NPASS Compound

Structure

CID233997 OpenBabel06191716032D 34 36 0 0 1 0 0 0 0 0999 V2000 -5.2105 2.7340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3445 4.2340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3356 -2.8981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7464 2.7340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0765 0.2340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0765 -2.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5855 0.9731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 -2.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9848 -1.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8508 0.6736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4784 2.7340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 -0.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3445 3.2340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 -2.0321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7464 1.7340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0765 1.2340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 -3.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4784 -0.2660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3445 0.2340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4784 1.7340 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6428 -0.7660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4784 -1.2660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3445 1.2340 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3445 -1.7660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9848 0.1736 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8804 1.2340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9425 1.7340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 -4.2660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 -1.2660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6124 1.2340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 1.7340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3445 -2.7660 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 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 11 26 1 0 0 0 0 12 14 2 0 0 0 0 13 20 2 0 0 0 0 13 30 1 0 0 0 0 16 27 2 0 0 0 0 16 31 1 0 0 0 0 17 28 2 0 0 0 0 17 32 1 0 0 0 0 18 29 2 0 0 0 0 18 33 1 0 0 0 0 19 10 1 1 0 0 0 19 20 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 12 1 6 0 0 0 21 24 1 0 0 0 0 21 31 1 0 0 0 0 22 26 1 1 0 0 0 22 34 1 0 0 0 0 23 15 1 6 0 0 0 23 25 1 0 0 0 0 24 32 1 1 0 0 0 25 30 1 0 0 0 0 25 33 1 1 0 0 0 26 7 1 1 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.24
Volume:	487.086
LogP:	3.416
LogD:	2.65
LogS:	-3.437
# Rotatable Bonds:	9
TPSA:	100.66
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.244
Synthetic Accessibility Score:	5.467
Fsp3:	0.654
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:	-4.99
MDCK Permeability:	0.00014575023669749498
Pgp-inhibitor:	0.934
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.072
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.398
Plasma Protein Binding (PPB):	63.1802864074707%
Volume Distribution (VD):	1.963
Pgp-substrate:	25.334007263183594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.146
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.652
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.477
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	2.833
Half-life (T1/2):	0.501

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.98
Drug-inuced Liver Injury (DILI):	0.847
AMES Toxicity:	0.986
Rat Oral Acute Toxicity:	0.339
Maximum Recommended Daily Dose:	0.137
Skin Sensitization:	0.3
Carcinogencity:	0.939
Eye Corrosion:	0.028
Eye Irritation:	0.027
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC233997

Natural Product ID:	NPC233997
*Common Name:**	LZOTVBPEWGLGQP-FOXVASFYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LZOTVBPEWGLGQP-FOXVASFYSA-N
Standard InCHI:	InChI=1S/C26H36O8/c1-14(2)12-21(31-16(4)27)24(32-17(5)28)20-13-30-25(33-18(6)29)23-15(3)8-9-22-26(7,34-22)11-10-19(20)23/h12-13,19,21-25H,3,8-11H2,1-2,4-7H3/t19-,21+,22+,23+,24-,25-,26+/m1/s1
SMILES:	CC(=C[C@@H]([C@@H](C1=CO[C@@H]([C@H]2C(=C)CC[C@H]3[C@](C)(CC[C@H]12)O3)OC(=O)C)OC(=O)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465147
PubChem CID:	11496604
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids

*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
NPO27036	Xenia blumi	Species	Xeniidae	Eukaryota	n.a.	Green Island, Taiwan	2002-MAY	PMID[16180809]
NPO27036	Xenia blumi	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23536	Alsophila spinulosa	Species	Cyatheaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18067	Muehlenbeckia platyclada	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26130	Cordia latifolia	Species	Cordiaceae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[477012]
NPT168	Cell Line	P388	Mus musculus	ED50	>	20.0	ug ml-1	PMID[477012]

☑ 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 NPC233997 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	247
0.1-0.2	2010
0.2-0.3	5848
0.3-0.4	16221
0.4-0.5	11629
0.5-0.6	5620
0.6-0.7	1070
0.7-0.8	37
0.8-0.85	9
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9059	High Similarity	NPC471480
0.9024	High Similarity	NPC475946
0.828	Intermediate Similarity	NPC241407
0.828	Intermediate Similarity	NPC291709
0.8211	Intermediate Similarity	NPC124181
0.8211	Intermediate Similarity	NPC90819
0.814	Intermediate Similarity	NPC474739
0.8105	Intermediate Similarity	NPC153559
0.8049	Intermediate Similarity	NPC477084
0.8021	Intermediate Similarity	NPC473307
0.7957	Intermediate Similarity	NPC66504
0.7835	Intermediate Similarity	NPC151093
0.7805	Intermediate Similarity	NPC269841
0.7755	Intermediate Similarity	NPC244878
0.7717	Intermediate Similarity	NPC74139
0.7677	Intermediate Similarity	NPC219038
0.7677	Intermediate Similarity	NPC98859
0.7677	Intermediate Similarity	NPC4637
0.7677	Intermediate Similarity	NPC20673
0.7674	Intermediate Similarity	NPC301525
0.7667	Intermediate Similarity	NPC475842
0.7634	Intermediate Similarity	NPC473151
0.76	Intermediate Similarity	NPC471599
0.7586	Intermediate Similarity	NPC84360
0.7558	Intermediate Similarity	NPC93213
0.7551	Intermediate Similarity	NPC86843
0.7527	Intermediate Similarity	NPC474765
0.75	Intermediate Similarity	NPC238090
0.75	Intermediate Similarity	NPC471494
0.75	Intermediate Similarity	NPC472195
0.75	Intermediate Similarity	NPC472196
0.7474	Intermediate Similarity	NPC202886
0.7473	Intermediate Similarity	NPC231601
0.7449	Intermediate Similarity	NPC284063
0.7423	Intermediate Similarity	NPC159698
0.7423	Intermediate Similarity	NPC274588
0.7423	Intermediate Similarity	NPC256368
0.7419	Intermediate Similarity	NPC311163
0.7368	Intermediate Similarity	NPC477748
0.7363	Intermediate Similarity	NPC10080
0.7363	Intermediate Similarity	NPC123908
0.7363	Intermediate Similarity	NPC475936
0.7347	Intermediate Similarity	NPC6765
0.7347	Intermediate Similarity	NPC93869
0.7333	Intermediate Similarity	NPC233332
0.7333	Intermediate Similarity	NPC190008
0.7327	Intermediate Similarity	NPC476228
0.732	Intermediate Similarity	NPC320089
0.7303	Intermediate Similarity	NPC264610
0.73	Intermediate Similarity	NPC279561
0.7292	Intermediate Similarity	NPC475748
0.7292	Intermediate Similarity	NPC3952
0.7283	Intermediate Similarity	NPC53867
0.7273	Intermediate Similarity	NPC170527
0.7273	Intermediate Similarity	NPC171598
0.7273	Intermediate Similarity	NPC288350
0.7273	Intermediate Similarity	NPC173329
0.7263	Intermediate Similarity	NPC248312
0.7253	Intermediate Similarity	NPC474894
0.7245	Intermediate Similarity	NPC88507
0.7245	Intermediate Similarity	NPC472198
0.7234	Intermediate Similarity	NPC204048
0.7234	Intermediate Similarity	NPC137253
0.7228	Intermediate Similarity	NPC130792
0.7222	Intermediate Similarity	NPC471537
0.7216	Intermediate Similarity	NPC472199
0.7216	Intermediate Similarity	NPC477749
0.7216	Intermediate Similarity	NPC472197
0.7204	Intermediate Similarity	NPC160517
0.7204	Intermediate Similarity	NPC78673
0.7204	Intermediate Similarity	NPC186155
0.72	Intermediate Similarity	NPC91197
0.72	Intermediate Similarity	NPC125551
0.72	Intermediate Similarity	NPC309503
0.72	Intermediate Similarity	NPC155319
0.72	Intermediate Similarity	NPC239547
0.72	Intermediate Similarity	NPC96597
0.7184	Intermediate Similarity	NPC197736
0.7184	Intermediate Similarity	NPC329834
0.7176	Intermediate Similarity	NPC329656
0.7172	Intermediate Similarity	NPC471362
0.7172	Intermediate Similarity	NPC107476
0.7172	Intermediate Similarity	NPC471372
0.7172	Intermediate Similarity	NPC472189
0.7158	Intermediate Similarity	NPC231889
0.7157	Intermediate Similarity	NPC280991
0.7143	Intermediate Similarity	NPC469802
0.7143	Intermediate Similarity	NPC61201
0.7129	Intermediate Similarity	NPC476800
0.7129	Intermediate Similarity	NPC318917
0.7129	Intermediate Similarity	NPC472186
0.7129	Intermediate Similarity	NPC471366
0.7128	Intermediate Similarity	NPC472442
0.7128	Intermediate Similarity	NPC474547
0.7126	Intermediate Similarity	NPC477085
0.7115	Intermediate Similarity	NPC307846
0.7115	Intermediate Similarity	NPC305157
0.7113	Intermediate Similarity	NPC177668
0.7111	Intermediate Similarity	NPC477089
0.7111	Intermediate Similarity	NPC474341
0.7111	Intermediate Similarity	NPC474005
0.71	Intermediate Similarity	NPC311166
0.71	Intermediate Similarity	NPC54731
0.71	Intermediate Similarity	NPC8954
0.71	Intermediate Similarity	NPC94905
0.7097	Intermediate Similarity	NPC49208
0.7097	Intermediate Similarity	NPC170286
0.7087	Intermediate Similarity	NPC13171
0.7087	Intermediate Similarity	NPC195510
0.7087	Intermediate Similarity	NPC201191
0.7071	Intermediate Similarity	NPC477722
0.7059	Intermediate Similarity	NPC476320
0.7059	Intermediate Similarity	NPC473545
0.7059	Intermediate Similarity	NPC476211
0.7059	Intermediate Similarity	NPC473204
0.7059	Intermediate Similarity	NPC472187
0.7059	Intermediate Similarity	NPC475053
0.7053	Intermediate Similarity	NPC61527
0.7053	Intermediate Similarity	NPC474045
0.7053	Intermediate Similarity	NPC47220
0.7053	Intermediate Similarity	NPC186332
0.7053	Intermediate Similarity	NPC261253
0.7048	Intermediate Similarity	NPC469401
0.7048	Intermediate Similarity	NPC239961
0.7033	Intermediate Similarity	NPC86971
0.7033	Intermediate Similarity	NPC139712
0.703	Intermediate Similarity	NPC472188
0.703	Intermediate Similarity	NPC113976
0.703	Intermediate Similarity	NPC473244
0.703	Intermediate Similarity	NPC471490
0.703	Intermediate Similarity	NPC198549
0.703	Intermediate Similarity	NPC98112
0.7021	Intermediate Similarity	NPC266718
0.7021	Intermediate Similarity	NPC474776
0.7011	Intermediate Similarity	NPC477087
0.7011	Intermediate Similarity	NPC477086
0.701	Intermediate Similarity	NPC64913
0.701	Intermediate Similarity	NPC246028
0.701	Intermediate Similarity	NPC133450
0.701	Intermediate Similarity	NPC293044
0.701	Intermediate Similarity	NPC242877
0.7009	Intermediate Similarity	NPC133625
0.7	Intermediate Similarity	NPC471492
0.7	Intermediate Similarity	NPC40049
0.699	Remote Similarity	NPC198992
0.699	Remote Similarity	NPC473332
0.699	Remote Similarity	NPC216911
0.699	Remote Similarity	NPC27474
0.699	Remote Similarity	NPC476230
0.6989	Remote Similarity	NPC103171
0.6979	Remote Similarity	NPC471055
0.6979	Remote Similarity	NPC316138
0.6979	Remote Similarity	NPC313658
0.6979	Remote Similarity	NPC471056
0.6977	Remote Similarity	NPC101622
0.697	Remote Similarity	NPC474835
0.6966	Remote Similarity	NPC475861
0.6961	Remote Similarity	NPC203627
0.6961	Remote Similarity	NPC312325
0.6952	Remote Similarity	NPC86095
0.6947	Remote Similarity	NPC477746
0.6947	Remote Similarity	NPC477747
0.6939	Remote Similarity	NPC327253
0.6939	Remote Similarity	NPC303451
0.6939	Remote Similarity	NPC6414
0.6931	Remote Similarity	NPC476315
0.6923	Remote Similarity	NPC222062
0.6923	Remote Similarity	NPC470972
0.6916	Remote Similarity	NPC135015
0.6916	Remote Similarity	NPC217921
0.6916	Remote Similarity	NPC128795
0.6916	Remote Similarity	NPC48548
0.6915	Remote Similarity	NPC127917
0.6915	Remote Similarity	NPC23748
0.6915	Remote Similarity	NPC472440
0.6915	Remote Similarity	NPC170377
0.6909	Remote Similarity	NPC287075
0.6907	Remote Similarity	NPC106332
0.6903	Remote Similarity	NPC219656
0.69	Remote Similarity	NPC281775
0.69	Remote Similarity	NPC178949
0.69	Remote Similarity	NPC96736
0.69	Remote Similarity	NPC140277
0.6897	Remote Similarity	NPC4299
0.6893	Remote Similarity	NPC13743
0.6893	Remote Similarity	NPC255677
0.6893	Remote Similarity	NPC22149
0.6893	Remote Similarity	NPC306344
0.6893	Remote Similarity	NPC98813
0.6889	Remote Similarity	NPC256720
0.6889	Remote Similarity	NPC469880
0.6889	Remote Similarity	NPC236228
0.6882	Remote Similarity	NPC475481
0.6882	Remote Similarity	NPC246621
0.6882	Remote Similarity	NPC79277
0.6882	Remote Similarity	NPC25554
0.6875	Remote Similarity	NPC102996
0.6875	Remote Similarity	NPC50637
0.6875	Remote Similarity	NPC214315
0.6869	Remote Similarity	NPC158061

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 NPC233997 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	2511
0.2-0.3	3785
0.3-0.4	2029
0.4-0.5	484
0.5-0.6	94
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7113	Intermediate Similarity	NPD6698	Approved
0.7113	Intermediate Similarity	NPD7838	Discovery
0.7113	Intermediate Similarity	NPD46	Approved
0.6961	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6648	Approved
0.6827	Remote Similarity	NPD5344	Discontinued
0.6759	Remote Similarity	NPD6686	Approved
0.6638	Remote Similarity	NPD7503	Approved
0.6598	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7328	Approved
0.6379	Remote Similarity	NPD7327	Approved
0.6356	Remote Similarity	NPD8513	Phase 3
0.6356	Remote Similarity	NPD8033	Approved
0.6337	Remote Similarity	NPD1695	Approved
0.6325	Remote Similarity	NPD7516	Approved
0.6275	Remote Similarity	NPD3168	Discontinued
0.6271	Remote Similarity	NPD8294	Approved
0.6271	Remote Similarity	NPD8377	Approved
0.6218	Remote Similarity	NPD8515	Approved
0.6218	Remote Similarity	NPD8516	Approved
0.6218	Remote Similarity	NPD8517	Approved
0.6218	Remote Similarity	NPD8296	Approved
0.6218	Remote Similarity	NPD8380	Approved
0.6218	Remote Similarity	NPD8335	Approved
0.6218	Remote Similarity	NPD8379	Approved
0.6218	Remote Similarity	NPD8378	Approved
0.6216	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7983	Approved
0.6176	Remote Similarity	NPD6051	Approved
0.6139	Remote Similarity	NPD4250	Approved
0.6139	Remote Similarity	NPD4251	Approved
0.6087	Remote Similarity	NPD6053	Discontinued
0.6061	Remote Similarity	NPD7154	Phase 3
0.6053	Remote Similarity	NPD6371	Approved
0.604	Remote Similarity	NPD4249	Approved
0.6019	Remote Similarity	NPD7638	Approved
0.6016	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD5778	Approved
0.5984	Remote Similarity	NPD7830	Approved
0.5984	Remote Similarity	NPD7642	Approved
0.5984	Remote Similarity	NPD7829	Approved
0.5981	Remote Similarity	NPD7839	Suspended
0.5963	Remote Similarity	NPD7639	Approved
0.5963	Remote Similarity	NPD7640	Approved
0.596	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD8133	Approved
0.5895	Remote Similarity	NPD8039	Approved
0.5887	Remote Similarity	NPD8451	Approved
0.5873	Remote Similarity	NPD7319	Approved
0.5872	Remote Similarity	NPD4225	Approved
0.5862	Remote Similarity	NPD1145	Discontinued
0.5843	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.584	Remote Similarity	NPD8448	Approved
0.5825	Remote Similarity	NPD7524	Approved
0.582	Remote Similarity	NPD8444	Approved
0.58	Remote Similarity	NPD5209	Approved
0.5789	Remote Similarity	NPD6412	Phase 2
0.5776	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD4821	Approved
0.5758	Remote Similarity	NPD4820	Approved
0.5758	Remote Similarity	NPD4819	Approved
0.5758	Remote Similarity	NPD4822	Approved
0.5758	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD7637	Suspended
0.575	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.575	Remote Similarity	NPD7115	Discovery
0.5743	Remote Similarity	NPD6695	Phase 3
0.5743	Remote Similarity	NPD5362	Discontinued
0.5743	Remote Similarity	NPD6110	Phase 1
0.5714	Remote Similarity	NPD8074	Phase 3
0.5714	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD8390	Approved
0.5703	Remote Similarity	NPD8392	Approved
0.5703	Remote Similarity	NPD8391	Approved
0.5702	Remote Similarity	NPD5357	Phase 1
0.569	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.569	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.568	Remote Similarity	NPD8342	Approved
0.568	Remote Similarity	NPD8299	Approved
0.568	Remote Similarity	NPD8340	Approved
0.568	Remote Similarity	NPD8341	Approved
0.5648	Remote Similarity	NPD5282	Discontinued
0.5635	Remote Similarity	NPD8273	Phase 1
0.5631	Remote Similarity	NPD1694	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