NPASS Compound

Structure

NPC148463 OpenBabel07101719252D 30 32 0 0 1 0 0 0 0 0999 V2000 -3.6950 -0.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4469 2.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4469 -1.9943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0224 1.7708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0224 1.7708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6901 0.7237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0447 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0447 0.6032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5224 -0.3016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1358 0.3335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4718 -0.6722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3261 1.1106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7531 0.2873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5185 2.9692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5185 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9277 -0.2772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4718 1.2753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8748 1.3612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8748 -0.7580 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.6032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4714 1.2468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3261 -0.5074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5224 0.9048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3762 3.9590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3762 -3.3558 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0821 2.0387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3288 -1.2632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7325 2.3510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7325 -1.7478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 23 1 0 0 0 0 9 24 1 0 0 0 0 10 17 2 0 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 25 2 0 0 0 0 14 29 1 0 0 0 0 15 26 2 0 0 0 0 15 30 1 0 0 0 0 16 10 1 1 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 29 1 6 0 0 0 19 22 1 0 0 0 0 19 30 1 1 0 0 0 20 23 1 0 0 0 0 20 24 1 6 0 0 0 21 27 2 0 0 0 0 22 24 1 0 0 0 0 22 28 2 0 0 0 0 24 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.22
Volume:	434.913
LogP:	3.333
LogD:	2.44
LogS:	-4.555
# Rotatable Bonds:	4
TPSA:	86.74
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.631
Synthetic Accessibility Score:	5.745
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.93
MDCK Permeability:	1.8537784853833728e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.017
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.886
30% Bioavailability (F30%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	91.02521514892578%
Volume Distribution (VD):	0.924
Pgp-substrate:	13.60300064086914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.226
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.553
CYP2C9-substrate:	0.21
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.708
CYP3A4-substrate:	0.485

ADMET: Excretion

Clearance (CL):	2.06
Half-life (T1/2):	0.777

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.068
Drug-inuced Liver Injury (DILI):	0.817
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.792
Maximum Recommended Daily Dose:	0.459
Skin Sensitization:	0.802
Carcinogencity:	0.383
Eye Corrosion:	0.237
Eye Irritation:	0.182
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC148463

Natural Product ID:	NPC148463
*Common Name:**	REDVWPQXGVFYQX-AYQBYMDZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	REDVWPQXGVFYQX-AYQBYMDZSA-N
Standard InCHI:	InChI=1S/C24H32O6/c1-13-16-10-17(21(13)27)18(29-14(2)25)12-20-23(4,5)8-7-9-24(20,6)22(28)19(11-16)30-15(3)26/h10,16,18-20H,1,7-9,11-12H2,2-6H3/t16-,18+,19-,20+,24+/m0/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H]2C(C)(C)CCC[C@@]2(C)C(=O)[C@H](C[C@@H]2C=C1C(=O)C2=C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456865
PubChem CID:	3010860
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0003677] Alpha-acyloxy carbonyl compounds [CHEMONTID:0003420] Alpha-acyloxy ketones

*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
NPO9759	Croton kongensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828479]
NPO9759	Croton kongensis	Species	Euphorbiaceae	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	3
MIC	1

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	3.2	ug.mL-1	PMID[510951]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	13.8	ug.mL-1	PMID[510951]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	25.0	ug.mL-1	PMID[510951]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	2.8	ug.mL-1	PMID[510951]

☑ 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 NPC148463 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	223
0.1-0.2	1364
0.2-0.3	5430
0.3-0.4	10612
0.4-0.5	12540
0.5-0.6	6983
0.6-0.7	4740
0.7-0.8	772
0.8-0.85	30
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.913	High Similarity	NPC184065
0.8791	High Similarity	NPC471818
0.871	High Similarity	NPC476596
0.8602	High Similarity	NPC476597
0.8602	High Similarity	NPC476598
0.8421	Intermediate Similarity	NPC474490
0.8421	Intermediate Similarity	NPC470978
0.8421	Intermediate Similarity	NPC470974
0.8352	Intermediate Similarity	NPC220478
0.8333	Intermediate Similarity	NPC149869
0.8333	Intermediate Similarity	NPC474359
0.8265	Intermediate Similarity	NPC306856
0.8242	Intermediate Similarity	NPC189311
0.8222	Intermediate Similarity	NPC222358
0.8191	Intermediate Similarity	NPC51486
0.8182	Intermediate Similarity	NPC476478
0.8172	Intermediate Similarity	NPC475906
0.8172	Intermediate Similarity	NPC469628
0.8172	Intermediate Similarity	NPC469631
0.8172	Intermediate Similarity	NPC469653
0.8172	Intermediate Similarity	NPC471047
0.8163	Intermediate Similarity	NPC54843
0.8132	Intermediate Similarity	NPC475100
0.8111	Intermediate Similarity	NPC200513
0.8105	Intermediate Similarity	NPC284185
0.8085	Intermediate Similarity	NPC280833
0.8022	Intermediate Similarity	NPC193198
0.8022	Intermediate Similarity	NPC474703
0.8	Intermediate Similarity	NPC8062
0.8	Intermediate Similarity	NPC253144
0.8	Intermediate Similarity	NPC472643
0.798	Intermediate Similarity	NPC222011
0.7979	Intermediate Similarity	NPC226863
0.7979	Intermediate Similarity	NPC475902
0.7978	Intermediate Similarity	NPC469620
0.7978	Intermediate Similarity	NPC469690
0.7957	Intermediate Similarity	NPC38576
0.7957	Intermediate Similarity	NPC279859
0.7938	Intermediate Similarity	NPC470697
0.7938	Intermediate Similarity	NPC53685
0.7938	Intermediate Similarity	NPC84893
0.7917	Intermediate Similarity	NPC150978
0.7917	Intermediate Similarity	NPC123177
0.7917	Intermediate Similarity	NPC177037
0.7917	Intermediate Similarity	NPC472814
0.7917	Intermediate Similarity	NPC74103
0.7917	Intermediate Similarity	NPC70595
0.7917	Intermediate Similarity	NPC219874
0.79	Intermediate Similarity	NPC117685
0.79	Intermediate Similarity	NPC174314
0.7895	Intermediate Similarity	NPC5509
0.7895	Intermediate Similarity	NPC284561
0.7879	Intermediate Similarity	NPC474343
0.7879	Intermediate Similarity	NPC2049
0.7879	Intermediate Similarity	NPC69385
0.7872	Intermediate Similarity	NPC478144
0.7865	Intermediate Similarity	NPC471220
0.7857	Intermediate Similarity	NPC209355
0.7849	Intermediate Similarity	NPC65661
0.7849	Intermediate Similarity	NPC110405
0.7843	Intermediate Similarity	NPC470954
0.7835	Intermediate Similarity	NPC115021
0.7826	Intermediate Similarity	NPC12283
0.7826	Intermediate Similarity	NPC474193
0.7822	Intermediate Similarity	NPC310981
0.7822	Intermediate Similarity	NPC475099
0.7822	Intermediate Similarity	NPC473384
0.7812	Intermediate Similarity	NPC152467
0.7812	Intermediate Similarity	NPC161638
0.7802	Intermediate Similarity	NPC282293
0.78	Intermediate Similarity	NPC471932
0.7788	Intermediate Similarity	NPC475294
0.7778	Intermediate Similarity	NPC118159
0.7778	Intermediate Similarity	NPC150646
0.7778	Intermediate Similarity	NPC242848
0.7767	Intermediate Similarity	NPC189616
0.7766	Intermediate Similarity	NPC261721
0.7755	Intermediate Similarity	NPC476415
0.7755	Intermediate Similarity	NPC469632
0.7742	Intermediate Similarity	NPC30486
0.7732	Intermediate Similarity	NPC472953
0.7732	Intermediate Similarity	NPC221282
0.7732	Intermediate Similarity	NPC473944
0.7732	Intermediate Similarity	NPC20713
0.7723	Intermediate Similarity	NPC471413
0.7723	Intermediate Similarity	NPC54705
0.7723	Intermediate Similarity	NPC472644
0.7723	Intermediate Similarity	NPC476933
0.7717	Intermediate Similarity	NPC85772
0.7714	Intermediate Similarity	NPC476479
0.7708	Intermediate Similarity	NPC174342
0.77	Intermediate Similarity	NPC53844
0.77	Intermediate Similarity	NPC84335
0.77	Intermediate Similarity	NPC38530
0.77	Intermediate Similarity	NPC475709
0.7692	Intermediate Similarity	NPC1679
0.7692	Intermediate Similarity	NPC223904
0.7692	Intermediate Similarity	NPC284365
0.7692	Intermediate Similarity	NPC123726
0.7684	Intermediate Similarity	NPC478145
0.7677	Intermediate Similarity	NPC295347
0.7677	Intermediate Similarity	NPC33473
0.7677	Intermediate Similarity	NPC473369
0.767	Intermediate Similarity	NPC472755
0.767	Intermediate Similarity	NPC19239
0.767	Intermediate Similarity	NPC474166
0.7667	Intermediate Similarity	NPC128276
0.766	Intermediate Similarity	NPC161957
0.766	Intermediate Similarity	NPC106416
0.766	Intermediate Similarity	NPC33570
0.766	Intermediate Similarity	NPC96621
0.766	Intermediate Similarity	NPC261380
0.766	Intermediate Similarity	NPC86316
0.766	Intermediate Similarity	NPC21471
0.7653	Intermediate Similarity	NPC271652
0.7653	Intermediate Similarity	NPC139692
0.7653	Intermediate Similarity	NPC79117
0.7653	Intermediate Similarity	NPC475657
0.7653	Intermediate Similarity	NPC475302
0.7647	Intermediate Similarity	NPC471412
0.7647	Intermediate Similarity	NPC472753
0.764	Intermediate Similarity	NPC27205
0.764	Intermediate Similarity	NPC473223
0.7634	Intermediate Similarity	NPC22611
0.7629	Intermediate Similarity	NPC212679
0.7629	Intermediate Similarity	NPC476369
0.7629	Intermediate Similarity	NPC469595
0.7629	Intermediate Similarity	NPC476437
0.7629	Intermediate Similarity	NPC220454
0.7624	Intermediate Similarity	NPC141191
0.7624	Intermediate Similarity	NPC316598
0.7624	Intermediate Similarity	NPC264378
0.7624	Intermediate Similarity	NPC176845
0.7619	Intermediate Similarity	NPC475510
0.7619	Intermediate Similarity	NPC475587
0.7609	Intermediate Similarity	NPC471325
0.7609	Intermediate Similarity	NPC286229
0.7609	Intermediate Similarity	NPC14203
0.7609	Intermediate Similarity	NPC40228
0.7609	Intermediate Similarity	NPC229584
0.7604	Intermediate Similarity	NPC215831
0.76	Intermediate Similarity	NPC29952
0.76	Intermediate Similarity	NPC185553
0.7596	Intermediate Similarity	NPC470297
0.7593	Intermediate Similarity	NPC264634
0.7582	Intermediate Similarity	NPC471299
0.7582	Intermediate Similarity	NPC28319
0.7582	Intermediate Similarity	NPC471740
0.7579	Intermediate Similarity	NPC70422
0.7579	Intermediate Similarity	NPC261253
0.7579	Intermediate Similarity	NPC469676
0.7579	Intermediate Similarity	NPC104961
0.7579	Intermediate Similarity	NPC472863
0.7579	Intermediate Similarity	NPC474045
0.7579	Intermediate Similarity	NPC202394
0.7579	Intermediate Similarity	NPC70555
0.7576	Intermediate Similarity	NPC477130
0.7576	Intermediate Similarity	NPC477129
0.7576	Intermediate Similarity	NPC476267
0.7573	Intermediate Similarity	NPC40918
0.7573	Intermediate Similarity	NPC308351
0.7573	Intermediate Similarity	NPC271266
0.7573	Intermediate Similarity	NPC162973
0.7573	Intermediate Similarity	NPC472754
0.7573	Intermediate Similarity	NPC80781
0.7556	Intermediate Similarity	NPC57744
0.7551	Intermediate Similarity	NPC218301
0.7551	Intermediate Similarity	NPC111114
0.7551	Intermediate Similarity	NPC300312
0.7551	Intermediate Similarity	NPC290651
0.7551	Intermediate Similarity	NPC261607
0.7549	Intermediate Similarity	NPC469551
0.7549	Intermediate Similarity	NPC476299
0.7549	Intermediate Similarity	NPC476274
0.7549	Intermediate Similarity	NPC471041
0.7549	Intermediate Similarity	NPC474012
0.7547	Intermediate Similarity	NPC220155
0.7547	Intermediate Similarity	NPC473939
0.7547	Intermediate Similarity	NPC473595
0.7528	Intermediate Similarity	NPC244166
0.7527	Intermediate Similarity	NPC178676
0.7526	Intermediate Similarity	NPC288699
0.7526	Intermediate Similarity	NPC73995
0.7526	Intermediate Similarity	NPC177141
0.7525	Intermediate Similarity	NPC476768
0.7525	Intermediate Similarity	NPC110937
0.7525	Intermediate Similarity	NPC253826
0.7525	Intermediate Similarity	NPC208094
0.7525	Intermediate Similarity	NPC169205
0.7524	Intermediate Similarity	NPC472645
0.7523	Intermediate Similarity	NPC159333
0.7523	Intermediate Similarity	NPC472929
0.7523	Intermediate Similarity	NPC472926
0.7523	Intermediate Similarity	NPC470120
0.75	Intermediate Similarity	NPC471365
0.75	Intermediate Similarity	NPC329345
0.75	Intermediate Similarity	NPC477228
0.75	Intermediate Similarity	NPC473283
0.75	Intermediate Similarity	NPC48803
0.75	Intermediate Similarity	NPC476600

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 NPC148463 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	1779
0.2-0.3	3878
0.3-0.4	2140
0.4-0.5	767
0.5-0.6	212
0.6-0.7	159
0.7-0.8	17
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
0.8111	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5737	Approved
0.7789	Intermediate Similarity	NPD6672	Approved
0.7551	Intermediate Similarity	NPD5693	Phase 1
0.7527	Intermediate Similarity	NPD5209	Approved
0.75	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD1694	Approved
0.7396	Intermediate Similarity	NPD7146	Approved
0.7396	Intermediate Similarity	NPD6684	Approved
0.7396	Intermediate Similarity	NPD7334	Approved
0.7396	Intermediate Similarity	NPD7521	Approved
0.7396	Intermediate Similarity	NPD6409	Approved
0.7396	Intermediate Similarity	NPD5330	Approved
0.7347	Intermediate Similarity	NPD6673	Approved
0.7347	Intermediate Similarity	NPD6080	Approved
0.7347	Intermediate Similarity	NPD6904	Approved
0.7273	Intermediate Similarity	NPD5785	Approved
0.7245	Intermediate Similarity	NPD6903	Approved
0.7245	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6881	Approved
0.7222	Intermediate Similarity	NPD6899	Approved
0.72	Intermediate Similarity	NPD6050	Approved
0.7196	Intermediate Similarity	NPD6675	Approved
0.7196	Intermediate Similarity	NPD6402	Approved
0.7196	Intermediate Similarity	NPD7128	Approved
0.7196	Intermediate Similarity	NPD5739	Approved
0.7184	Intermediate Similarity	NPD6083	Phase 2
0.7184	Intermediate Similarity	NPD6084	Phase 2
0.7157	Intermediate Similarity	NPD5695	Phase 3
0.713	Intermediate Similarity	NPD5697	Approved
0.7115	Intermediate Similarity	NPD4225	Approved
0.71	Intermediate Similarity	NPD5692	Phase 3
0.7091	Intermediate Similarity	NPD6883	Approved
0.7091	Intermediate Similarity	NPD7290	Approved
0.7091	Intermediate Similarity	NPD7102	Approved
0.7064	Intermediate Similarity	NPD7320	Approved
0.7064	Intermediate Similarity	NPD6011	Approved
0.7041	Intermediate Similarity	NPD6098	Approved
0.703	Intermediate Similarity	NPD5694	Approved
0.7027	Intermediate Similarity	NPD6847	Approved
0.7027	Intermediate Similarity	NPD6617	Approved
0.7027	Intermediate Similarity	NPD6650	Approved
0.7027	Intermediate Similarity	NPD6649	Approved
0.7027	Intermediate Similarity	NPD8130	Phase 1
0.7027	Intermediate Similarity	NPD6869	Approved
0.7	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD6013	Approved
0.7	Intermediate Similarity	NPD6012	Approved
0.7	Intermediate Similarity	NPD6373	Approved
0.6972	Remote Similarity	NPD5701	Approved
0.697	Remote Similarity	NPD3573	Approved
0.6964	Remote Similarity	NPD8297	Approved
0.6964	Remote Similarity	NPD6882	Approved
0.6957	Remote Similarity	NPD8039	Approved
0.6952	Remote Similarity	NPD7638	Approved
0.6952	Remote Similarity	NPD5696	Approved
0.6909	Remote Similarity	NPD6686	Approved
0.6893	Remote Similarity	NPD7748	Approved
0.6893	Remote Similarity	NPD7900	Approved
0.6893	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7640	Approved
0.6887	Remote Similarity	NPD7639	Approved
0.6875	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7115	Discovery
0.6863	Remote Similarity	NPD6411	Approved
0.6818	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5778	Approved
0.6796	Remote Similarity	NPD6399	Phase 3
0.6796	Remote Similarity	NPD5779	Approved
0.6786	Remote Similarity	NPD6371	Approved
0.6783	Remote Similarity	NPD6868	Approved
0.6771	Remote Similarity	NPD4695	Discontinued
0.6768	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5363	Approved
0.6762	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5221	Approved
0.6762	Remote Similarity	NPD5222	Approved
0.6731	Remote Similarity	NPD5282	Discontinued
0.67	Remote Similarity	NPD5786	Approved
0.67	Remote Similarity	NPD5279	Phase 3
0.6699	Remote Similarity	NPD7515	Phase 2
0.6699	Remote Similarity	NPD6079	Approved
0.6698	Remote Similarity	NPD5173	Approved
0.6698	Remote Similarity	NPD7902	Approved
0.6695	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD5654	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6638	Remote Similarity	NPD6274	Approved
0.6612	Remote Similarity	NPD7492	Approved
0.661	Remote Similarity	NPD7100	Approved
0.661	Remote Similarity	NPD7101	Approved
0.6606	Remote Similarity	NPD5211	Phase 2
0.6604	Remote Similarity	NPD4697	Phase 3
0.6581	Remote Similarity	NPD6317	Approved
0.6577	Remote Similarity	NPD6008	Approved
0.6574	Remote Similarity	NPD5286	Approved
0.6574	Remote Similarity	NPD5285	Approved
0.6574	Remote Similarity	NPD4696	Approved
0.6569	Remote Similarity	NPD5208	Approved
0.6562	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6616	Approved
0.6555	Remote Similarity	NPD6054	Approved
0.6542	Remote Similarity	NPD5959	Approved
0.6542	Remote Similarity	NPD4755	Approved
0.6525	Remote Similarity	NPD6314	Approved
0.6525	Remote Similarity	NPD6313	Approved
0.6518	Remote Similarity	NPD6614	Approved
0.6514	Remote Similarity	NPD5223	Approved
0.6505	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4753	Phase 2
0.6504	Remote Similarity	NPD7078	Approved
0.65	Remote Similarity	NPD3666	Approved
0.65	Remote Similarity	NPD3665	Phase 1
0.65	Remote Similarity	NPD3133	Approved
0.6486	Remote Similarity	NPD5141	Approved
0.6466	Remote Similarity	NPD4632	Approved
0.6465	Remote Similarity	NPD6435	Approved
0.6465	Remote Similarity	NPD4270	Approved
0.6465	Remote Similarity	NPD4269	Approved
0.6465	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5225	Approved
0.6455	Remote Similarity	NPD5226	Approved
0.6455	Remote Similarity	NPD5224	Approved
0.6455	Remote Similarity	NPD4633	Approved
0.6452	Remote Similarity	NPD7736	Approved
0.6449	Remote Similarity	NPD7732	Phase 3
0.6446	Remote Similarity	NPD6370	Approved
0.6442	Remote Similarity	NPD6698	Approved
0.6442	Remote Similarity	NPD46	Approved
0.6442	Remote Similarity	NPD5207	Approved
0.6441	Remote Similarity	NPD6009	Approved
0.6436	Remote Similarity	NPD5329	Approved
0.6422	Remote Similarity	NPD4700	Approved
0.6417	Remote Similarity	NPD6059	Approved
0.64	Remote Similarity	NPD5362	Discontinued
0.64	Remote Similarity	NPD7154	Phase 3
0.6396	Remote Similarity	NPD5175	Approved
0.6396	Remote Similarity	NPD5174	Approved
0.6393	Remote Similarity	NPD8328	Phase 3
0.6393	Remote Similarity	NPD7604	Phase 2
0.6381	Remote Similarity	NPD7637	Suspended
0.6379	Remote Similarity	NPD6053	Discontinued
0.6373	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5690	Phase 2
0.6373	Remote Similarity	NPD4519	Discontinued
0.6373	Remote Similarity	NPD3618	Phase 1
0.6373	Remote Similarity	NPD4623	Approved
0.6371	Remote Similarity	NPD8293	Discontinued
0.6364	Remote Similarity	NPD6909	Approved
0.6364	Remote Similarity	NPD6908	Approved
0.6364	Remote Similarity	NPD6016	Approved
0.6364	Remote Similarity	NPD5369	Approved
0.6364	Remote Similarity	NPD6015	Approved
0.6364	Remote Similarity	NPD5983	Phase 2
0.6355	Remote Similarity	NPD5210	Approved
0.6355	Remote Similarity	NPD4629	Approved
0.6348	Remote Similarity	NPD4634	Approved
0.6346	Remote Similarity	NPD1695	Approved
0.6337	Remote Similarity	NPD4197	Approved
0.6337	Remote Similarity	NPD4786	Approved
0.6337	Remote Similarity	NPD3668	Phase 3
0.6333	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5988	Approved
0.6306	Remote Similarity	NPD7632	Discontinued
0.63	Remote Similarity	NPD3667	Approved
0.6299	Remote Similarity	NPD7260	Phase 2
0.629	Remote Similarity	NPD6336	Discontinued
0.6289	Remote Similarity	NPD4756	Discovery
0.6275	Remote Similarity	NPD1696	Phase 3
0.627	Remote Similarity	NPD7319	Approved
0.6263	Remote Similarity	NPD4252	Approved
0.6263	Remote Similarity	NPD5368	Approved
0.6262	Remote Similarity	NPD6001	Approved
0.625	Remote Similarity	NPD4754	Approved
0.623	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5284	Approved
0.6226	Remote Similarity	NPD5281	Approved
0.6226	Remote Similarity	NPD7983	Approved
0.6224	Remote Similarity	NPD3617	Approved
0.6214	Remote Similarity	NPD4694	Approved
0.6214	Remote Similarity	NPD5280	Approved
0.6176	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4730	Approved
0.6174	Remote Similarity	NPD5168	Approved
0.6174	Remote Similarity	NPD5128	Approved
0.6174	Remote Similarity	NPD4729	Approved
0.617	Remote Similarity	NPD4691	Approved
0.616	Remote Similarity	NPD7507	Approved
0.6147	Remote Similarity	NPD7839	Suspended
0.6147	Remote Similarity	NPD7614	Phase 1
0.614	Remote Similarity	NPD4767	Approved
0.614	Remote Similarity	NPD4768	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