NPASS Compound

Structure

CID317573 OpenBabel06191716142D 34 39 0 0 1 0 0 0 0 0999 V2000 -3.7327 -5.4095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9380 -4.0333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1600 1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3238 -0.3342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1948 -2.0615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6533 0.3229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5747 -0.5492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7804 -3.0249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9070 -2.5208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9066 0.5045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7800 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4002 -1.5119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5268 -1.0078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1603 -1.5124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7129 -1.0084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2737 -3.0244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6769 -0.3907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7326 -4.4919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6536 -2.5206 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0334 0.0002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9069 -1.5124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2738 -4.0329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5270 -3.0247 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5271 -4.0331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1601 0.5042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4003 -2.5203 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6535 -1.5121 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7801 -1.0080 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0335 -1.0083 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7131 -0.0001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0684 -4.4915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5515 0.4838 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 -5.4005 -4.5372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 18 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 28 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 15 30 1 0 0 0 0 16 22 1 0 0 0 0 16 26 1 0 0 0 0 17 29 1 0 0 0 0 17 33 1 0 0 0 0 19 23 1 0 0 0 0 19 27 1 6 0 0 0 20 25 1 0 0 0 0 20 29 1 1 0 0 0 21 28 1 1 0 0 0 21 29 1 0 0 0 0 22 31 2 0 0 0 0 22 34 1 0 0 0 0 23 24 1 0 0 0 0 23 26 1 1 0 0 0 24 18 1 6 0 0 0 24 34 1 0 0 0 0 25 30 1 0 0 0 0 26 5 1 1 0 0 0 27 28 1 1 0 0 0 28 7 1 1 0 0 0 29 14 1 6 0 0 0 30 32 1 6 0 0 0 30 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	505.985
LogP:	5.802
LogD:	5.074
LogS:	-5.852
# Rotatable Bonds:	1
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	6.435
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.299
MDCK Permeability:	3.337459929753095e-05
Pgp-inhibitor:	0.105
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.214
30% Bioavailability (F30%):	0.898

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	89.26439666748047%
Volume Distribution (VD):	1.165
Pgp-substrate:	4.475715160369873%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.805
CYP2C19-inhibitor:	0.169
CYP2C19-substrate:	0.927
CYP2C9-inhibitor:	0.329
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.363
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.782

ADMET: Excretion

Clearance (CL):	6.572
Half-life (T1/2):	0.171

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.353
Drug-inuced Liver Injury (DILI):	0.235
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.08
Maximum Recommended Daily Dose:	0.801
Skin Sensitization:	0.309
Carcinogencity:	0.147
Eye Corrosion:	0.018
Eye Irritation:	0.023
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC317573

Natural Product ID:	NPC317573
*Common Name:**	Lippiolide
IUPAC Name:	n.a.
Synonyms:	Lippiolide
Standard InCHIKey:	XVOHBMBYVJHVEX-PVXVMCPWSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-18(2)24-23-19-8-9-21-28(7,27(19,6)13-12-26(23,5)16-22(31)34-24)11-10-20-25(3,4)30(32)15-14-29(20,21)17-33-30/h19-21,23-24,32H,1,8-17H2,2-7H3/t19-,20+,21+,23+,24+,26+,27-,28-,29-,30-/m1/s1
SMILES:	CC(=C)C1C2C3CCC4C(C3(CCC2(CC(=O)O1)C)C)(CCC5C46CCC(C5(C)C)(OC6)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641870
PubChem CID:	50908706
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO25772	Lippia mexicana	Species	Verbenaceae	Eukaryota	n.a.	leaf	n.a.	PMID[20942442]
NPO25772	Lippia mexicana	Species	Verbenaceae	Eukaryota	n.a.	stem	n.a.	PMID[20942442]
NPO25772	Lippia mexicana	Species	Verbenaceae	Eukaryota	n.a.	flower	n.a.	PMID[20942442]
NPO25772	Lippia mexicana	Species	Verbenaceae	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
IC50	1
Others	2

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	74.9	%	PMID[534217]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	730.0	nM	PMID[534217]
NPT32	Organism	Mus musculus	Mus musculus	Ratio IC50	=	3.0	n.a.	PMID[534217]

☑ 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 NPC317573 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	258
0.1-0.2	1889
0.2-0.3	5467
0.3-0.4	12944
0.4-0.5	9949
0.5-0.6	5807
0.6-0.7	4259
0.7-0.8	2003
0.8-0.85	107
0.85-0.9	13
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8817	High Similarity	NPC475061
0.8723	High Similarity	NPC474963
0.8515	High Similarity	NPC475570
0.8478	Intermediate Similarity	NPC476932
0.8469	Intermediate Similarity	NPC473576
0.8469	Intermediate Similarity	NPC475156
0.8454	Intermediate Similarity	NPC470425
0.8431	Intermediate Similarity	NPC473483
0.837	Intermediate Similarity	NPC187545
0.8367	Intermediate Similarity	NPC58942
0.8367	Intermediate Similarity	NPC260149
0.8333	Intermediate Similarity	NPC303863
0.8333	Intermediate Similarity	NPC91010
0.8333	Intermediate Similarity	NPC469982
0.8265	Intermediate Similarity	NPC158347
0.8265	Intermediate Similarity	NPC189880
0.8247	Intermediate Similarity	NPC473240
0.8247	Intermediate Similarity	NPC474727
0.8229	Intermediate Similarity	NPC244356
0.8229	Intermediate Similarity	NPC224060
0.8229	Intermediate Similarity	NPC199543
0.8211	Intermediate Similarity	NPC113989
0.8211	Intermediate Similarity	NPC120840
0.8211	Intermediate Similarity	NPC474728
0.8191	Intermediate Similarity	NPC4309
0.819	Intermediate Similarity	NPC270586
0.8182	Intermediate Similarity	NPC475876
0.8163	Intermediate Similarity	NPC476318
0.8163	Intermediate Similarity	NPC476327
0.8125	Intermediate Similarity	NPC60755
0.8125	Intermediate Similarity	NPC470590
0.8125	Intermediate Similarity	NPC285184
0.8125	Intermediate Similarity	NPC77099
0.8125	Intermediate Similarity	NPC198054
0.8119	Intermediate Similarity	NPC476769
0.8119	Intermediate Similarity	NPC170615
0.8105	Intermediate Similarity	NPC30522
0.8085	Intermediate Similarity	NPC33768
0.8081	Intermediate Similarity	NPC476878
0.8081	Intermediate Similarity	NPC476879
0.8061	Intermediate Similarity	NPC470229
0.8061	Intermediate Similarity	NPC98639
0.8043	Intermediate Similarity	NPC471037
0.8041	Intermediate Similarity	NPC169343
0.8041	Intermediate Similarity	NPC86368
0.8039	Intermediate Similarity	NPC225238
0.8039	Intermediate Similarity	NPC139347
0.8021	Intermediate Similarity	NPC198818
0.8	Intermediate Similarity	NPC473844
0.8	Intermediate Similarity	NPC246708
0.8	Intermediate Similarity	NPC40552
0.8	Intermediate Similarity	NPC52169
0.8	Intermediate Similarity	NPC51947
0.8	Intermediate Similarity	NPC16377
0.8	Intermediate Similarity	NPC182797
0.8	Intermediate Similarity	NPC471250
0.7982	Intermediate Similarity	NPC473405
0.798	Intermediate Similarity	NPC329910
0.798	Intermediate Similarity	NPC219353
0.798	Intermediate Similarity	NPC29410
0.798	Intermediate Similarity	NPC200054
0.7979	Intermediate Similarity	NPC12774
0.7979	Intermediate Similarity	NPC2783
0.7979	Intermediate Similarity	NPC472505
0.7963	Intermediate Similarity	NPC110861
0.7961	Intermediate Similarity	NPC202793
0.7959	Intermediate Similarity	NPC78580
0.7959	Intermediate Similarity	NPC184006
0.7959	Intermediate Similarity	NPC23621
0.7959	Intermediate Similarity	NPC159365
0.7959	Intermediate Similarity	NPC474529
0.7959	Intermediate Similarity	NPC296164
0.7959	Intermediate Similarity	NPC475118
0.7959	Intermediate Similarity	NPC74751
0.7944	Intermediate Similarity	NPC12046
0.7944	Intermediate Similarity	NPC194951
0.7944	Intermediate Similarity	NPC476964
0.7938	Intermediate Similarity	NPC160506
0.7938	Intermediate Similarity	NPC471901
0.7938	Intermediate Similarity	NPC475708
0.7925	Intermediate Similarity	NPC270667
0.7925	Intermediate Similarity	NPC472666
0.7925	Intermediate Similarity	NPC279554
0.7925	Intermediate Similarity	NPC127056
0.7925	Intermediate Similarity	NPC56713
0.7925	Intermediate Similarity	NPC136877
0.7925	Intermediate Similarity	NPC475296
0.7925	Intermediate Similarity	NPC29069
0.7925	Intermediate Similarity	NPC90856
0.7925	Intermediate Similarity	NPC59804
0.7925	Intermediate Similarity	NPC474589
0.7925	Intermediate Similarity	NPC164194
0.7925	Intermediate Similarity	NPC174679
0.7921	Intermediate Similarity	NPC471413
0.7921	Intermediate Similarity	NPC476767
0.7917	Intermediate Similarity	NPC127689
0.7917	Intermediate Similarity	NPC59263
0.7917	Intermediate Similarity	NPC121798
0.7917	Intermediate Similarity	NPC234346
0.7917	Intermediate Similarity	NPC64872
0.7917	Intermediate Similarity	NPC470588
0.7917	Intermediate Similarity	NPC274330
0.7917	Intermediate Similarity	NPC130520
0.7917	Intermediate Similarity	NPC263393
0.7917	Intermediate Similarity	NPC225585
0.7917	Intermediate Similarity	NPC143232
0.7917	Intermediate Similarity	NPC293048
0.7917	Intermediate Similarity	NPC270768
0.7917	Intermediate Similarity	NPC290972
0.7917	Intermediate Similarity	NPC25906
0.7917	Intermediate Similarity	NPC61543
0.7917	Intermediate Similarity	NPC198664
0.7909	Intermediate Similarity	NPC471548
0.7905	Intermediate Similarity	NPC275539
0.7905	Intermediate Similarity	NPC189075
0.7905	Intermediate Similarity	NPC88744
0.79	Intermediate Similarity	NPC97867
0.79	Intermediate Similarity	NPC473456
0.7895	Intermediate Similarity	NPC46912
0.7895	Intermediate Similarity	NPC18064
0.7895	Intermediate Similarity	NPC51700
0.7895	Intermediate Similarity	NPC130577
0.7895	Intermediate Similarity	NPC242468
0.7895	Intermediate Similarity	NPC68160
0.7895	Intermediate Similarity	NPC307426
0.7895	Intermediate Similarity	NPC88716
0.7895	Intermediate Similarity	NPC162107
0.7895	Intermediate Similarity	NPC293564
0.7895	Intermediate Similarity	NPC98442
0.7895	Intermediate Similarity	NPC142415
0.7895	Intermediate Similarity	NPC264005
0.7895	Intermediate Similarity	NPC102683
0.7895	Intermediate Similarity	NPC269360
0.7895	Intermediate Similarity	NPC171203
0.789	Intermediate Similarity	NPC44170
0.789	Intermediate Similarity	NPC268954
0.7885	Intermediate Similarity	NPC28791
0.7885	Intermediate Similarity	NPC475611
0.7885	Intermediate Similarity	NPC295366
0.7879	Intermediate Similarity	NPC470232
0.7879	Intermediate Similarity	NPC139570
0.7879	Intermediate Similarity	NPC23241
0.7879	Intermediate Similarity	NPC195715
0.7872	Intermediate Similarity	NPC294438
0.7872	Intermediate Similarity	NPC98270
0.7872	Intermediate Similarity	NPC264317
0.787	Intermediate Similarity	NPC157441
0.7864	Intermediate Similarity	NPC471208
0.7857	Intermediate Similarity	NPC294263
0.7857	Intermediate Similarity	NPC291373
0.7857	Intermediate Similarity	NPC307335
0.7857	Intermediate Similarity	NPC295643
0.7857	Intermediate Similarity	NPC214756
0.7857	Intermediate Similarity	NPC473690
0.7857	Intermediate Similarity	NPC287118
0.7857	Intermediate Similarity	NPC136313
0.7857	Intermediate Similarity	NPC49776
0.7857	Intermediate Similarity	NPC74855
0.7857	Intermediate Similarity	NPC272075
0.7857	Intermediate Similarity	NPC63118
0.7857	Intermediate Similarity	NPC471902
0.7857	Intermediate Similarity	NPC474436
0.785	Intermediate Similarity	NPC179434
0.785	Intermediate Similarity	NPC30397
0.785	Intermediate Similarity	NPC470311
0.785	Intermediate Similarity	NPC1876
0.785	Intermediate Similarity	NPC91838
0.785	Intermediate Similarity	NPC473481
0.785	Intermediate Similarity	NPC471251
0.785	Intermediate Similarity	NPC11035
0.785	Intermediate Similarity	NPC164419
0.785	Intermediate Similarity	NPC240734
0.785	Intermediate Similarity	NPC211798
0.785	Intermediate Similarity	NPC108748
0.785	Intermediate Similarity	NPC204392
0.785	Intermediate Similarity	NPC297208
0.785	Intermediate Similarity	NPC275668
0.785	Intermediate Similarity	NPC235841
0.7843	Intermediate Similarity	NPC14634
0.7843	Intermediate Similarity	NPC235142
0.7843	Intermediate Similarity	NPC471412
0.7843	Intermediate Similarity	NPC253886
0.7843	Intermediate Similarity	NPC476888
0.7843	Intermediate Similarity	NPC93744
0.7843	Intermediate Similarity	NPC121218
0.7843	Intermediate Similarity	NPC75941
0.7838	Intermediate Similarity	NPC122971
0.7835	Intermediate Similarity	NPC477872
0.7835	Intermediate Similarity	NPC7260
0.7835	Intermediate Similarity	NPC273621
0.7835	Intermediate Similarity	NPC111110
0.7835	Intermediate Similarity	NPC126369
0.7835	Intermediate Similarity	NPC227467
0.7835	Intermediate Similarity	NPC210037
0.7835	Intermediate Similarity	NPC470589
0.7835	Intermediate Similarity	NPC290614
0.7835	Intermediate Similarity	NPC291028
0.7835	Intermediate Similarity	NPC130278
0.7835	Intermediate Similarity	NPC120968
0.7835	Intermediate Similarity	NPC18872

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 NPC317573 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	2258
0.2-0.3	3793
0.3-0.4	1902
0.4-0.5	562
0.5-0.6	249
0.6-0.7	119
0.7-0.8	19
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
0.7959	Intermediate Similarity	NPD7748	Approved
0.7938	Intermediate Similarity	NPD8035	Phase 2
0.7938	Intermediate Similarity	NPD8034	Phase 2
0.7872	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD8133	Approved
0.7755	Intermediate Similarity	NPD7515	Phase 2
0.7723	Intermediate Similarity	NPD7902	Approved
0.7647	Intermediate Similarity	NPD7638	Approved
0.7573	Intermediate Similarity	NPD7639	Approved
0.7573	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7900	Approved
0.7426	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD8328	Phase 3
0.7407	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7507	Approved
0.7182	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6697	Approved
0.7128	Intermediate Similarity	NPD6115	Approved
0.7128	Intermediate Similarity	NPD6118	Approved
0.7128	Intermediate Similarity	NPD6114	Approved
0.7107	Intermediate Similarity	NPD7319	Approved
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.7091	Intermediate Similarity	NPD6686	Approved
0.7	Intermediate Similarity	NPD3573	Approved
0.699	Remote Similarity	NPD6399	Phase 3
0.6915	Remote Similarity	NPD6117	Approved
0.6909	Remote Similarity	NPD6675	Approved
0.6909	Remote Similarity	NPD7128	Approved
0.6909	Remote Similarity	NPD5739	Approved
0.6909	Remote Similarity	NPD6402	Approved
0.6893	Remote Similarity	NPD6411	Approved
0.6875	Remote Similarity	NPD7645	Phase 2
0.6864	Remote Similarity	NPD8294	Approved
0.6864	Remote Similarity	NPD8377	Approved
0.6863	Remote Similarity	NPD5328	Approved
0.6842	Remote Similarity	NPD6116	Phase 1
0.6842	Remote Similarity	NPD6882	Approved
0.6809	Remote Similarity	NPD3703	Phase 2
0.6807	Remote Similarity	NPD8335	Approved
0.6807	Remote Similarity	NPD8379	Approved
0.6807	Remote Similarity	NPD8296	Approved
0.6807	Remote Similarity	NPD8378	Approved
0.6807	Remote Similarity	NPD8033	Approved
0.6807	Remote Similarity	NPD8380	Approved
0.6786	Remote Similarity	NPD7320	Approved
0.6786	Remote Similarity	NPD6899	Approved
0.6786	Remote Similarity	NPD6881	Approved
0.6765	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6079	Approved
0.6726	Remote Similarity	NPD6373	Approved
0.6726	Remote Similarity	NPD6372	Approved
0.6726	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6101	Approved
0.6696	Remote Similarity	NPD6412	Phase 2
0.6696	Remote Similarity	NPD5697	Approved
0.6696	Remote Similarity	NPD5701	Approved
0.6695	Remote Similarity	NPD7328	Approved
0.6695	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.6639	Remote Similarity	NPD7516	Approved
0.6637	Remote Similarity	NPD6011	Approved
0.6613	Remote Similarity	NPD7736	Approved
0.661	Remote Similarity	NPD7115	Discovery
0.661	Remote Similarity	NPD6009	Approved
0.6609	Remote Similarity	NPD6847	Approved
0.6609	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6869	Approved
0.6609	Remote Similarity	NPD6650	Approved
0.6609	Remote Similarity	NPD6649	Approved
0.6609	Remote Similarity	NPD6617	Approved
0.6609	Remote Similarity	NPD8130	Phase 1
0.6607	Remote Similarity	NPD6008	Approved
0.6579	Remote Similarity	NPD6013	Approved
0.6579	Remote Similarity	NPD6014	Approved
0.6579	Remote Similarity	NPD6012	Approved
0.6569	Remote Similarity	NPD7146	Approved
0.6569	Remote Similarity	NPD6684	Approved
0.6569	Remote Similarity	NPD6409	Approved
0.6569	Remote Similarity	NPD3618	Phase 1
0.6569	Remote Similarity	NPD5330	Approved
0.6569	Remote Similarity	NPD7521	Approved
0.6569	Remote Similarity	NPD7334	Approved
0.6552	Remote Similarity	NPD8297	Approved
0.6538	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4786	Approved
0.6514	Remote Similarity	NPD4225	Approved
0.6504	Remote Similarity	NPD7492	Approved
0.65	Remote Similarity	NPD3667	Approved
0.6496	Remote Similarity	NPD4632	Approved
0.6481	Remote Similarity	NPD5222	Approved
0.6481	Remote Similarity	NPD5221	Approved
0.6481	Remote Similarity	NPD4697	Phase 3
0.6481	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD3702	Approved
0.6452	Remote Similarity	NPD6616	Approved
0.6446	Remote Similarity	NPD6059	Approved
0.6446	Remote Similarity	NPD6054	Approved
0.6442	Remote Similarity	NPD6672	Approved
0.6442	Remote Similarity	NPD6903	Approved
0.6442	Remote Similarity	NPD5737	Approved
0.6436	Remote Similarity	NPD4788	Approved
0.6422	Remote Similarity	NPD5173	Approved
0.6422	Remote Similarity	NPD4755	Approved
0.6422	Remote Similarity	NPD6083	Phase 2
0.6422	Remote Similarity	NPD6084	Phase 2
0.6404	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8293	Discontinued
0.64	Remote Similarity	NPD7078	Approved
0.6393	Remote Similarity	NPD7503	Approved
0.6387	Remote Similarity	NPD6868	Approved
0.6341	Remote Similarity	NPD6370	Approved
0.6339	Remote Similarity	NPD5211	Phase 2
0.633	Remote Similarity	NPD7614	Phase 1
0.6325	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5777	Approved
0.6316	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6319	Approved
0.6311	Remote Similarity	NPD1694	Approved
0.6306	Remote Similarity	NPD5286	Approved
0.6306	Remote Similarity	NPD5285	Approved
0.6306	Remote Similarity	NPD4700	Approved
0.6306	Remote Similarity	NPD4696	Approved
0.63	Remote Similarity	NPD7525	Registered
0.629	Remote Similarity	NPD7604	Phase 2
0.6281	Remote Similarity	NPD6335	Approved
0.6277	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6053	Discontinued
0.6262	Remote Similarity	NPD5693	Phase 1
0.626	Remote Similarity	NPD6016	Approved
0.626	Remote Similarity	NPD5983	Phase 2
0.626	Remote Similarity	NPD6015	Approved
0.625	Remote Similarity	NPD6274	Approved
0.625	Remote Similarity	NPD5223	Approved
0.6239	Remote Similarity	NPD5695	Phase 3
0.6239	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD1779	Approved
0.6238	Remote Similarity	NPD1780	Approved
0.623	Remote Similarity	NPD7100	Approved
0.623	Remote Similarity	NPD7101	Approved
0.6228	Remote Similarity	NPD5141	Approved
0.6226	Remote Similarity	NPD6051	Approved
0.6216	Remote Similarity	NPD5696	Approved
0.6214	Remote Similarity	NPD3668	Phase 3
0.6214	Remote Similarity	NPD3665	Phase 1
0.6214	Remote Similarity	NPD3133	Approved
0.6214	Remote Similarity	NPD3666	Approved
0.621	Remote Similarity	NPD5988	Approved
0.6204	Remote Similarity	NPD4202	Approved
0.6198	Remote Similarity	NPD6317	Approved
0.6195	Remote Similarity	NPD5226	Approved
0.6195	Remote Similarity	NPD5225	Approved
0.6195	Remote Similarity	NPD5224	Approved
0.6195	Remote Similarity	NPD4633	Approved
0.619	Remote Similarity	NPD6336	Discontinued
0.6182	Remote Similarity	NPD7839	Suspended
0.6182	Remote Similarity	NPD7732	Phase 3
0.6168	Remote Similarity	NPD46	Approved
0.6168	Remote Similarity	NPD6698	Approved
0.6148	Remote Similarity	NPD6313	Approved
0.6148	Remote Similarity	NPD6314	Approved
0.6146	Remote Similarity	NPD6081	Approved
0.6142	Remote Similarity	NPD8074	Phase 3
0.614	Remote Similarity	NPD5174	Approved
0.614	Remote Similarity	NPD5175	Approved
0.614	Remote Similarity	NPD4754	Approved
0.6139	Remote Similarity	NPD6928	Phase 2
0.6129	Remote Similarity	NPD6909	Approved
0.6129	Remote Similarity	NPD4224	Phase 2
0.6129	Remote Similarity	NPD6908	Approved
0.6117	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD3669	Approved
0.6111	Remote Similarity	NPD7637	Suspended
0.6102	Remote Similarity	NPD4634	Approved
0.6095	Remote Similarity	NPD6422	Discontinued
0.6095	Remote Similarity	NPD6098	Approved
0.6094	Remote Similarity	NPD6033	Approved
0.6075	Remote Similarity	NPD6080	Approved
0.6075	Remote Similarity	NPD6904	Approved
0.6075	Remote Similarity	NPD6673	Approved
0.6042	Remote Similarity	NPD4245	Approved
0.6042	Remote Similarity	NPD4244	Approved
0.6034	Remote Similarity	NPD4768	Approved
0.6034	Remote Similarity	NPD4767	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