NPASS Compound

Structure

NPC475894 OpenBabel07101718292D 34 38 0 0 1 0 0 0 0 0999 V2000 -3.2372 5.2985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5244 4.1396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.8660 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 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8990 3.8122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8771 3.6043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2298 3.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5462 4.3475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 2.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 1 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 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4899 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 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 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2989 2.3968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4899 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 17 2 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 30 1 0 0 0 0 18 10 1 6 0 0 0 18 24 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 30 1 0 0 0 0 21 25 1 0 0 0 0 21 31 1 6 0 0 0 22 16 1 6 0 0 0 22 24 1 0 0 0 0 22 34 1 0 0 0 0 23 27 1 0 0 0 0 23 32 2 0 0 0 0 24 29 1 1 0 0 0 25 27 1 0 0 0 0 25 28 1 6 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.32
Volume:	509.269
LogP:	6.561
LogD:	4.477
LogS:	-6.729
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	5.215
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.089
MDCK Permeability:	2.294843397976365e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.558
30% Bioavailability (F30%):	0.878

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.347
Plasma Protein Binding (PPB):	87.26294708251953%
Volume Distribution (VD):	1.853
Pgp-substrate:	4.989246845245361%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.342
CYP2C19-inhibitor:	0.255
CYP2C19-substrate:	0.918
CYP2C9-inhibitor:	0.271
CYP2C9-substrate:	0.235
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.842
CYP3A4-substrate:	0.74

ADMET: Excretion

Clearance (CL):	12.694
Half-life (T1/2):	0.06

ADMET: Toxicity

hERG Blockers:	0.131
Human Hepatotoxicity (H-HT):	0.344
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.923
Maximum Recommended Daily Dose:	0.714
Skin Sensitization:	0.132
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC475894

Natural Product ID:	NPC475894
*Common Name:**	WBKKLEFJYBTBOA-GECUDYIRSA-N
IUPAC Name:	n.a.
Synonyms:	6Beta-Hydroxykulactone
Standard InCHIKey:	WBKKLEFJYBTBOA-GECUDYIRSA-N
Standard InCHI:	InChI=1S/C30H44O4/c1-17(2)9-8-10-18-24-22(34-26(18)33)16-30(7)20-15-21(31)25-27(3,4)23(32)12-13-28(25,5)19(20)11-14-29(24,30)6/h9,15,18-19,21-22,24-25,31H,8,10-14,16H2,1-7H3/t18-,19+,21-,22+,24-,25+,28-,29+,30-/m1/s1
SMILES:	CC(=CCC[C@H]1C(=O)O[C@@H]2[C@@H]1[C@]1(C)CC[C@H]3C(=C[C@H]([C@@H]4[C@]3(C)CCC(=O)C4(C)C)O)[C@]1(C2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518093
PubChem CID:	10004845
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO4571	Melia volkensii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10217705]
NPO4571	Melia volkensii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461654]
NPO4571	Melia volkensii	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	4.0	ug.mL-1	PMID[468735]

☑ 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 NPC475894 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	183
0.1-0.2	1044
0.2-0.3	4608
0.3-0.4	13799
0.4-0.5	8186
0.5-0.6	6016
0.6-0.7	6200
0.7-0.8	2383
0.8-0.85	241
0.85-0.9	32
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9355	High Similarity	NPC107243
0.9247	High Similarity	NPC322063
0.9231	High Similarity	NPC154101
0.9149	High Similarity	NPC57416
0.914	High Similarity	NPC469599
0.9111	High Similarity	NPC28227
0.9	High Similarity	NPC167877
0.8958	High Similarity	NPC218383
0.8925	High Similarity	NPC470224
0.8925	High Similarity	NPC243866
0.8889	High Similarity	NPC469994
0.8878	High Similarity	NPC140723
0.8866	High Similarity	NPC474327
0.8854	High Similarity	NPC153792
0.8854	High Similarity	NPC271387
0.8842	High Similarity	NPC155676
0.8817	High Similarity	NPC150383
0.8804	High Similarity	NPC54689
0.8804	High Similarity	NPC2983
0.8791	High Similarity	NPC317590
0.8778	High Similarity	NPC474218
0.8778	High Similarity	NPC470223
0.8778	High Similarity	NPC471224
0.8723	High Similarity	NPC66429
0.8723	High Similarity	NPC152897
0.8723	High Similarity	NPC470376
0.8723	High Similarity	NPC470375
0.871	High Similarity	NPC320026
0.8696	High Similarity	NPC294480
0.8687	High Similarity	NPC236390
0.8681	High Similarity	NPC322159
0.8673	High Similarity	NPC99411
0.8667	High Similarity	NPC165064
0.8667	High Similarity	NPC82902
0.8667	High Similarity	NPC100391
0.866	High Similarity	NPC48647
0.866	High Similarity	NPC235464
0.866	High Similarity	NPC197386
0.866	High Similarity	NPC166745
0.8602	High Similarity	NPC474570
0.8602	High Similarity	NPC155479
0.8602	High Similarity	NPC215029
0.8602	High Similarity	NPC476733
0.8602	High Similarity	NPC477943
0.86	High Similarity	NPC472227
0.86	High Similarity	NPC472228
0.8587	High Similarity	NPC312215
0.8587	High Similarity	NPC96496
0.8586	High Similarity	NPC204450
0.8586	High Similarity	NPC195290
0.8586	High Similarity	NPC136289
0.8571	High Similarity	NPC474083
0.8571	High Similarity	NPC476274
0.8542	High Similarity	NPC476174
0.8542	High Similarity	NPC69548
0.8542	High Similarity	NPC263347
0.8542	High Similarity	NPC184848
0.8526	High Similarity	NPC107674
0.8526	High Similarity	NPC141497
0.8526	High Similarity	NPC170220
0.8526	High Similarity	NPC472942
0.8526	High Similarity	NPC470254
0.8511	High Similarity	NPC171441
0.8511	High Similarity	NPC477147
0.8511	High Similarity	NPC471896
0.8511	High Similarity	NPC69622
0.8511	High Similarity	NPC477149
0.85	High Similarity	NPC476237
0.85	High Similarity	NPC36688
0.8495	Intermediate Similarity	NPC183546
0.8491	Intermediate Similarity	NPC49492
0.8491	Intermediate Similarity	NPC266728
0.8485	Intermediate Similarity	NPC476240
0.8485	Intermediate Similarity	NPC476223
0.8485	Intermediate Similarity	NPC81530
0.8485	Intermediate Similarity	NPC224720
0.8478	Intermediate Similarity	NPC212843
0.8478	Intermediate Similarity	NPC195640
0.8478	Intermediate Similarity	NPC470050
0.8478	Intermediate Similarity	NPC155011
0.8478	Intermediate Similarity	NPC470051
0.8469	Intermediate Similarity	NPC186810
0.8469	Intermediate Similarity	NPC477813
0.8462	Intermediate Similarity	NPC263974
0.8454	Intermediate Similarity	NPC472941
0.8454	Intermediate Similarity	NPC456
0.8454	Intermediate Similarity	NPC328371
0.8438	Intermediate Similarity	NPC184870
0.8438	Intermediate Similarity	NPC159410
0.8438	Intermediate Similarity	NPC471720
0.8438	Intermediate Similarity	NPC469406
0.8438	Intermediate Similarity	NPC7165
0.8431	Intermediate Similarity	NPC220974
0.8421	Intermediate Similarity	NPC86266
0.8421	Intermediate Similarity	NPC107690
0.8421	Intermediate Similarity	NPC297265
0.8421	Intermediate Similarity	NPC110657
0.8421	Intermediate Similarity	NPC23434
0.8421	Intermediate Similarity	NPC45269
0.8421	Intermediate Similarity	NPC473998
0.8421	Intermediate Similarity	NPC212301
0.8416	Intermediate Similarity	NPC255309
0.8404	Intermediate Similarity	NPC474704
0.8404	Intermediate Similarity	NPC281524
0.8404	Intermediate Similarity	NPC214387
0.8404	Intermediate Similarity	NPC309603
0.8404	Intermediate Similarity	NPC475921
0.8404	Intermediate Similarity	NPC473999
0.84	Intermediate Similarity	NPC56498
0.84	Intermediate Similarity	NPC473928
0.8387	Intermediate Similarity	NPC136948
0.8387	Intermediate Similarity	NPC474684
0.8387	Intermediate Similarity	NPC128644
0.8387	Intermediate Similarity	NPC142361
0.8384	Intermediate Similarity	NPC51370
0.8384	Intermediate Similarity	NPC287833
0.8384	Intermediate Similarity	NPC205899
0.8384	Intermediate Similarity	NPC477521
0.8384	Intermediate Similarity	NPC154072
0.837	Intermediate Similarity	NPC52628
0.837	Intermediate Similarity	NPC283733
0.837	Intermediate Similarity	NPC323765
0.8367	Intermediate Similarity	NPC253826
0.8367	Intermediate Similarity	NPC18319
0.8367	Intermediate Similarity	NPC121339
0.8351	Intermediate Similarity	NPC45324
0.8351	Intermediate Similarity	NPC318282
0.8351	Intermediate Similarity	NPC222845
0.8351	Intermediate Similarity	NPC173875
0.8351	Intermediate Similarity	NPC469995
0.8351	Intermediate Similarity	NPC472932
0.8351	Intermediate Similarity	NPC162001
0.8351	Intermediate Similarity	NPC174948
0.8333	Intermediate Similarity	NPC196528
0.8333	Intermediate Similarity	NPC206810
0.8333	Intermediate Similarity	NPC147066
0.8333	Intermediate Similarity	NPC96377
0.8317	Intermediate Similarity	NPC26478
0.8316	Intermediate Similarity	NPC111585
0.8316	Intermediate Similarity	NPC46281
0.8316	Intermediate Similarity	NPC123854
0.8316	Intermediate Similarity	NPC48010
0.8316	Intermediate Similarity	NPC469400
0.8316	Intermediate Similarity	NPC232202
0.8316	Intermediate Similarity	NPC148414
0.8316	Intermediate Similarity	NPC175628
0.8302	Intermediate Similarity	NPC962
0.8302	Intermediate Similarity	NPC250109
0.8298	Intermediate Similarity	NPC247406
0.8298	Intermediate Similarity	NPC328313
0.8298	Intermediate Similarity	NPC48866
0.8283	Intermediate Similarity	NPC478056
0.8283	Intermediate Similarity	NPC10364
0.828	Intermediate Similarity	NPC80590
0.828	Intermediate Similarity	NPC472505
0.828	Intermediate Similarity	NPC70661
0.8269	Intermediate Similarity	NPC474901
0.8269	Intermediate Similarity	NPC475941
0.8265	Intermediate Similarity	NPC3772
0.8265	Intermediate Similarity	NPC7124
0.8265	Intermediate Similarity	NPC235053
0.8265	Intermediate Similarity	NPC29152
0.8265	Intermediate Similarity	NPC42042
0.8261	Intermediate Similarity	NPC476038
0.8261	Intermediate Similarity	NPC161423
0.8261	Intermediate Similarity	NPC221758
0.8261	Intermediate Similarity	NPC227064
0.8261	Intermediate Similarity	NPC194937
0.8261	Intermediate Similarity	NPC58841
0.8261	Intermediate Similarity	NPC321187
0.8261	Intermediate Similarity	NPC85774
0.8261	Intermediate Similarity	NPC329043
0.8261	Intermediate Similarity	NPC59453
0.8261	Intermediate Similarity	NPC214043
0.8252	Intermediate Similarity	NPC131665
0.8252	Intermediate Similarity	NPC255387
0.8252	Intermediate Similarity	NPC91034
0.8247	Intermediate Similarity	NPC49670
0.8247	Intermediate Similarity	NPC472224
0.8247	Intermediate Similarity	NPC8993
0.8247	Intermediate Similarity	NPC292793
0.8247	Intermediate Similarity	NPC472223
0.8242	Intermediate Similarity	NPC170985
0.8242	Intermediate Similarity	NPC133391
0.8235	Intermediate Similarity	NPC471293
0.8235	Intermediate Similarity	NPC235889
0.8229	Intermediate Similarity	NPC189520
0.8229	Intermediate Similarity	NPC475806
0.8229	Intermediate Similarity	NPC26888
0.8229	Intermediate Similarity	NPC470113
0.8229	Intermediate Similarity	NPC471747
0.8218	Intermediate Similarity	NPC293753
0.8218	Intermediate Similarity	NPC234892
0.8218	Intermediate Similarity	NPC87351
0.8218	Intermediate Similarity	NPC185530
0.8218	Intermediate Similarity	NPC22388
0.8218	Intermediate Similarity	NPC477915
0.8211	Intermediate Similarity	NPC472971
0.8211	Intermediate Similarity	NPC474889
0.8211	Intermediate Similarity	NPC76879

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 NPC475894 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1300
0.2-0.3	3936
0.3-0.4	2611
0.4-0.5	622
0.5-0.6	184
0.6-0.7	179
0.7-0.8	149
0.8-0.85	22
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8723	High Similarity	NPD6399	Phase 3
0.8557	High Similarity	NPD6083	Phase 2
0.8557	High Similarity	NPD6084	Phase 2
0.8495	Intermediate Similarity	NPD6903	Approved
0.8478	Intermediate Similarity	NPD5330	Approved
0.8478	Intermediate Similarity	NPD6409	Approved
0.8478	Intermediate Similarity	NPD7521	Approved
0.8478	Intermediate Similarity	NPD6684	Approved
0.8478	Intermediate Similarity	NPD7334	Approved
0.8478	Intermediate Similarity	NPD7146	Approved
0.8351	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8283	Intermediate Similarity	NPD5696	Approved
0.8261	Intermediate Similarity	NPD3133	Approved
0.8261	Intermediate Similarity	NPD4786	Approved
0.8261	Intermediate Similarity	NPD3665	Phase 1
0.8261	Intermediate Similarity	NPD3666	Approved
0.8173	Intermediate Similarity	NPD7320	Approved
0.8163	Intermediate Similarity	NPD5695	Phase 3
0.8155	Intermediate Similarity	NPD6675	Approved
0.8155	Intermediate Similarity	NPD7128	Approved
0.8155	Intermediate Similarity	NPD6402	Approved
0.8155	Intermediate Similarity	NPD5739	Approved
0.8105	Intermediate Similarity	NPD6672	Approved
0.8105	Intermediate Similarity	NPD5737	Approved
0.8095	Intermediate Similarity	NPD6372	Approved
0.8095	Intermediate Similarity	NPD6373	Approved
0.8085	Intermediate Similarity	NPD6098	Approved
0.8043	Intermediate Similarity	NPD3667	Approved
0.8021	Intermediate Similarity	NPD6673	Approved
0.8021	Intermediate Similarity	NPD6080	Approved
0.8021	Intermediate Similarity	NPD6904	Approved
0.8021	Intermediate Similarity	NPD4753	Phase 2
0.802	Intermediate Similarity	NPD7639	Approved
0.802	Intermediate Similarity	NPD7640	Approved
0.8	Intermediate Similarity	NPD6899	Approved
0.8	Intermediate Similarity	NPD6881	Approved
0.7957	Intermediate Similarity	NPD5362	Discontinued
0.7944	Intermediate Similarity	NPD6649	Approved
0.7944	Intermediate Similarity	NPD6650	Approved
0.7938	Intermediate Similarity	NPD5207	Approved
0.7921	Intermediate Similarity	NPD7638	Approved
0.7905	Intermediate Similarity	NPD5701	Approved
0.7905	Intermediate Similarity	NPD5697	Approved
0.7895	Intermediate Similarity	NPD3618	Phase 1
0.7879	Intermediate Similarity	NPD6001	Approved
0.7857	Intermediate Similarity	NPD5281	Approved
0.7857	Intermediate Similarity	NPD5284	Approved
0.7857	Intermediate Similarity	NPD5693	Phase 1
0.785	Intermediate Similarity	NPD7102	Approved
0.785	Intermediate Similarity	NPD6883	Approved
0.785	Intermediate Similarity	NPD7290	Approved
0.7849	Intermediate Similarity	NPD4221	Approved
0.7849	Intermediate Similarity	NPD4223	Phase 3
0.7835	Intermediate Similarity	NPD5328	Approved
0.7835	Intermediate Similarity	NPD6051	Approved
0.783	Intermediate Similarity	NPD6011	Approved
0.781	Intermediate Similarity	NPD6008	Approved
0.7802	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD4629	Approved
0.78	Intermediate Similarity	NPD5210	Approved
0.7789	Intermediate Similarity	NPD5329	Approved
0.7778	Intermediate Similarity	NPD6847	Approved
0.7778	Intermediate Similarity	NPD8130	Phase 1
0.7778	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6869	Approved
0.7778	Intermediate Similarity	NPD6617	Approved
0.7778	Intermediate Similarity	NPD4202	Approved
0.7757	Intermediate Similarity	NPD6014	Approved
0.7757	Intermediate Similarity	NPD6012	Approved
0.7757	Intermediate Similarity	NPD6013	Approved
0.7748	Intermediate Similarity	NPD7115	Discovery
0.7732	Intermediate Similarity	NPD5208	Approved
0.7706	Intermediate Similarity	NPD8297	Approved
0.7706	Intermediate Similarity	NPD6882	Approved
0.77	Intermediate Similarity	NPD7748	Approved
0.7692	Intermediate Similarity	NPD5211	Phase 2
0.7684	Intermediate Similarity	NPD4197	Approved
0.7677	Intermediate Similarity	NPD8035	Phase 2
0.7677	Intermediate Similarity	NPD6050	Approved
0.7677	Intermediate Similarity	NPD8034	Phase 2
0.7677	Intermediate Similarity	NPD6079	Approved
0.7677	Intermediate Similarity	NPD7515	Phase 2
0.766	Intermediate Similarity	NPD4270	Approved
0.766	Intermediate Similarity	NPD4269	Approved
0.7647	Intermediate Similarity	NPD7902	Approved
0.7647	Intermediate Similarity	NPD4755	Approved
0.7619	Intermediate Similarity	NPD6052	Approved
0.7604	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD4788	Approved
0.7576	Intermediate Similarity	NPD5692	Phase 3
0.7576	Intermediate Similarity	NPD5785	Approved
0.757	Intermediate Similarity	NPD6412	Phase 2
0.7549	Intermediate Similarity	NPD4697	Phase 3
0.7547	Intermediate Similarity	NPD5141	Approved
0.7526	Intermediate Similarity	NPD5786	Approved
0.7526	Intermediate Similarity	NPD5205	Approved
0.7526	Intermediate Similarity	NPD4689	Approved
0.7526	Intermediate Similarity	NPD4688	Approved
0.7526	Intermediate Similarity	NPD4693	Phase 3
0.7526	Intermediate Similarity	NPD4138	Approved
0.7526	Intermediate Similarity	NPD5279	Phase 3
0.7526	Intermediate Similarity	NPD4690	Approved
0.75	Intermediate Similarity	NPD5286	Approved
0.75	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD3668	Phase 3
0.75	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD5285	Approved
0.75	Intermediate Similarity	NPD7637	Suspended
0.75	Intermediate Similarity	NPD5694	Approved
0.7478	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4252	Approved
0.7429	Intermediate Similarity	NPD5223	Approved
0.7423	Intermediate Similarity	NPD5363	Approved
0.7423	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5332	Approved
0.7396	Intermediate Similarity	NPD5331	Approved
0.7391	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6053	Discontinued
0.7379	Intermediate Similarity	NPD5221	Approved
0.7379	Intermediate Similarity	NPD5222	Approved
0.7379	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6335	Approved
0.7368	Intermediate Similarity	NPD5369	Approved
0.7368	Intermediate Similarity	NPD4790	Discontinued
0.7358	Intermediate Similarity	NPD5224	Approved
0.7358	Intermediate Similarity	NPD7632	Discontinued
0.7358	Intermediate Similarity	NPD5225	Approved
0.7358	Intermediate Similarity	NPD5226	Approved
0.7358	Intermediate Similarity	NPD4633	Approved
0.7353	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7900	Approved
0.7347	Intermediate Similarity	NPD5280	Approved
0.7347	Intermediate Similarity	NPD5690	Phase 2
0.7347	Intermediate Similarity	NPD4694	Approved
0.7347	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6274	Approved
0.7321	Intermediate Similarity	NPD4632	Approved
0.7308	Intermediate Similarity	NPD5173	Approved
0.7304	Intermediate Similarity	NPD7101	Approved
0.7304	Intermediate Similarity	NPD7100	Approved
0.7292	Intermediate Similarity	NPD6435	Approved
0.7292	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4754	Approved
0.729	Intermediate Similarity	NPD5174	Approved
0.729	Intermediate Similarity	NPD5175	Approved
0.7288	Intermediate Similarity	NPD7492	Approved
0.7283	Intermediate Similarity	NPD7339	Approved
0.7283	Intermediate Similarity	NPD6942	Approved
0.7281	Intermediate Similarity	NPD6317	Approved
0.7273	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD1694	Approved
0.7241	Intermediate Similarity	NPD6054	Approved
0.7241	Intermediate Similarity	NPD6059	Approved
0.7238	Intermediate Similarity	NPD4225	Approved
0.7227	Intermediate Similarity	NPD6616	Approved
0.7217	Intermediate Similarity	NPD6314	Approved
0.7217	Intermediate Similarity	NPD6313	Approved
0.7216	Intermediate Similarity	NPD7154	Phase 3
0.7193	Intermediate Similarity	NPD6868	Approved
0.7188	Intermediate Similarity	NPD4692	Approved
0.7188	Intermediate Similarity	NPD4139	Approved
0.7179	Intermediate Similarity	NPD6908	Approved
0.7179	Intermediate Similarity	NPD6909	Approved
0.7172	Intermediate Similarity	NPD4623	Approved
0.7172	Intermediate Similarity	NPD4519	Discontinued
0.7167	Intermediate Similarity	NPD8293	Discontinued
0.7167	Intermediate Similarity	NPD7078	Approved
0.7158	Intermediate Similarity	NPD4195	Approved
0.7157	Intermediate Similarity	NPD6411	Approved
0.7156	Intermediate Similarity	NPD4767	Approved
0.7156	Intermediate Similarity	NPD4768	Approved
0.7143	Intermediate Similarity	NPD5777	Approved
0.7143	Intermediate Similarity	NPD4243	Approved
0.713	Intermediate Similarity	NPD6009	Approved
0.7119	Intermediate Similarity	NPD6370	Approved
0.7115	Intermediate Similarity	NPD5654	Approved
0.7107	Intermediate Similarity	NPD7736	Approved
0.71	Intermediate Similarity	NPD4250	Approved
0.71	Intermediate Similarity	NPD4251	Approved
0.7097	Intermediate Similarity	NPD3702	Approved
0.7094	Intermediate Similarity	NPD6319	Approved
0.7091	Intermediate Similarity	NPD6614	Approved
0.7087	Intermediate Similarity	NPD5779	Approved
0.7087	Intermediate Similarity	NPD5778	Approved
0.7083	Intermediate Similarity	NPD7525	Registered
0.7083	Intermediate Similarity	NPD4822	Approved
0.7083	Intermediate Similarity	NPD4821	Approved
0.7083	Intermediate Similarity	NPD4819	Approved
0.7083	Intermediate Similarity	NPD7507	Approved
0.7083	Intermediate Similarity	NPD5368	Approved
0.7083	Intermediate Similarity	NPD4820	Approved
0.7059	Intermediate Similarity	NPD7604	Phase 2
0.7053	Intermediate Similarity	NPD4268	Approved
0.7053	Intermediate Similarity	NPD4271	Approved
0.7053	Intermediate Similarity	NPD3617	Approved
0.7041	Intermediate Similarity	NPD6695	Phase 3
0.7034	Intermediate Similarity	NPD6016	Approved
0.7034	Intermediate Similarity	NPD5983	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