NPASS Compound

Structure

NPC475936 OpenBabel07101719132D 24 27 0 0 1 0 0 0 0 0999 V2000 -0.8119 -4.1829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9245 0.0835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9602 0.0835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5344 -0.9710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9496 -2.6091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1251 -3.0331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9496 -1.6448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1251 -2.0688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7847 -2.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4549 -1.2208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2900 -4.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3298 -3.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2900 -3.5152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4549 -3.0331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9602 -1.5867 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.3298 -0.9061 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6198 -3.5152 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6198 -4.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4424 -0.7516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6198 -0.7387 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2153 -4.9617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4549 -4.9617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9245 -1.5867 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 12 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 7 1 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 13 2 0 0 0 0 7 16 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 13 14 1 0 0 0 0 14 9 1 6 0 0 0 14 17 1 0 0 0 0 15 19 1 0 0 0 0 15 23 1 0 0 0 0 16 20 1 6 0 0 0 16 24 1 0 0 0 0 17 12 1 1 0 0 0 17 18 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 4 1 6 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	347.502
LogP:	4.133
LogD:	3.448
LogS:	-4.482
# Rotatable Bonds:	2
TPSA:	51.36
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.439
Synthetic Accessibility Score:	5.163
Fsp3:	0.75
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:	-4.774
MDCK Permeability:	2.7780337404692546e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	93.32428741455078%
Volume Distribution (VD):	1.571
Pgp-substrate:	2.843034267425537%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.395
CYP2C19-inhibitor:	0.287
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.322
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.264
CYP3A4-inhibitor:	0.741
CYP3A4-substrate:	0.56

ADMET: Excretion

Clearance (CL):	8.595
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.358
Drug-inuced Liver Injury (DILI):	0.325
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.713
Carcinogencity:	0.771
Eye Corrosion:	0.016
Eye Irritation:	0.058
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC475936

Natural Product ID:	NPC475936
*Common Name:**	HBFMHROJNZWLBE-SCWJKOTBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HBFMHROJNZWLBE-SCWJKOTBSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-12-5-7-16-20(4,24-16)10-9-14-13(11-22-18(21)17(12)14)6-8-15-19(2,3)23-15/h6,14-17H,1,5,7-11H2,2-4H3/b13-6-/t14-,15?,16+,17+,20+/m1/s1
SMILES:	CC1(C(O1)CC=C2COC(=O)C3C2CCC4(C(O4)CCC3=C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518878
PubChem CID:	11727307
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[12502332]
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562830]
NPO14298	Xenia umbellata	Species	Xeniidae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	11.6	ug ml-1	PMID[536445]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	7.77	ug ml-1	PMID[536445]
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.35	ug ml-1	PMID[536445]

☑ 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 NPC475936 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	229
0.1-0.2	1413
0.2-0.3	5908
0.3-0.4	16376
0.4-0.5	9941
0.5-0.6	6715
0.6-0.7	2014
0.7-0.8	85
0.8-0.85	7
0.85-0.9	5
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9367	High Similarity	NPC475842
0.9367	High Similarity	NPC53867
0.9221	High Similarity	NPC474341
0.9079	High Similarity	NPC475861
0.8706	High Similarity	NPC106040
0.8706	High Similarity	NPC115179
0.8675	High Similarity	NPC474369
0.8675	High Similarity	NPC474547
0.8571	High Similarity	NPC135703
0.8571	High Similarity	NPC116575
0.8471	Intermediate Similarity	NPC474765
0.8415	Intermediate Similarity	NPC79277
0.8415	Intermediate Similarity	NPC475481
0.8276	Intermediate Similarity	NPC212598
0.8193	Intermediate Similarity	NPC141810
0.8148	Intermediate Similarity	NPC107668
0.8118	Intermediate Similarity	NPC72464
0.8	Intermediate Similarity	NPC475989
0.7952	Intermediate Similarity	NPC617
0.7931	Intermediate Similarity	NPC234038
0.7907	Intermediate Similarity	NPC474776
0.7907	Intermediate Similarity	NPC196487
0.7907	Intermediate Similarity	NPC14575
0.7882	Intermediate Similarity	NPC35556
0.7872	Intermediate Similarity	NPC475053
0.7848	Intermediate Similarity	NPC475310
0.7841	Intermediate Similarity	NPC231889
0.7841	Intermediate Similarity	NPC475703
0.7826	Intermediate Similarity	NPC272050
0.7826	Intermediate Similarity	NPC107476
0.7805	Intermediate Similarity	NPC271070
0.7805	Intermediate Similarity	NPC110461
0.7805	Intermediate Similarity	NPC12740
0.7805	Intermediate Similarity	NPC61863
0.7802	Intermediate Similarity	NPC476049
0.7791	Intermediate Similarity	NPC222358
0.7791	Intermediate Similarity	NPC170377
0.7791	Intermediate Similarity	NPC272814
0.775	Intermediate Similarity	NPC477084
0.7727	Intermediate Similarity	NPC198314
0.7727	Intermediate Similarity	NPC261253
0.7727	Intermediate Similarity	NPC474045
0.7727	Intermediate Similarity	NPC50637
0.7711	Intermediate Similarity	NPC470240
0.7711	Intermediate Similarity	NPC476794
0.7701	Intermediate Similarity	NPC9868
0.7701	Intermediate Similarity	NPC70424
0.7701	Intermediate Similarity	NPC243618
0.7667	Intermediate Similarity	NPC166919
0.7647	Intermediate Similarity	NPC474510
0.7647	Intermediate Similarity	NPC233377
0.7647	Intermediate Similarity	NPC103634
0.7619	Intermediate Similarity	NPC128276
0.759	Intermediate Similarity	NPC474447
0.759	Intermediate Similarity	NPC235906
0.759	Intermediate Similarity	NPC301525
0.7586	Intermediate Similarity	NPC193198
0.7586	Intermediate Similarity	NPC474703
0.7582	Intermediate Similarity	NPC62815
0.7582	Intermediate Similarity	NPC475748
0.7582	Intermediate Similarity	NPC51653
0.7561	Intermediate Similarity	NPC476355
0.7561	Intermediate Similarity	NPC474551
0.7561	Intermediate Similarity	NPC140287
0.7558	Intermediate Similarity	NPC301477
0.7558	Intermediate Similarity	NPC325031
0.7558	Intermediate Similarity	NPC281949
0.7558	Intermediate Similarity	NPC471325
0.7558	Intermediate Similarity	NPC25684
0.7556	Intermediate Similarity	NPC475902
0.7531	Intermediate Similarity	NPC129665
0.7531	Intermediate Similarity	NPC163003
0.7529	Intermediate Similarity	NPC469617
0.7529	Intermediate Similarity	NPC178277
0.7528	Intermediate Similarity	NPC220478
0.7528	Intermediate Similarity	NPC122502
0.7528	Intermediate Similarity	NPC469676
0.7527	Intermediate Similarity	NPC38830
0.7527	Intermediate Similarity	NPC471147
0.75	Intermediate Similarity	NPC20713
0.75	Intermediate Similarity	NPC41780
0.75	Intermediate Similarity	NPC295799
0.75	Intermediate Similarity	NPC187568
0.75	Intermediate Similarity	NPC82297
0.75	Intermediate Similarity	NPC49420
0.75	Intermediate Similarity	NPC57744
0.75	Intermediate Similarity	NPC269841
0.75	Intermediate Similarity	NPC475972
0.75	Intermediate Similarity	NPC65603
0.7473	Intermediate Similarity	NPC151770
0.7473	Intermediate Similarity	NPC475971
0.7471	Intermediate Similarity	NPC471159
0.7471	Intermediate Similarity	NPC173609
0.7471	Intermediate Similarity	NPC89555
0.7471	Intermediate Similarity	NPC123880
0.747	Intermediate Similarity	NPC474419
0.747	Intermediate Similarity	NPC324762
0.747	Intermediate Similarity	NPC244166
0.7444	Intermediate Similarity	NPC74139
0.7442	Intermediate Similarity	NPC474739
0.7442	Intermediate Similarity	NPC47747
0.7439	Intermediate Similarity	NPC238425
0.7439	Intermediate Similarity	NPC472018
0.7439	Intermediate Similarity	NPC474543
0.7416	Intermediate Similarity	NPC78089
0.7416	Intermediate Similarity	NPC96621
0.7412	Intermediate Similarity	NPC63445
0.7412	Intermediate Similarity	NPC222210
0.7412	Intermediate Similarity	NPC474005
0.7412	Intermediate Similarity	NPC471220
0.7407	Intermediate Similarity	NPC69462
0.7407	Intermediate Similarity	NPC472955
0.7396	Intermediate Similarity	NPC208233
0.7391	Intermediate Similarity	NPC312042
0.7391	Intermediate Similarity	NPC329857
0.7391	Intermediate Similarity	NPC469718
0.7386	Intermediate Similarity	NPC475622
0.7386	Intermediate Similarity	NPC108045
0.7386	Intermediate Similarity	NPC170286
0.7381	Intermediate Similarity	NPC123360
0.7375	Intermediate Similarity	NPC276290
0.7363	Intermediate Similarity	NPC281516
0.7363	Intermediate Similarity	NPC233997
0.7363	Intermediate Similarity	NPC473151
0.7363	Intermediate Similarity	NPC477128
0.7356	Intermediate Similarity	NPC14203
0.7356	Intermediate Similarity	NPC229584
0.7356	Intermediate Similarity	NPC42470
0.7349	Intermediate Similarity	NPC474758
0.7349	Intermediate Similarity	NPC330016
0.734	Intermediate Similarity	NPC140543
0.734	Intermediate Similarity	NPC473316
0.734	Intermediate Similarity	NPC474035
0.734	Intermediate Similarity	NPC473330
0.734	Intermediate Similarity	NPC476267
0.734	Intermediate Similarity	NPC81386
0.7333	Intermediate Similarity	NPC107787
0.7333	Intermediate Similarity	NPC284902
0.7326	Intermediate Similarity	NPC182550
0.7326	Intermediate Similarity	NPC469620
0.7326	Intermediate Similarity	NPC469690
0.7326	Intermediate Similarity	NPC471740
0.7326	Intermediate Similarity	NPC89128
0.7312	Intermediate Similarity	NPC470373
0.7312	Intermediate Similarity	NPC470379
0.7312	Intermediate Similarity	NPC219874
0.7303	Intermediate Similarity	NPC470238
0.7303	Intermediate Similarity	NPC149869
0.7303	Intermediate Similarity	NPC159635
0.7303	Intermediate Similarity	NPC138647
0.7303	Intermediate Similarity	NPC474359
0.7294	Intermediate Similarity	NPC84360
0.7294	Intermediate Similarity	NPC97516
0.7294	Intermediate Similarity	NPC476028
0.7294	Intermediate Similarity	NPC476264
0.7294	Intermediate Similarity	NPC141789
0.7294	Intermediate Similarity	NPC171204
0.7294	Intermediate Similarity	NPC474760
0.7294	Intermediate Similarity	NPC476325
0.7292	Intermediate Similarity	NPC471140
0.7284	Intermediate Similarity	NPC199557
0.7284	Intermediate Similarity	NPC107130
0.7284	Intermediate Similarity	NPC101622
0.7283	Intermediate Similarity	NPC284561
0.7283	Intermediate Similarity	NPC83423
0.7273	Intermediate Similarity	NPC145963
0.7273	Intermediate Similarity	NPC85772
0.7273	Intermediate Similarity	NPC200513
0.7273	Intermediate Similarity	NPC474291
0.7263	Intermediate Similarity	NPC270013
0.7263	Intermediate Similarity	NPC474947
0.7263	Intermediate Similarity	NPC14961
0.7262	Intermediate Similarity	NPC138408
0.7262	Intermediate Similarity	NPC193351
0.7262	Intermediate Similarity	NPC226669
0.7262	Intermediate Similarity	NPC60718
0.7262	Intermediate Similarity	NPC155587
0.7253	Intermediate Similarity	NPC312561
0.7245	Intermediate Similarity	NPC264477
0.7245	Intermediate Similarity	NPC477511
0.7241	Intermediate Similarity	NPC475946
0.7241	Intermediate Similarity	NPC195424
0.7241	Intermediate Similarity	NPC276356
0.7234	Intermediate Similarity	NPC212486
0.7234	Intermediate Similarity	NPC125674
0.7234	Intermediate Similarity	NPC228451
0.7234	Intermediate Similarity	NPC475838
0.7229	Intermediate Similarity	NPC58956
0.7229	Intermediate Similarity	NPC167145
0.7229	Intermediate Similarity	NPC92909
0.7229	Intermediate Similarity	NPC295633
0.7229	Intermediate Similarity	NPC269206
0.7229	Intermediate Similarity	NPC107783
0.7222	Intermediate Similarity	NPC235792
0.7222	Intermediate Similarity	NPC197903
0.7222	Intermediate Similarity	NPC189311
0.7222	Intermediate Similarity	NPC319795
0.7222	Intermediate Similarity	NPC255307
0.7222	Intermediate Similarity	NPC261380
0.7222	Intermediate Similarity	NPC38468

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 NPC475936 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1851
0.2-0.3	4030
0.3-0.4	2158
0.4-0.5	669
0.5-0.6	216
0.6-0.7	26
0.7-0.8	2
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
0.7436	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6698	Approved
0.7391	Intermediate Similarity	NPD46	Approved
0.7273	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1695	Approved
0.7059	Intermediate Similarity	NPD8039	Approved
0.6915	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6101	Approved
0.6875	Remote Similarity	NPD5778	Approved
0.6875	Remote Similarity	NPD5779	Approved
0.6848	Remote Similarity	NPD1694	Approved
0.6813	Remote Similarity	NPD5362	Discontinued
0.6813	Remote Similarity	NPD7154	Phase 3
0.6771	Remote Similarity	NPD6411	Approved
0.6703	Remote Similarity	NPD5209	Approved
0.6634	Remote Similarity	NPD6648	Approved
0.6596	Remote Similarity	NPD6422	Discontinued
0.6596	Remote Similarity	NPD5786	Approved
0.6593	Remote Similarity	NPD5369	Approved
0.6569	Remote Similarity	NPD5344	Discontinued
0.6566	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4270	Approved
0.6522	Remote Similarity	NPD4269	Approved
0.6522	Remote Similarity	NPD6435	Approved
0.65	Remote Similarity	NPD7839	Suspended
0.6495	Remote Similarity	NPD7838	Discovery
0.6495	Remote Similarity	NPD5785	Approved
0.6489	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4820	Approved
0.6484	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4821	Approved
0.6484	Remote Similarity	NPD4819	Approved
0.6484	Remote Similarity	NPD4822	Approved
0.6444	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7983	Approved
0.6429	Remote Similarity	NPD5693	Phase 1
0.6421	Remote Similarity	NPD6684	Approved
0.6421	Remote Similarity	NPD7521	Approved
0.6421	Remote Similarity	NPD7334	Approved
0.6421	Remote Similarity	NPD6409	Approved
0.6421	Remote Similarity	NPD7146	Approved
0.6421	Remote Similarity	NPD5330	Approved
0.6415	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6051	Approved
0.6364	Remote Similarity	NPD6399	Phase 3
0.6354	Remote Similarity	NPD3573	Approved
0.6321	Remote Similarity	NPD6008	Approved
0.6316	Remote Similarity	NPD5363	Approved
0.6304	Remote Similarity	NPD4252	Approved
0.6304	Remote Similarity	NPD5368	Approved
0.6296	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6672	Approved
0.6289	Remote Similarity	NPD6903	Approved
0.6289	Remote Similarity	NPD5737	Approved
0.6289	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5331	Approved
0.6277	Remote Similarity	NPD5332	Approved
0.6273	Remote Similarity	NPD6053	Discontinued
0.6264	Remote Similarity	NPD4271	Approved
0.6264	Remote Similarity	NPD4268	Approved
0.6262	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6371	Approved
0.6239	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4790	Discontinued
0.6214	Remote Similarity	NPD7638	Approved
0.6214	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4225	Approved
0.6204	Remote Similarity	NPD6686	Approved
0.6195	Remote Similarity	NPD7115	Discovery
0.6182	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7640	Approved
0.6154	Remote Similarity	NPD7639	Approved
0.6139	Remote Similarity	NPD7900	Approved
0.6139	Remote Similarity	NPD5282	Discontinued
0.6139	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7748	Approved
0.6118	Remote Similarity	NPD7331	Phase 2
0.6082	Remote Similarity	NPD4249	Approved
0.6082	Remote Similarity	NPD6098	Approved
0.6078	Remote Similarity	NPD5695	Phase 3
0.6078	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6080	Approved
0.6061	Remote Similarity	NPD6904	Approved
0.6061	Remote Similarity	NPD6673	Approved
0.6042	Remote Similarity	NPD3668	Phase 3
0.602	Remote Similarity	NPD4251	Approved
0.602	Remote Similarity	NPD4250	Approved
0.6	Remote Similarity	NPD7341	Phase 2
0.6	Remote Similarity	NPD5692	Phase 3
0.6	Remote Similarity	NPD3667	Approved
0.598	Remote Similarity	NPD6001	Approved
0.5978	Remote Similarity	NPD4756	Discovery
0.5974	Remote Similarity	NPD6927	Phase 3
0.5962	Remote Similarity	NPD7902	Approved
0.5962	Remote Similarity	NPD6083	Phase 2
0.5962	Remote Similarity	NPD6084	Phase 2
0.596	Remote Similarity	NPD5208	Approved
0.5941	Remote Similarity	NPD6050	Approved
0.5941	Remote Similarity	NPD7515	Phase 2
0.5941	Remote Similarity	NPD7637	Suspended
0.5941	Remote Similarity	NPD5694	Approved
0.5905	Remote Similarity	NPD5696	Approved
0.5876	Remote Similarity	NPD4786	Approved
0.5876	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7128	Approved
0.5872	Remote Similarity	NPD6402	Approved
0.5872	Remote Similarity	NPD6675	Approved
0.5872	Remote Similarity	NPD5739	Approved
0.5865	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD8513	Phase 3
0.5847	Remote Similarity	NPD8517	Approved
0.5847	Remote Similarity	NPD8515	Approved
0.5847	Remote Similarity	NPD8516	Approved
0.5842	Remote Similarity	NPD5207	Approved
0.5842	Remote Similarity	NPD3168	Discontinued
0.5818	Remote Similarity	NPD5701	Approved
0.5818	Remote Similarity	NPD5697	Approved
0.5789	Remote Similarity	NPD4695	Discontinued
0.5785	Remote Similarity	NPD8273	Phase 1
0.5784	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD28	Approved
0.5769	Remote Similarity	NPD29	Approved
0.5766	Remote Similarity	NPD6881	Approved
0.5766	Remote Similarity	NPD7320	Approved
0.5766	Remote Similarity	NPD6899	Approved
0.5766	Remote Similarity	NPD6011	Approved
0.5743	Remote Similarity	NPD5370	Suspended
0.5714	Remote Similarity	NPD3133	Approved
0.5714	Remote Similarity	NPD3665	Phase 1
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD6372	Approved
0.5714	Remote Similarity	NPD6013	Approved
0.5714	Remote Similarity	NPD3666	Approved
0.5698	Remote Similarity	NPD3197	Phase 1
0.5686	Remote Similarity	NPD3673	Approved
0.5686	Remote Similarity	NPD3672	Approved
0.5682	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD7102	Approved
0.5664	Remote Similarity	NPD7290	Approved
0.5664	Remote Similarity	NPD6883	Approved
0.5664	Remote Similarity	NPD2067	Discontinued
0.566	Remote Similarity	NPD5959	Approved
0.5656	Remote Similarity	NPD7507	Approved
0.5647	Remote Similarity	NPD368	Approved
0.5631	Remote Similarity	NPD8035	Phase 2
0.5631	Remote Similarity	NPD5284	Approved
0.5631	Remote Similarity	NPD8034	Phase 2
0.5631	Remote Similarity	NPD5281	Approved
0.5625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD3172	Approved
0.562	Remote Similarity	NPD7829	Approved
0.562	Remote Similarity	NPD7642	Approved
0.562	Remote Similarity	NPD7830	Approved
0.5619	Remote Similarity	NPD5654	Approved
0.5614	Remote Similarity	NPD8130	Phase 1
0.5614	Remote Similarity	NPD6650	Approved
0.5614	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD6869	Approved
0.5614	Remote Similarity	NPD6847	Approved
0.5614	Remote Similarity	NPD6617	Approved
0.5614	Remote Similarity	NPD6649	Approved
0.5612	Remote Similarity	NPD6695	Phase 3
0.561	Remote Similarity	NPD8074	Phase 3
0.56	Remote Similarity	NPD4519	Discontinued
0.56	Remote Similarity	NPD3618	Phase 1
0.56	Remote Similarity	NPD4623	Approved
0.56	Remote Similarity	NPD5279	Phase 3

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