NPASS Compound

Structure

NPC476270 OpenBabel07101718332D 25 27 0 0 1 0 0 0 0 0999 V2000 4.7662 -2.4045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0444 -5.8579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2879 -1.9824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -4.2943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7941 -0.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6200 -3.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4743 -1.5237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1906 -4.7943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8632 -0.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -1.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8609 -0.6012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7690 -2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1934 -4.8690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7123 -2.8001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7124 -2.8151 0.0000 C 0 0 2 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 0.2626 -4.5037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4176 -3.7706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0355 -3.7464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2707 -1.5133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3008 -5.3299 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9910 -4.0412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2353 -4.3463 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 1 0 0 0 0 2 13 1 0 0 0 0 3 14 2 0 0 0 0 4 6 1 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 9 1 0 0 0 0 6 12 1 0 0 0 0 7 12 2 0 0 0 0 8 13 2 0 0 0 0 9 20 1 0 0 0 0 10 16 1 0 0 0 0 11 21 1 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 10 1 1 0 0 0 15 18 1 0 0 0 0 16 20 1 1 0 0 0 16 25 1 0 0 0 0 17 22 2 0 0 0 0 18 17 1 6 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 11 1 1 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.18
Volume:	359.576
LogP:	2.442
LogD:	2.004
LogS:	-3.953
# Rotatable Bonds:	1
TPSA:	76.13
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.342
Synthetic Accessibility Score:	5.063
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.679
MDCK Permeability:	1.8476721379556693e-05
Pgp-inhibitor:	0.169
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.124
20% Bioavailability (F20%):	0.413
30% Bioavailability (F30%):	0.632

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.186
Plasma Protein Binding (PPB):	90.39366912841797%
Volume Distribution (VD):	1.461
Pgp-substrate:	6.67724609375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.195
CYP2C19-inhibitor:	0.274
CYP2C19-substrate:	0.332
CYP2C9-inhibitor:	0.391
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.651
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	8.559
Half-life (T1/2):	0.515

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.549
Drug-inuced Liver Injury (DILI):	0.254
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.13
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.963
Carcinogencity:	0.164
Eye Corrosion:	0.126
Eye Irritation:	0.347
Respiratory Toxicity:	0.807

Download Data

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

Natural Product: NPC476270

Natural Product ID:	NPC476270
*Common Name:**	Durumolide K
IUPAC Name:	n.a.
Synonyms:	durumolide K
Standard InCHIKey:	JPIGOPYINYLNIZ-KMKNQKDISA-N
Standard InCHI:	InChI=1S/C20H26O5/c1-12-6-4-8-13(2)17(22)18-15(14(3)19(23)24-18)10-16-20(11-21,25-16)9-5-7-12/h7-8,15-16,18,21H,3-6,9-11H2,1-2H3/b12-7+,13-8+/t15-,16-,18-,20+/m1/s1
SMILES:	CC1=CCCC2(C(O2)CC3C(C(=O)C(=CCC1)C)OC(=O)C3=C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL560157
PubChem CID:	44188459
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19177635]
NPO5325	Lobophytum durum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19433363]
NPO5325	Lobophytum durum	Species	Alcyoniidae	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
Others	2

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	Inhibition	=	5.7	%	PMID[554469]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	71.6	%	PMID[554469]

☑ 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 NPC476270 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	241
0.1-0.2	1427
0.2-0.3	5167
0.3-0.4	8976
0.4-0.5	14211
0.5-0.6	7507
0.6-0.7	3728
0.7-0.8	1205
0.8-0.85	169
0.85-0.9	59
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9247	High Similarity	NPC212486
0.9082	High Similarity	NPC324017
0.9082	High Similarity	NPC320019
0.9053	High Similarity	NPC270013
0.9053	High Similarity	NPC14961
0.9032	High Similarity	NPC329857
0.9032	High Similarity	NPC469718
0.898	High Similarity	NPC474339
0.898	High Similarity	NPC15993
0.898	High Similarity	NPC201718
0.898	High Similarity	NPC164598
0.8947	High Similarity	NPC474035
0.8947	High Similarity	NPC81386
0.8936	High Similarity	NPC184463
0.8911	High Similarity	NPC477513
0.89	High Similarity	NPC474741
0.8889	High Similarity	NPC474747
0.8866	High Similarity	NPC328562
0.8866	High Similarity	NPC323421
0.8854	High Similarity	NPC474947
0.8842	High Similarity	NPC475912
0.8817	High Similarity	NPC202672
0.88	High Similarity	NPC475871
0.88	High Similarity	NPC475945
0.88	High Similarity	NPC475873
0.8788	High Similarity	NPC47880
0.8776	High Similarity	NPC473326
0.8763	High Similarity	NPC476315
0.8763	High Similarity	NPC31645
0.8763	High Similarity	NPC476275
0.875	High Similarity	NPC190294
0.8737	High Similarity	NPC208886
0.8737	High Similarity	NPC30515
0.8737	High Similarity	NPC12172
0.8723	High Similarity	NPC307411
0.8713	High Similarity	NPC472756
0.87	High Similarity	NPC471148
0.87	High Similarity	NPC149371
0.8687	High Similarity	NPC288876
0.8687	High Similarity	NPC475949
0.866	High Similarity	NPC36954
0.8646	High Similarity	NPC81419
0.8646	High Similarity	NPC476300
0.8646	High Similarity	NPC179746
0.8632	High Similarity	NPC251385
0.8632	High Similarity	NPC51004
0.8632	High Similarity	NPC49342
0.8614	High Similarity	NPC472755
0.86	High Similarity	NPC110443
0.86	High Similarity	NPC133907
0.86	High Similarity	NPC46998
0.86	High Similarity	NPC128733
0.86	High Similarity	NPC474742
0.86	High Similarity	NPC185141
0.86	High Similarity	NPC472753
0.8586	High Similarity	NPC471144
0.8586	High Similarity	NPC474213
0.8571	High Similarity	NPC473859
0.8571	High Similarity	NPC279621
0.8558	High Similarity	NPC38154
0.8557	High Similarity	NPC303942
0.8557	High Similarity	NPC57405
0.8542	High Similarity	NPC20713
0.8526	High Similarity	NPC173926
0.8526	High Similarity	NPC151770
0.8515	High Similarity	NPC472754
0.8511	High Similarity	NPC231889
0.8469	Intermediate Similarity	NPC475659
0.8454	Intermediate Similarity	NPC228451
0.8454	Intermediate Similarity	NPC475838
0.8454	Intermediate Similarity	NPC273579
0.8454	Intermediate Similarity	NPC295204
0.8454	Intermediate Similarity	NPC125674
0.8454	Intermediate Similarity	NPC162205
0.8454	Intermediate Similarity	NPC288240
0.8447	Intermediate Similarity	NPC243998
0.8438	Intermediate Similarity	NPC475748
0.8438	Intermediate Similarity	NPC476004
0.8438	Intermediate Similarity	NPC474761
0.8438	Intermediate Similarity	NPC473619
0.8431	Intermediate Similarity	NPC472747
0.8431	Intermediate Similarity	NPC472750
0.8421	Intermediate Similarity	NPC281516
0.8416	Intermediate Similarity	NPC264477
0.8416	Intermediate Similarity	NPC477511
0.8384	Intermediate Similarity	NPC76862
0.8384	Intermediate Similarity	NPC39859
0.8384	Intermediate Similarity	NPC470883
0.8384	Intermediate Similarity	NPC476009
0.8384	Intermediate Similarity	NPC158416
0.8384	Intermediate Similarity	NPC17585
0.8367	Intermediate Similarity	NPC473316
0.8367	Intermediate Similarity	NPC474247
0.8367	Intermediate Similarity	NPC121825
0.8367	Intermediate Similarity	NPC473330
0.8351	Intermediate Similarity	NPC70251
0.8351	Intermediate Similarity	NPC475881
0.8351	Intermediate Similarity	NPC473321
0.835	Intermediate Similarity	NPC472748
0.835	Intermediate Similarity	NPC100487
0.8333	Intermediate Similarity	NPC474951
0.8333	Intermediate Similarity	NPC166919
0.8316	Intermediate Similarity	NPC186148
0.8298	Intermediate Similarity	NPC149725
0.8298	Intermediate Similarity	NPC47958
0.8298	Intermediate Similarity	NPC304509
0.8283	Intermediate Similarity	NPC475900
0.8283	Intermediate Similarity	NPC471141
0.828	Intermediate Similarity	NPC272814
0.8269	Intermediate Similarity	NPC223450
0.8269	Intermediate Similarity	NPC472749
0.8269	Intermediate Similarity	NPC472751
0.8265	Intermediate Similarity	NPC475302
0.8265	Intermediate Similarity	NPC469692
0.8265	Intermediate Similarity	NPC469645
0.8265	Intermediate Similarity	NPC165383
0.8247	Intermediate Similarity	NPC65359
0.8235	Intermediate Similarity	NPC473332
0.8229	Intermediate Similarity	NPC58219
0.8229	Intermediate Similarity	NPC177629
0.8218	Intermediate Similarity	NPC187268
0.82	Intermediate Similarity	NPC230800
0.8182	Intermediate Similarity	NPC471146
0.8182	Intermediate Similarity	NPC71589
0.8173	Intermediate Similarity	NPC471143
0.8173	Intermediate Similarity	NPC203659
0.8173	Intermediate Similarity	NPC477510
0.8163	Intermediate Similarity	NPC469627
0.8163	Intermediate Similarity	NPC329952
0.8155	Intermediate Similarity	NPC189609
0.8155	Intermediate Similarity	NPC140591
0.8155	Intermediate Similarity	NPC225353
0.8155	Intermediate Similarity	NPC303653
0.8155	Intermediate Similarity	NPC291500
0.8155	Intermediate Similarity	NPC197835
0.8144	Intermediate Similarity	NPC295312
0.8144	Intermediate Similarity	NPC92974
0.8144	Intermediate Similarity	NPC474032
0.8137	Intermediate Similarity	NPC477512
0.8131	Intermediate Similarity	NPC5103
0.8125	Intermediate Similarity	NPC5130
0.8125	Intermediate Similarity	NPC248602
0.8125	Intermediate Similarity	NPC475703
0.8125	Intermediate Similarity	NPC179659
0.8119	Intermediate Similarity	NPC471140
0.8108	Intermediate Similarity	NPC475401
0.8105	Intermediate Similarity	NPC319795
0.8105	Intermediate Similarity	NPC21469
0.8105	Intermediate Similarity	NPC50362
0.8105	Intermediate Similarity	NPC38468
0.81	Intermediate Similarity	NPC471142
0.81	Intermediate Similarity	NPC107476
0.8095	Intermediate Similarity	NPC54737
0.8091	Intermediate Similarity	NPC270478
0.8085	Intermediate Similarity	NPC11620
0.8077	Intermediate Similarity	NPC110989
0.8061	Intermediate Similarity	NPC62815
0.8061	Intermediate Similarity	NPC144133
0.8061	Intermediate Similarity	NPC475855
0.8061	Intermediate Similarity	NPC179394
0.8041	Intermediate Similarity	NPC476706
0.8041	Intermediate Similarity	NPC473715
0.8041	Intermediate Similarity	NPC476707
0.8041	Intermediate Similarity	NPC476704
0.8041	Intermediate Similarity	NPC153805
0.8041	Intermediate Similarity	NPC475902
0.8039	Intermediate Similarity	NPC161855
0.8039	Intermediate Similarity	NPC300584
0.8036	Intermediate Similarity	NPC477092
0.8021	Intermediate Similarity	NPC470242
0.8021	Intermediate Similarity	NPC474949
0.8021	Intermediate Similarity	NPC50637
0.8021	Intermediate Similarity	NPC475019
0.802	Intermediate Similarity	NPC477921
0.802	Intermediate Similarity	NPC473291
0.8019	Intermediate Similarity	NPC474421
0.8019	Intermediate Similarity	NPC72813
0.8019	Intermediate Similarity	NPC326994
0.8019	Intermediate Similarity	NPC324327
0.8019	Intermediate Similarity	NPC194620
0.8018	Intermediate Similarity	NPC475305
0.8	Intermediate Similarity	NPC474780
0.8	Intermediate Similarity	NPC72464
0.8	Intermediate Similarity	NPC469632
0.8	Intermediate Similarity	NPC471147
0.8	Intermediate Similarity	NPC140543
0.7982	Intermediate Similarity	NPC66108
0.7981	Intermediate Similarity	NPC39996
0.7981	Intermediate Similarity	NPC86077
0.798	Intermediate Similarity	NPC470373
0.798	Intermediate Similarity	NPC476705
0.798	Intermediate Similarity	NPC470379
0.7961	Intermediate Similarity	NPC475053
0.7944	Intermediate Similarity	NPC169888
0.7944	Intermediate Similarity	NPC474664
0.7944	Intermediate Similarity	NPC233379
0.7944	Intermediate Similarity	NPC55972
0.7944	Intermediate Similarity	NPC14862
0.7944	Intermediate Similarity	NPC327286
0.7941	Intermediate Similarity	NPC40812

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 NPC476270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	2079
0.2-0.3	3735
0.3-0.4	2036
0.4-0.5	694
0.5-0.6	265
0.6-0.7	113
0.7-0.8	7
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8105	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6698	Approved
0.8061	Intermediate Similarity	NPD46	Approved
0.785	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD7838	Discovery
0.7636	Intermediate Similarity	NPD6371	Approved
0.7573	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD1695	Approved
0.7282	Intermediate Similarity	NPD7983	Approved
0.7257	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5282	Discontinued
0.7064	Intermediate Similarity	NPD5344	Discontinued
0.6991	Remote Similarity	NPD6686	Approved
0.6917	Remote Similarity	NPD6319	Approved
0.6881	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4225	Approved
0.6838	Remote Similarity	NPD4632	Approved
0.6807	Remote Similarity	NPD7115	Discovery
0.6783	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD5697	Approved
0.6752	Remote Similarity	NPD8297	Approved
0.6752	Remote Similarity	NPD6053	Discontinued
0.6748	Remote Similarity	NPD7642	Approved
0.6733	Remote Similarity	NPD6435	Approved
0.6727	Remote Similarity	NPD5696	Approved
0.6698	Remote Similarity	NPD5785	Approved
0.6696	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6881	Approved
0.6696	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD6110	Phase 1
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6641	Remote Similarity	NPD7260	Phase 2
0.664	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6638	Remote Similarity	NPD6012	Approved
0.6638	Remote Similarity	NPD6014	Approved
0.6638	Remote Similarity	NPD6013	Approved
0.6638	Remote Similarity	NPD6372	Approved
0.6638	Remote Similarity	NPD6373	Approved
0.6613	Remote Similarity	NPD7604	Phase 2
0.6609	Remote Similarity	NPD5701	Approved
0.6587	Remote Similarity	NPD7078	Approved
0.6585	Remote Similarity	NPD8516	Approved
0.6585	Remote Similarity	NPD8515	Approved
0.6585	Remote Similarity	NPD8513	Phase 3
0.6585	Remote Similarity	NPD6015	Approved
0.6585	Remote Similarity	NPD5983	Phase 2
0.6585	Remote Similarity	NPD6016	Approved
0.6585	Remote Similarity	NPD8517	Approved
0.6581	Remote Similarity	NPD6883	Approved
0.6581	Remote Similarity	NPD7290	Approved
0.6581	Remote Similarity	NPD7102	Approved
0.6581	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5779	Approved
0.6574	Remote Similarity	NPD5778	Approved
0.6552	Remote Similarity	NPD6011	Approved
0.6552	Remote Similarity	NPD7320	Approved
0.6538	Remote Similarity	NPD5363	Approved
0.6535	Remote Similarity	NPD5368	Approved
0.6535	Remote Similarity	NPD7736	Approved
0.6532	Remote Similarity	NPD6370	Approved
0.6532	Remote Similarity	NPD5988	Approved
0.6525	Remote Similarity	NPD6869	Approved
0.6525	Remote Similarity	NPD6617	Approved
0.6525	Remote Similarity	NPD6847	Approved
0.6525	Remote Similarity	NPD8130	Phase 1
0.6505	Remote Similarity	NPD7154	Phase 3
0.6504	Remote Similarity	NPD6059	Approved
0.6486	Remote Similarity	NPD6084	Phase 2
0.6486	Remote Similarity	NPD6083	Phase 2
0.648	Remote Similarity	NPD7829	Approved
0.648	Remote Similarity	NPD8328	Phase 3
0.648	Remote Similarity	NPD7830	Approved
0.6476	Remote Similarity	NPD4249	Approved
0.6476	Remote Similarity	NPD5786	Approved
0.6475	Remote Similarity	NPD7641	Discontinued
0.6471	Remote Similarity	NPD5369	Approved
0.6471	Remote Similarity	NPD6882	Approved
0.6462	Remote Similarity	NPD6845	Suspended
0.6457	Remote Similarity	NPD8293	Discontinued
0.6455	Remote Similarity	NPD5695	Phase 3
0.6415	Remote Similarity	NPD4250	Approved
0.6415	Remote Similarity	NPD4251	Approved
0.64	Remote Similarity	NPD8080	Discontinued
0.6381	Remote Similarity	NPD1694	Approved
0.6378	Remote Similarity	NPD6336	Discontinued
0.6378	Remote Similarity	NPD7507	Approved
0.6328	Remote Similarity	NPD8074	Phase 3
0.6325	Remote Similarity	NPD6412	Phase 2
0.6325	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.632	Remote Similarity	NPD8444	Approved
0.6311	Remote Similarity	NPD6274	Approved
0.6306	Remote Similarity	NPD4629	Approved
0.6306	Remote Similarity	NPD5210	Approved
0.6303	Remote Similarity	NPD4634	Approved
0.6296	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6101	Approved
0.6283	Remote Similarity	NPD7638	Approved
0.6277	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD2204	Approved
0.625	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4270	Approved
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7839	Suspended
0.625	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4756	Discovery
0.6231	Remote Similarity	NPD7319	Approved
0.6228	Remote Similarity	NPD5286	Approved
0.6228	Remote Similarity	NPD7639	Approved
0.6228	Remote Similarity	NPD5285	Approved
0.6228	Remote Similarity	NPD7640	Approved
0.6228	Remote Similarity	NPD4696	Approved
0.6226	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4822	Approved
0.6214	Remote Similarity	NPD4821	Approved
0.6214	Remote Similarity	NPD4819	Approved
0.6214	Remote Similarity	NPD4820	Approved
0.6195	Remote Similarity	NPD4755	Approved
0.619	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5362	Discontinued
0.6182	Remote Similarity	NPD6411	Approved
0.6182	Remote Similarity	NPD5693	Phase 1
0.616	Remote Similarity	NPD7100	Approved
0.616	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD5141	Approved
0.6129	Remote Similarity	NPD6317	Approved
0.6129	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6399	Phase 3
0.6124	Remote Similarity	NPD8273	Phase 1
0.6124	Remote Similarity	NPD8451	Approved
0.6121	Remote Similarity	NPD5224	Approved
0.6121	Remote Similarity	NPD4633	Approved
0.6121	Remote Similarity	NPD5226	Approved
0.6121	Remote Similarity	NPD5225	Approved
0.6095	Remote Similarity	NPD5209	Approved
0.6087	Remote Similarity	NPD4700	Approved
0.608	Remote Similarity	NPD6314	Approved
0.608	Remote Similarity	NPD6313	Approved
0.608	Remote Similarity	NPD6335	Approved
0.6077	Remote Similarity	NPD8448	Approved
0.6068	Remote Similarity	NPD5174	Approved
0.6068	Remote Similarity	NPD5175	Approved
0.6063	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6921	Approved
0.6058	Remote Similarity	NPD4252	Approved
0.6055	Remote Similarity	NPD6672	Approved
0.6055	Remote Similarity	NPD5737	Approved
0.6042	Remote Similarity	NPD7331	Phase 2
0.6034	Remote Similarity	NPD5223	Approved
0.6031	Remote Similarity	NPD6033	Approved
0.6019	Remote Similarity	NPD4271	Approved
0.6019	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4268	Approved
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD3197	Phase 1
0.5965	Remote Similarity	NPD5221	Approved
0.5965	Remote Similarity	NPD5222	Approved
0.5965	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD4697	Phase 3
0.5956	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.594	Remote Similarity	NPD5956	Approved
0.594	Remote Similarity	NPD8390	Approved
0.594	Remote Similarity	NPD8392	Approved
0.594	Remote Similarity	NPD8391	Approved
0.5938	Remote Similarity	NPD7341	Phase 2
0.5938	Remote Similarity	NPD6908	Approved
0.5938	Remote Similarity	NPD6909	Approved
0.5923	Remote Similarity	NPD8299	Approved
0.5923	Remote Similarity	NPD8342	Approved
0.5923	Remote Similarity	NPD8340	Approved
0.5923	Remote Similarity	NPD8341	Approved
0.592	Remote Similarity	NPD6868	Approved
0.5913	Remote Similarity	NPD7902	Approved
0.5913	Remote Similarity	NPD5173	Approved
0.5905	Remote Similarity	NPD4695	Discontinued
0.5902	Remote Similarity	NPD2067	Discontinued
0.5887	Remote Similarity	NPD8133	Approved
0.5882	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8415	Approved
0.5876	Remote Similarity	NPD3704	Approved
0.5873	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD5279	Phase 3
0.5868	Remote Similarity	NPD5128	Approved
0.5868	Remote Similarity	NPD4729	Approved
0.5868	Remote Similarity	NPD4730	Approved
0.5856	Remote Similarity	NPD6080	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