0.8557	High Similarity	NPC210337
0.8511	High Similarity	NPC302280
0.85	High Similarity	NPC171014
0.85	High Similarity	NPC180204
0.8491	Intermediate Similarity	NPC193382
0.8491	Intermediate Similarity	NPC199428
0.8491	Intermediate Similarity	NPC5311
0.8491	Intermediate Similarity	NPC196931
0.8491	Intermediate Similarity	NPC310341
0.8491	Intermediate Similarity	NPC99620
0.8478	Intermediate Similarity	NPC131813
0.8454	Intermediate Similarity	NPC88009
0.8431	Intermediate Similarity	NPC43063
0.8431	Intermediate Similarity	NPC79298
0.8421	Intermediate Similarity	NPC329842
0.8411	Intermediate Similarity	NPC27507
0.8411	Intermediate Similarity	NPC196429
0.8411	Intermediate Similarity	NPC84987
0.8411	Intermediate Similarity	NPC471354
0.8411	Intermediate Similarity	NPC244402
0.8411	Intermediate Similarity	NPC152615
0.8411	Intermediate Similarity	NPC142066
0.8411	Intermediate Similarity	NPC309034
0.8411	Intermediate Similarity	NPC158344
0.8411	Intermediate Similarity	NPC290693
0.8411	Intermediate Similarity	NPC471351
0.8411	Intermediate Similarity	NPC87250
0.8411	Intermediate Similarity	NPC93883
0.8411	Intermediate Similarity	NPC471355
0.8411	Intermediate Similarity	NPC157376
0.8411	Intermediate Similarity	NPC99728
0.8411	Intermediate Similarity	NPC50305
0.8411	Intermediate Similarity	NPC471353
0.8411	Intermediate Similarity	NPC473852
0.8411	Intermediate Similarity	NPC474418
0.8411	Intermediate Similarity	NPC34390
0.8411	Intermediate Similarity	NPC77319
0.8411	Intermediate Similarity	NPC243196
0.8384	Intermediate Similarity	NPC473510
0.8384	Intermediate Similarity	NPC230546
0.8384	Intermediate Similarity	NPC251680
0.837	Intermediate Similarity	NPC474013
0.8351	Intermediate Similarity	NPC329435
0.835	Intermediate Similarity	NPC472825
0.8333	Intermediate Similarity	NPC83287
0.8333	Intermediate Similarity	NPC295843
0.8333	Intermediate Similarity	NPC53555
0.8316	Intermediate Similarity	NPC78973
0.83	Intermediate Similarity	NPC11974
0.8283	Intermediate Similarity	NPC218107
0.8269	Intermediate Similarity	NPC75389
0.8257	Intermediate Similarity	NPC292467
0.8257	Intermediate Similarity	NPC32177
0.8257	Intermediate Similarity	NPC470897
0.8257	Intermediate Similarity	NPC55532
0.8257	Intermediate Similarity	NPC30483
0.8257	Intermediate Similarity	NPC44899
0.8257	Intermediate Similarity	NPC5883
0.8257	Intermediate Similarity	NPC469756
0.8257	Intermediate Similarity	NPC236973
0.8257	Intermediate Similarity	NPC329905
0.8257	Intermediate Similarity	NPC29639
0.8257	Intermediate Similarity	NPC304260
0.8252	Intermediate Similarity	NPC131665
0.8252	Intermediate Similarity	NPC255387
0.8247	Intermediate Similarity	NPC105490
0.8241	Intermediate Similarity	NPC203862
0.8229	Intermediate Similarity	NPC234335
0.8218	Intermediate Similarity	NPC472815
0.8211	Intermediate Similarity	NPC473647
0.8211	Intermediate Similarity	NPC82876
0.8208	Intermediate Similarity	NPC470063
0.82	Intermediate Similarity	NPC38855
0.819	Intermediate Similarity	NPC103491
0.8182	Intermediate Similarity	NPC72260
0.8182	Intermediate Similarity	NPC475556
0.8182	Intermediate Similarity	NPC51499
0.8182	Intermediate Similarity	NPC475136
0.8182	Intermediate Similarity	NPC474466
0.8182	Intermediate Similarity	NPC475629
0.8173	Intermediate Similarity	NPC304276
0.8173	Intermediate Similarity	NPC88701
0.8173	Intermediate Similarity	NPC137462
0.8173	Intermediate Similarity	NPC275060
0.8163	Intermediate Similarity	NPC276110
0.8163	Intermediate Similarity	NPC472441
0.8152	Intermediate Similarity	NPC311070
0.8148	Intermediate Similarity	NPC469794
0.8148	Intermediate Similarity	NPC72772
0.8144	Intermediate Similarity	NPC476304
0.8144	Intermediate Similarity	NPC38232
0.8144	Intermediate Similarity	NPC7349
0.8137	Intermediate Similarity	NPC297617
0.8137	Intermediate Similarity	NPC281378
0.8125	Intermediate Similarity	NPC221111
0.8125	Intermediate Similarity	NPC280149
0.8119	Intermediate Similarity	NPC475617
0.8108	Intermediate Similarity	NPC173555
0.8108	Intermediate Similarity	NPC475590
0.8108	Intermediate Similarity	NPC474908
0.8108	Intermediate Similarity	NPC314535
0.8108	Intermediate Similarity	NPC475419
0.8108	Intermediate Similarity	NPC40749
0.8108	Intermediate Similarity	NPC475219
0.8108	Intermediate Similarity	NPC120390
0.8108	Intermediate Similarity	NPC231518
0.81	Intermediate Similarity	NPC325229
0.81	Intermediate Similarity	NPC275086
0.8085	Intermediate Similarity	NPC474970
0.8085	Intermediate Similarity	NPC475069
0.8085	Intermediate Similarity	NPC175145
0.8081	Intermediate Similarity	NPC473153
0.8073	Intermediate Similarity	NPC185287
0.8061	Intermediate Similarity	NPC476186
0.8041	Intermediate Similarity	NPC177641
0.8041	Intermediate Similarity	NPC472811
0.8041	Intermediate Similarity	NPC74296
0.8041	Intermediate Similarity	NPC110923
0.8037	Intermediate Similarity	NPC44537
0.8036	Intermediate Similarity	NPC74259
0.8036	Intermediate Similarity	NPC193893
0.8036	Intermediate Similarity	NPC115349
0.8036	Intermediate Similarity	NPC474423
0.8036	Intermediate Similarity	NPC264336
0.8021	Intermediate Similarity	NPC472240
0.8021	Intermediate Similarity	NPC262858
0.802	Intermediate Similarity	NPC474190
0.802	Intermediate Similarity	NPC208358
0.802	Intermediate Similarity	NPC117685
0.8019	Intermediate Similarity	NPC12795
0.8019	Intermediate Similarity	NPC179642
0.8019	Intermediate Similarity	NPC16270
0.8	Intermediate Similarity	NPC218093
0.8	Intermediate Similarity	NPC475033
0.8	Intermediate Similarity	NPC473891
0.8	Intermediate Similarity	NPC166857
0.8	Intermediate Similarity	NPC475032
0.7965	Intermediate Similarity	NPC308262
0.7965	Intermediate Similarity	NPC208193
0.7965	Intermediate Similarity	NPC27363
0.7965	Intermediate Similarity	NPC117445
0.7963	Intermediate Similarity	NPC171126
0.7961	Intermediate Similarity	NPC474124
0.7961	Intermediate Similarity	NPC45897
0.7961	Intermediate Similarity	NPC473523
0.7959	Intermediate Similarity	NPC472812
0.7959	Intermediate Similarity	NPC152778
0.7959	Intermediate Similarity	NPC307776
0.7959	Intermediate Similarity	NPC139692
0.7959	Intermediate Similarity	NPC205034
0.7959	Intermediate Similarity	NPC162615
0.7959	Intermediate Similarity	NPC472303
0.7957	Intermediate Similarity	NPC23748
0.7957	Intermediate Similarity	NPC470558
0.7957	Intermediate Similarity	NPC476927
0.7944	Intermediate Similarity	NPC183603
0.7944	Intermediate Similarity	NPC470076
0.7941	Intermediate Similarity	NPC155974
0.7938	Intermediate Similarity	NPC310479
0.7938	Intermediate Similarity	NPC182136
0.7928	Intermediate Similarity	NPC81222
0.7928	Intermediate Similarity	NPC278681
0.7928	Intermediate Similarity	NPC291820
0.7928	Intermediate Similarity	NPC153085
0.7928	Intermediate Similarity	NPC268326
0.7921	Intermediate Similarity	NPC278673
0.7921	Intermediate Similarity	NPC92275
0.7917	Intermediate Similarity	NPC93411
0.7917	Intermediate Similarity	NPC472809
0.7917	Intermediate Similarity	NPC472810

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 NPC231751 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1392
0.2-0.3	4007
0.3-0.4	2540
0.4-0.5	567
0.5-0.6	195
0.6-0.7	194
0.7-0.8	89
0.8-0.85	11
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8469	Intermediate Similarity	NPD7638	Approved
0.8384	Intermediate Similarity	NPD7639	Approved
0.8384	Intermediate Similarity	NPD7640	Approved
0.8333	Intermediate Similarity	NPD7327	Approved
0.8333	Intermediate Similarity	NPD7328	Approved
0.8257	Intermediate Similarity	NPD7516	Approved
0.8182	Intermediate Similarity	NPD8377	Approved
0.8182	Intermediate Similarity	NPD8294	Approved
0.8108	Intermediate Similarity	NPD8378	Approved
0.8108	Intermediate Similarity	NPD8380	Approved
0.8108	Intermediate Similarity	NPD8296	Approved
0.8108	Intermediate Similarity	NPD8379	Approved
0.8108	Intermediate Similarity	NPD8033	Approved
0.8108	Intermediate Similarity	NPD8335	Approved
0.8021	Intermediate Similarity	NPD6051	Approved
0.7826	Intermediate Similarity	NPD7507	Approved
0.7745	Intermediate Similarity	NPD4225	Approved
0.7692	Intermediate Similarity	NPD7632	Discontinued
0.7664	Intermediate Similarity	NPD7320	Approved
0.7647	Intermediate Similarity	NPD6083	Phase 2
0.7647	Intermediate Similarity	NPD6084	Phase 2
0.7642	Intermediate Similarity	NPD6675	Approved
0.7642	Intermediate Similarity	NPD5739	Approved
0.7642	Intermediate Similarity	NPD6402	Approved
0.7642	Intermediate Similarity	NPD7128	Approved
0.7634	Intermediate Similarity	NPD7525	Registered
0.7627	Intermediate Similarity	NPD7319	Approved
0.7589	Intermediate Similarity	NPD7115	Discovery
0.757	Intermediate Similarity	NPD5697	Approved
0.757	Intermediate Similarity	NPD5701	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD5693	Phase 1
0.75	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD6881	Approved
0.7478	Intermediate Similarity	NPD7503	Approved
0.7451	Intermediate Similarity	NPD5695	Phase 3
0.7431	Intermediate Similarity	NPD6013	Approved
0.7431	Intermediate Similarity	NPD6012	Approved
0.7431	Intermediate Similarity	NPD6014	Approved
0.7431	Intermediate Similarity	NPD6373	Approved
0.7431	Intermediate Similarity	NPD6372	Approved
0.7426	Intermediate Similarity	NPD4202	Approved
0.7404	Intermediate Similarity	NPD5696	Approved
0.7391	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD8297	Approved
0.7374	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6903	Approved
0.7364	Intermediate Similarity	NPD7102	Approved
0.7364	Intermediate Similarity	NPD7290	Approved
0.7364	Intermediate Similarity	NPD6883	Approved
0.7347	Intermediate Similarity	NPD5330	Approved
0.7347	Intermediate Similarity	NPD7146	Approved
0.7347	Intermediate Similarity	NPD7521	Approved
0.7347	Intermediate Similarity	NPD7334	Approved
0.7347	Intermediate Similarity	NPD6409	Approved
0.7347	Intermediate Similarity	NPD6684	Approved
0.734	Intermediate Similarity	NPD4195	Approved
0.7321	Intermediate Similarity	NPD4632	Approved
0.732	Intermediate Similarity	NPD3665	Phase 1
0.732	Intermediate Similarity	NPD3666	Approved
0.732	Intermediate Similarity	NPD3133	Approved
0.7308	Intermediate Similarity	NPD4755	Approved
0.73	Intermediate Similarity	NPD4753	Phase 2
0.7297	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6649	Approved
0.7297	Intermediate Similarity	NPD8130	Phase 1
0.7297	Intermediate Similarity	NPD6847	Approved
0.7297	Intermediate Similarity	NPD6869	Approved
0.7297	Intermediate Similarity	NPD6617	Approved
0.7297	Intermediate Similarity	NPD6650	Approved
0.7292	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6399	Phase 3
0.7232	Intermediate Similarity	NPD6882	Approved
0.7196	Intermediate Similarity	NPD5211	Phase 2
0.7184	Intermediate Similarity	NPD7748	Approved
0.7182	Intermediate Similarity	NPD6686	Approved
0.7172	Intermediate Similarity	NPD3618	Phase 1
0.717	Intermediate Similarity	NPD5286	Approved
0.717	Intermediate Similarity	NPD4696	Approved
0.717	Intermediate Similarity	NPD4700	Approved
0.717	Intermediate Similarity	NPD5285	Approved
0.7157	Intermediate Similarity	NPD7515	Phase 2
0.7156	Intermediate Similarity	NPD6008	Approved
0.7129	Intermediate Similarity	NPD6904	Approved
0.7129	Intermediate Similarity	NPD6673	Approved
0.7129	Intermediate Similarity	NPD5328	Approved
0.7129	Intermediate Similarity	NPD6080	Approved
0.7113	Intermediate Similarity	NPD4221	Approved
0.7113	Intermediate Similarity	NPD4223	Phase 3
0.7103	Intermediate Similarity	NPD5223	Approved
0.7097	Intermediate Similarity	NPD7339	Approved
0.7097	Intermediate Similarity	NPD6942	Approved
0.7094	Intermediate Similarity	NPD6319	Approved
0.708	Intermediate Similarity	NPD6053	Discontinued
0.7071	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5141	Approved
0.7043	Intermediate Similarity	NPD6274	Approved
0.7037	Intermediate Similarity	NPD5224	Approved
0.7037	Intermediate Similarity	NPD5225	Approved
0.7037	Intermediate Similarity	NPD5226	Approved
0.7037	Intermediate Similarity	NPD4633	Approved
0.703	Intermediate Similarity	NPD5737	Approved
0.703	Intermediate Similarity	NPD6672	Approved
0.703	Intermediate Similarity	NPD5208	Approved
0.7021	Intermediate Similarity	NPD6933	Approved
0.7019	Intermediate Similarity	NPD6001	Approved
0.699	Remote Similarity	NPD5281	Approved
0.699	Remote Similarity	NPD8034	Phase 2
0.699	Remote Similarity	NPD8035	Phase 2
0.699	Remote Similarity	NPD5284	Approved
0.699	Remote Similarity	NPD6079	Approved
0.6983	Remote Similarity	NPD6009	Approved
0.6983	Remote Similarity	NPD6317	Approved
0.6981	Remote Similarity	NPD7902	Approved
0.6972	Remote Similarity	NPD4754	Approved
0.6972	Remote Similarity	NPD5174	Approved
0.6972	Remote Similarity	NPD5175	Approved
0.697	Remote Similarity	NPD4197	Approved
0.697	Remote Similarity	NPD4786	Approved
0.6957	Remote Similarity	NPD4243	Approved
0.6952	Remote Similarity	NPD5210	Approved
0.6952	Remote Similarity	NPD4629	Approved
0.6944	Remote Similarity	NPD4159	Approved
0.6939	Remote Similarity	NPD3667	Approved
0.6937	Remote Similarity	NPD6412	Phase 2
0.6931	Remote Similarity	NPD7524	Approved
0.6923	Remote Similarity	NPD6314	Approved
0.6923	Remote Similarity	NPD6335	Approved
0.6923	Remote Similarity	NPD6313	Approved
0.6907	Remote Similarity	NPD4748	Discontinued
0.6903	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4634	Approved
0.69	Remote Similarity	NPD5329	Approved
0.6893	Remote Similarity	NPD5207	Approved
0.6893	Remote Similarity	NPD5692	Phase 3
0.6891	Remote Similarity	NPD5983	Phase 2
0.6891	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5222	Approved
0.6887	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4697	Phase 3
0.6887	Remote Similarity	NPD5221	Approved
0.687	Remote Similarity	NPD8133	Approved
0.6869	Remote Similarity	NPD4788	Approved
0.6869	Remote Similarity	NPD6695	Phase 3
0.6864	Remote Similarity	NPD7100	Approved
0.6864	Remote Similarity	NPD7101	Approved
0.686	Remote Similarity	NPD7492	Approved
0.6847	Remote Similarity	NPD4768	Approved
0.6847	Remote Similarity	NPD4767	Approved
0.6832	Remote Similarity	NPD4689	Approved
0.6832	Remote Similarity	NPD4693	Phase 3
0.6832	Remote Similarity	NPD6098	Approved
0.6832	Remote Similarity	NPD4138	Approved
0.6832	Remote Similarity	NPD4688	Approved
0.6832	Remote Similarity	NPD5205	Approved
0.6832	Remote Similarity	NPD4690	Approved
0.6829	Remote Similarity	NPD7736	Approved
0.6827	Remote Similarity	NPD6050	Approved
0.6827	Remote Similarity	NPD7637	Suspended
0.6827	Remote Similarity	NPD5694	Approved
0.6822	Remote Similarity	NPD5173	Approved
0.6809	Remote Similarity	NPD4785	Approved
0.6809	Remote Similarity	NPD4784	Approved
0.6809	Remote Similarity	NPD6926	Approved
0.6809	Remote Similarity	NPD6924	Approved
0.6807	Remote Similarity	NPD6059	Approved
0.6807	Remote Similarity	NPD6054	Approved
0.6804	Remote Similarity	NPD7645	Phase 2
0.6803	Remote Similarity	NPD6616	Approved
0.68	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5344	Discontinued
0.6777	Remote Similarity	NPD7604	Phase 2
0.675	Remote Similarity	NPD6015	Approved
0.675	Remote Similarity	NPD6016	Approved
0.675	Remote Similarity	NPD6909	Approved
0.675	Remote Similarity	NPD6908	Approved
0.6748	Remote Similarity	NPD8293	Discontinued
0.6748	Remote Similarity	NPD7078	Approved
0.6737	Remote Similarity	NPD4190	Phase 3
0.6737	Remote Similarity	NPD5275	Approved
0.6731	Remote Similarity	NPD5785	Approved
0.6726	Remote Similarity	NPD4730	Approved
0.6726	Remote Similarity	NPD4729	Approved
0.6726	Remote Similarity	NPD5128	Approved
0.6716	Remote Similarity	NPD7625	Phase 1
0.67	Remote Similarity	NPD5362	Discontinued
0.6698	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7900	Approved
0.6694	Remote Similarity	NPD5988	Approved
0.6694	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD4694	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