NPASS Compound

Structure

NPC266650 OpenBabel07101719142D 30 32 0 0 1 0 0 0 0 0999 V2000 -3.8514 -1.2497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1945 -1.7894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0437 -2.9828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7204 -2.5086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5407 -3.2697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6349 -1.9411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7287 -0.7623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5339 -1.3282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1944 -0.9719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6033 -2.2540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1375 -1.2080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6473 -3.1030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3010 -0.8051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1131 -3.3126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8040 -1.3926 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2068 -2.1338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0377 -2.6822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4397 -2.6568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9311 -2.8490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6726 -2.3435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1801 -2.4177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5091 -3.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0794 -2.7103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9284 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9284 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9463 -1.4563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6571 -1.6506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 28 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 14 19 1 0 0 0 0 15 29 1 6 0 0 0 16 17 1 0 0 0 0 16 18 2 0 0 0 0 17 20 2 0 0 0 0 18 22 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 24 30 1 0 0 0 0 25 30 2 0 0 0 0 26 30 2 0 0 0 0 29 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	438.13
Volume:	419.115
LogP:	2.876
LogD:	2.129
LogS:	-2.255
# Rotatable Bonds:	4
TPSA:	122.52
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	4.838
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.985
MDCK Permeability:	1.686220639385283e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	99.33897399902344%
Volume Distribution (VD):	0.494
Pgp-substrate:	0.8066818118095398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.176
CYP1A2-substrate:	0.841
CYP2C19-inhibitor:	0.092
CYP2C19-substrate:	0.554
CYP2C9-inhibitor:	0.54
CYP2C9-substrate:	0.857
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.388
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	1.055
Half-life (T1/2):	0.155

ADMET: Toxicity

hERG Blockers:	0.316
Human Hepatotoxicity (H-HT):	0.517
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.401
Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.931
Carcinogencity:	0.7
Eye Corrosion:	0.009
Eye Irritation:	0.639
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC266650

Natural Product ID:	NPC266650
*Common Name:**	ULRXAJKMNKLJEY-OAHLLOKOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ULRXAJKMNKLJEY-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C21H26O8S/c1-27-20-17-12-14(19(23)21(20)28-2)5-3-4-6-15(29-30(24,25)26)9-7-13-8-10-18(22)16(17)11-13/h8,10-12,15,22-23H,3-7,9H2,1-2H3,(H,24,25,26)/t15-/m1/s1
SMILES:	COc1c2cc(c(c1OC)O)CCCC[C@H](CCc1cc2c(O)cc1)OS(=O)(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152651
PubChem CID:	71454818
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002652] Cyclic diarylheptanoids [CHEMONTID:0003524] Meta,meta-bridged biphenyls

*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
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	barks	n.a.	n.a.	PMID[23066712]
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31026	Myrica rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	8680.0	umolequiv/g	PMID[531553]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	786.9	ug.mL-1	PMID[531553]

☑ 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 NPC266650 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	426
0.1-0.2	1617
0.2-0.3	4799
0.3-0.4	12832
0.4-0.5	5285
0.5-0.6	4269
0.6-0.7	7475
0.7-0.8	4585
0.8-0.85	846
0.85-0.9	498
0.9-0.95	62
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9549	High Similarity	NPC256262
0.9545	High Similarity	NPC170185
0.9173	High Similarity	NPC143483
0.9167	High Similarity	NPC28765
0.9167	High Similarity	NPC154866
0.9137	High Similarity	NPC41782
0.9104	High Similarity	NPC474017
0.9098	High Similarity	NPC170844
0.9098	High Similarity	NPC476968
0.9098	High Similarity	NPC212015
0.9091	High Similarity	NPC266555
0.9091	High Similarity	NPC236791
0.9091	High Similarity	NPC124452
0.9091	High Similarity	NPC21563
0.9091	High Similarity	NPC252131
0.9091	High Similarity	NPC74817
0.9091	High Similarity	NPC324112
0.9091	High Similarity	NPC159968
0.9091	High Similarity	NPC82679
0.9091	High Similarity	NPC293054
0.9091	High Similarity	NPC282000
0.9091	High Similarity	NPC169474
0.9091	High Similarity	NPC246620
0.9065	High Similarity	NPC87725
0.9065	High Similarity	NPC263261
0.9058	High Similarity	NPC70682
0.9058	High Similarity	NPC260741
0.9051	High Similarity	NPC202846
0.9051	High Similarity	NPC133025
0.9051	High Similarity	NPC143139
0.9037	High Similarity	NPC6451
0.903	High Similarity	NPC126836
0.903	High Similarity	NPC51840
0.903	High Similarity	NPC311680
0.903	High Similarity	NPC234488
0.903	High Similarity	NPC299221
0.9023	High Similarity	NPC186843
0.9023	High Similarity	NPC206615
0.9023	High Similarity	NPC472968
0.9023	High Similarity	NPC98631
0.9023	High Similarity	NPC470213
0.9015	High Similarity	NPC78974
0.9015	High Similarity	NPC223953
0.9015	High Similarity	NPC223136
0.9015	High Similarity	NPC28730
0.9015	High Similarity	NPC18924
0.9015	High Similarity	NPC103823
0.9015	High Similarity	NPC214406
0.9015	High Similarity	NPC44748
0.8993	High Similarity	NPC12668
0.8993	High Similarity	NPC308768
0.8993	High Similarity	NPC295719
0.8993	High Similarity	NPC73505
0.8993	High Similarity	NPC165026
0.8993	High Similarity	NPC34431
0.8986	High Similarity	NPC86605
0.8986	High Similarity	NPC156948
0.8986	High Similarity	NPC46277
0.8986	High Similarity	NPC56329
0.8986	High Similarity	NPC3072
0.8986	High Similarity	NPC242715
0.8986	High Similarity	NPC301765
0.8978	High Similarity	NPC112939
0.8978	High Similarity	NPC473413
0.8978	High Similarity	NPC474206
0.8978	High Similarity	NPC112246
0.8978	High Similarity	NPC158142
0.8978	High Similarity	NPC294884
0.8978	High Similarity	NPC69029
0.8978	High Similarity	NPC121812
0.8978	High Similarity	NPC200557
0.8978	High Similarity	NPC108198
0.8978	High Similarity	NPC94750
0.8978	High Similarity	NPC241241
0.8978	High Similarity	NPC10314
0.8978	High Similarity	NPC470356
0.8971	High Similarity	NPC32778
0.8971	High Similarity	NPC475840
0.8971	High Similarity	NPC158331
0.8963	High Similarity	NPC45715
0.8963	High Similarity	NPC232275
0.8963	High Similarity	NPC15543
0.8963	High Similarity	NPC474356
0.8963	High Similarity	NPC12275
0.8963	High Similarity	NPC470095
0.8963	High Similarity	NPC470096
0.8955	High Similarity	NPC58164
0.8955	High Similarity	NPC10225
0.8947	High Similarity	NPC127587
0.8947	High Similarity	NPC242032
0.8939	High Similarity	NPC221077
0.8939	High Similarity	NPC17943
0.8939	High Similarity	NPC208950
0.8939	High Similarity	NPC299584
0.8939	High Similarity	NPC475169
0.8939	High Similarity	NPC82483
0.8939	High Similarity	NPC116907
0.8939	High Similarity	NPC234400
0.8939	High Similarity	NPC60885
0.8939	High Similarity	NPC233410
0.8939	High Similarity	NPC298757
0.8939	High Similarity	NPC57490
0.8939	High Similarity	NPC117214
0.8939	High Similarity	NPC193544
0.8939	High Similarity	NPC105925
0.8939	High Similarity	NPC251855
0.8939	High Similarity	NPC203133
0.8939	High Similarity	NPC265483
0.8939	High Similarity	NPC472093
0.8929	High Similarity	NPC19158
0.8929	High Similarity	NPC35216
0.8921	High Similarity	NPC243759
0.8921	High Similarity	NPC79622
0.8921	High Similarity	NPC32630
0.8921	High Similarity	NPC230124
0.8921	High Similarity	NPC212942
0.8921	High Similarity	NPC29868
0.8921	High Similarity	NPC220344
0.8921	High Similarity	NPC275061
0.8921	High Similarity	NPC6300
0.8921	High Similarity	NPC184613
0.8921	High Similarity	NPC22517
0.8921	High Similarity	NPC132804
0.8921	High Similarity	NPC105847
0.8921	High Similarity	NPC218131
0.8921	High Similarity	NPC471183
0.8921	High Similarity	NPC114171
0.8921	High Similarity	NPC243996
0.8913	High Similarity	NPC30632
0.8913	High Similarity	NPC162659
0.8913	High Similarity	NPC227503
0.8913	High Similarity	NPC470802
0.8913	High Similarity	NPC474639
0.8913	High Similarity	NPC306441
0.8913	High Similarity	NPC270456
0.8913	High Similarity	NPC265433
0.8913	High Similarity	NPC16435
0.8913	High Similarity	NPC230734
0.8913	High Similarity	NPC472336
0.8913	High Similarity	NPC248727
0.8913	High Similarity	NPC472334
0.8905	High Similarity	NPC206737
0.8905	High Similarity	NPC326095
0.8905	High Similarity	NPC56764
0.8905	High Similarity	NPC469659
0.8905	High Similarity	NPC7515
0.8905	High Similarity	NPC244983
0.8905	High Similarity	NPC287745
0.8905	High Similarity	NPC125649
0.8905	High Similarity	NPC276026
0.8905	High Similarity	NPC160697
0.8905	High Similarity	NPC289258
0.8905	High Similarity	NPC188378
0.8905	High Similarity	NPC555
0.8897	High Similarity	NPC204215
0.8897	High Similarity	NPC175067
0.8897	High Similarity	NPC7903
0.8897	High Similarity	NPC253105
0.8897	High Similarity	NPC184447
0.8897	High Similarity	NPC16208
0.8897	High Similarity	NPC35932
0.8897	High Similarity	NPC201587
0.8897	High Similarity	NPC160991
0.8889	High Similarity	NPC224157
0.8889	High Similarity	NPC192687
0.8881	High Similarity	NPC266691
0.8881	High Similarity	NPC474799
0.8881	High Similarity	NPC260397
0.8873	High Similarity	NPC280092
0.8873	High Similarity	NPC12641
0.8873	High Similarity	NPC473108
0.8873	High Similarity	NPC45257
0.8873	High Similarity	NPC50250
0.8873	High Similarity	NPC93323
0.8872	High Similarity	NPC76451
0.8865	High Similarity	NPC59841
0.8865	High Similarity	NPC175838
0.8865	High Similarity	NPC204347
0.8865	High Similarity	NPC2613
0.8865	High Similarity	NPC475891
0.8864	High Similarity	NPC206487
0.8864	High Similarity	NPC5796
0.8857	High Similarity	NPC259519
0.8857	High Similarity	NPC309124
0.8857	High Similarity	NPC160283
0.8857	High Similarity	NPC184797
0.8857	High Similarity	NPC254759
0.8849	High Similarity	NPC230919
0.8849	High Similarity	NPC200935
0.8849	High Similarity	NPC103976
0.8849	High Similarity	NPC266006
0.8849	High Similarity	NPC6262
0.8849	High Similarity	NPC73535
0.8849	High Similarity	NPC272157
0.8849	High Similarity	NPC266453
0.8849	High Similarity	NPC90615
0.8849	High Similarity	NPC25111
0.8849	High Similarity	NPC201145
0.8849	High Similarity	NPC22902
0.8849	High Similarity	NPC477938

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 NPC266650 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	907
0.2-0.3	1945
0.3-0.4	2776
0.4-0.5	1582
0.5-0.6	897
0.6-0.7	586
0.7-0.8	96
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9098	High Similarity	NPD3027	Phase 3
0.8623	High Similarity	NPD1612	Clinical (unspecified phase)
0.8623	High Similarity	NPD1613	Approved
0.8467	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD3018	Phase 2
0.8085	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD2982	Phase 2
0.7971	Intermediate Similarity	NPD2983	Phase 2
0.7943	Intermediate Similarity	NPD4908	Phase 1
0.7935	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD2981	Phase 2
0.7887	Intermediate Similarity	NPD4625	Phase 3
0.7871	Intermediate Similarity	NPD1934	Approved
0.7848	Intermediate Similarity	NPD6234	Discontinued
0.7826	Intermediate Similarity	NPD1610	Phase 2
0.782	Intermediate Similarity	NPD5283	Phase 1
0.7803	Intermediate Similarity	NPD228	Approved
0.777	Intermediate Similarity	NPD3540	Phase 1
0.7756	Intermediate Similarity	NPD37	Approved
0.7703	Intermediate Similarity	NPD3539	Phase 1
0.7702	Intermediate Similarity	NPD6232	Discontinued
0.7667	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1548	Phase 1
0.7622	Intermediate Similarity	NPD2861	Phase 2
0.7613	Intermediate Similarity	NPD1653	Approved
0.761	Intermediate Similarity	NPD4967	Phase 2
0.761	Intermediate Similarity	NPD4966	Approved
0.761	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD4965	Approved
0.7607	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6166	Phase 2
0.7603	Intermediate Similarity	NPD3620	Phase 2
0.7603	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4060	Phase 1
0.7595	Intermediate Similarity	NPD2801	Approved
0.7589	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7473	Discontinued
0.7552	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD3021	Approved
0.7519	Intermediate Similarity	NPD3022	Approved
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.7515	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD3882	Suspended
0.747	Intermediate Similarity	NPD5844	Phase 1
0.7466	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD4749	Approved
0.7453	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6674	Discontinued
0.7425	Intermediate Similarity	NPD7074	Phase 3
0.741	Intermediate Similarity	NPD3818	Discontinued
0.7365	Intermediate Similarity	NPD7054	Approved
0.7355	Intermediate Similarity	NPD1511	Approved
0.7342	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3817	Phase 2
0.7324	Intermediate Similarity	NPD3705	Approved
0.7321	Intermediate Similarity	NPD7472	Approved
0.7317	Intermediate Similarity	NPD7199	Phase 2
0.7303	Intermediate Similarity	NPD7266	Discontinued
0.7303	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD8651	Approved
0.7273	Intermediate Similarity	NPD3892	Phase 2
0.7267	Intermediate Similarity	NPD1465	Phase 2
0.7261	Intermediate Similarity	NPD1512	Approved
0.7256	Intermediate Similarity	NPD5494	Approved
0.7248	Intermediate Similarity	NPD1558	Phase 1
0.7239	Intermediate Similarity	NPD4055	Discovery
0.7239	Intermediate Similarity	NPD7075	Discontinued
0.7233	Intermediate Similarity	NPD4005	Discontinued
0.723	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4536	Approved
0.7219	Intermediate Similarity	NPD4538	Approved
0.7208	Intermediate Similarity	NPD5177	Phase 3
0.7208	Intermediate Similarity	NPD3060	Approved
0.7203	Intermediate Similarity	NPD1091	Approved
0.72	Intermediate Similarity	NPD3657	Discovery
0.7197	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7157	Approved
0.7188	Intermediate Similarity	NPD4675	Approved
0.7188	Intermediate Similarity	NPD4678	Approved
0.7179	Intermediate Similarity	NPD7124	Phase 2
0.7176	Intermediate Similarity	NPD6797	Phase 2
0.7152	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6559	Discontinued
0.7135	Intermediate Similarity	NPD7251	Discontinued
0.7134	Intermediate Similarity	NPD4357	Discontinued
0.7133	Intermediate Similarity	NPD2238	Phase 2
0.7132	Intermediate Similarity	NPD4750	Phase 3
0.7124	Intermediate Similarity	NPD2935	Discontinued
0.7121	Intermediate Similarity	NPD940	Approved
0.7121	Intermediate Similarity	NPD846	Approved
0.7117	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1357	Approved
0.7108	Intermediate Similarity	NPD6959	Discontinued
0.7101	Intermediate Similarity	NPD7843	Approved
0.7097	Intermediate Similarity	NPD1652	Phase 2
0.7093	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7808	Phase 3
0.7092	Intermediate Similarity	NPD5536	Phase 2
0.7086	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5124	Phase 1
0.7083	Intermediate Similarity	NPD422	Phase 1
0.7076	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6671	Approved
0.7066	Intermediate Similarity	NPD7229	Phase 3
0.7063	Intermediate Similarity	NPD4626	Approved
0.7059	Intermediate Similarity	NPD5960	Phase 3
0.7059	Intermediate Similarity	NPD5588	Approved
0.7059	Intermediate Similarity	NPD2684	Approved
0.7059	Intermediate Similarity	NPD1510	Phase 2
0.7055	Intermediate Similarity	NPD7819	Suspended
0.7055	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6331	Phase 2
0.7045	Intermediate Similarity	NPD1242	Phase 1
0.7044	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7240	Approved
0.703	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7212	Phase 2
0.7025	Intermediate Similarity	NPD7213	Phase 3
0.702	Intermediate Similarity	NPD1240	Approved
0.7006	Intermediate Similarity	NPD2219	Phase 1
0.7006	Intermediate Similarity	NPD2677	Approved
0.7006	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6801	Discontinued
0.6993	Remote Similarity	NPD6111	Discontinued
0.6987	Remote Similarity	NPD4236	Phase 3
0.6987	Remote Similarity	NPD4237	Approved
0.6985	Remote Similarity	NPD290	Approved
0.6981	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7447	Phase 1
0.6974	Remote Similarity	NPD230	Phase 1
0.6974	Remote Similarity	NPD6355	Discontinued
0.6971	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7768	Phase 2
0.6968	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5762	Approved
0.6968	Remote Similarity	NPD5763	Approved
0.6962	Remote Similarity	NPD5058	Phase 3
0.6959	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2674	Phase 3
0.6951	Remote Similarity	NPD2978	Approved
0.6951	Remote Similarity	NPD2977	Approved
0.6951	Remote Similarity	NPD8455	Phase 2
0.695	Remote Similarity	NPD6387	Discontinued
0.6949	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6696	Suspended
0.6933	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6072	Discontinued
0.6928	Remote Similarity	NPD4097	Suspended
0.6928	Remote Similarity	NPD1607	Approved
0.6923	Remote Similarity	NPD2424	Discontinued
0.6923	Remote Similarity	NPD1549	Phase 2
0.6918	Remote Similarity	NPD7041	Phase 2
0.6918	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD8053	Approved
0.6914	Remote Similarity	NPD8054	Approved
0.6908	Remote Similarity	NPD943	Approved
0.6903	Remote Similarity	NPD2438	Suspended
0.6903	Remote Similarity	NPD6100	Approved
0.6903	Remote Similarity	NPD6099	Approved
0.6897	Remote Similarity	NPD7549	Discontinued
0.6893	Remote Similarity	NPD7906	Approved
0.6892	Remote Similarity	NPD3094	Phase 2
0.6887	Remote Similarity	NPD5109	Approved
0.6887	Remote Similarity	NPD5111	Phase 2
0.6887	Remote Similarity	NPD6798	Discontinued
0.6887	Remote Similarity	NPD5110	Phase 2
0.6875	Remote Similarity	NPD1651	Approved
0.6875	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4123	Phase 3
0.6875	Remote Similarity	NPD2534	Approved
0.6875	Remote Similarity	NPD2532	Approved
0.6875	Remote Similarity	NPD2533	Approved
0.6875	Remote Similarity	NPD5691	Approved
0.6871	Remote Similarity	NPD1669	Approved
0.6863	Remote Similarity	NPD5735	Approved
0.6859	Remote Similarity	NPD1375	Discontinued
0.6857	Remote Similarity	NPD7635	Approved
0.6846	Remote Similarity	NPD6584	Phase 3
0.6842	Remote Similarity	NPD3020	Approved
0.6842	Remote Similarity	NPD4062	Phase 3
0.6839	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4535	Phase 3
0.6835	Remote Similarity	NPD3750	Approved
0.6835	Remote Similarity	NPD4628	Phase 3
0.6835	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4110	Phase 3
0.6829	Remote Similarity	NPD7411	Suspended
0.6829	Remote Similarity	NPD5090	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