NPASS Compound

Structure

NPC473635 OpenBabel07101718272D 41 46 0 0 1 0 0 0 0 0999 V2000 8.6257 -1.3567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2875 -2.8430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0025 1.2702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6720 1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6665 2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3386 -0.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6476 -1.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9785 -1.8920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0733 1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3604 0.0102 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 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 6.0003 -1.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0514 0.9612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3312 -2.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2593 1.9394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6913 -0.7330 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 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 31 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 2 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 16 2 0 0 0 0 16 28 1 0 0 0 0 17 33 2 0 0 0 0 17 38 1 0 0 0 0 18 34 2 0 0 0 0 18 39 1 0 0 0 0 19 25 1 0 0 0 0 19 29 1 6 0 0 0 20 25 1 0 0 0 0 20 30 1 6 0 0 0 21 29 1 6 0 0 0 21 31 1 0 0 0 0 22 30 1 0 0 0 0 22 35 2 0 0 0 0 23 32 1 6 0 0 0 23 38 1 0 0 0 0 24 31 1 1 0 0 0 24 40 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 0 0 0 0 26 39 1 0 0 0 0 27 32 1 0 0 0 0 27 41 1 0 0 0 0 28 36 2 0 0 0 0 28 40 1 0 0 0 0 30 32 1 0 0 0 0 31 37 1 0 0 0 0 32 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.28
Volume:	573.983
LogP:	3.468
LogD:	2.486
LogS:	-4.65
# Rotatable Bonds:	6
TPSA:	128.73
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.232
Synthetic Accessibility Score:	6.264
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.14
MDCK Permeability:	8.771420834818855e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.925
Plasma Protein Binding (PPB):	50.894256591796875%
Volume Distribution (VD):	0.865
Pgp-substrate:	48.33488082885742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.182
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.372
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.529
CYP3A4-substrate:	0.522

ADMET: Excretion

Clearance (CL):	3.863
Half-life (T1/2):	0.773

ADMET: Toxicity

hERG Blockers:	0.312
Human Hepatotoxicity (H-HT):	0.89
Drug-inuced Liver Injury (DILI):	0.392
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.053
Skin Sensitization:	0.507
Carcinogencity:	0.094
Eye Corrosion:	0.006
Eye Irritation:	0.014
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC473635

Natural Product ID:	NPC473635
*Common Name:**	IFQUEPTUVAUUGK-MAGBKWLRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IFQUEPTUVAUUGK-MAGBKWLRSA-N
Standard InCHI:	InChI=1S/C32H42O9/c1-15-14-24(40-28(36)16(15)2)31(7,37)21-9-8-19-25-20(12-13-29(19,21)5)30(6)22(35)10-11-23(38-17(3)33)32(30)27(41-32)26(25)39-18(4)34/h10-11,19-21,23-27,37H,8-9,12-14H2,1-7H3/t19-,20-,21-,23-,24+,25-,26+,27+,29-,30-,31+,32+/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@H]2[C@@H]3CC[C@@H]([C@@]3(C)CC[C@@H]2[C@@]2([C@]3([C@@H]1O3)[C@H](C=CC2=O)OC(=O)C)C)[C@]([C@H]1CC(=C(C(=O)O1)C)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447745
PubChem CID:	44567004
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

*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
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO27252	Iochroma australe	Species	Solanaceae	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
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	0.26	uM	PMID[564051]
NPT27	Others	Unspecified		IC50	=	330.0	nM	PMID[564051]
NPT2	Others	Unspecified		Ratio	=	1.3	n.a.	PMID[564051]

☑ 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 NPC473635 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	267
0.1-0.2	1472
0.2-0.3	4124
0.3-0.4	6934
0.4-0.5	11941
0.5-0.6	8274
0.6-0.7	6388
0.7-0.8	2821
0.8-0.85	326
0.85-0.9	106
0.9-0.95	33
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9739	High Similarity	NPC170538
0.9658	High Similarity	NPC293112
0.9655	High Similarity	NPC11895
0.9487	High Similarity	NPC469789
0.9407	High Similarity	NPC81736
0.9407	High Similarity	NPC172154
0.9402	High Similarity	NPC470265
0.9402	High Similarity	NPC23786
0.9316	High Similarity	NPC67569
0.9244	High Similarity	NPC8369
0.9231	High Similarity	NPC251226
0.9153	High Similarity	NPC159456
0.9153	High Similarity	NPC4021
0.9145	High Similarity	NPC475520
0.9098	High Similarity	NPC231529
0.9076	High Similarity	NPC269642
0.9068	High Similarity	NPC154491
0.9068	High Similarity	NPC268530
0.906	High Similarity	NPC50774
0.906	High Similarity	NPC709
0.8974	High Similarity	NPC20302
0.8974	High Similarity	NPC286528
0.8974	High Similarity	NPC140055
0.8974	High Similarity	NPC167606
0.8952	High Similarity	NPC231240
0.8943	High Similarity	NPC476966
0.8934	High Similarity	NPC287423
0.8926	High Similarity	NPC8374
0.8926	High Similarity	NPC469790
0.8908	High Similarity	NPC474370
0.8908	High Similarity	NPC476961
0.8898	High Similarity	NPC473720
0.888	High Similarity	NPC316915
0.8862	High Similarity	NPC473620
0.8852	High Similarity	NPC120994
0.8852	High Similarity	NPC203702
0.8843	High Similarity	NPC120724
0.8843	High Similarity	NPC204812
0.8833	High Similarity	NPC46570
0.8833	High Similarity	NPC310511
0.8824	High Similarity	NPC5292
0.8824	High Similarity	NPC42673
0.8824	High Similarity	NPC475041
0.8824	High Similarity	NPC476960
0.8824	High Similarity	NPC473203
0.8824	High Similarity	NPC473636
0.8824	High Similarity	NPC264954
0.8824	High Similarity	NPC77689
0.8814	High Similarity	NPC470492
0.8814	High Similarity	NPC55296
0.8814	High Similarity	NPC470493
0.8814	High Similarity	NPC183580
0.8814	High Similarity	NPC312824
0.8814	High Similarity	NPC469684
0.8803	High Similarity	NPC67259
0.8803	High Similarity	NPC147912
0.879	High Similarity	NPC473593
0.878	High Similarity	NPC42399
0.877	High Similarity	NPC3381
0.877	High Similarity	NPC32868
0.877	High Similarity	NPC241456
0.876	High Similarity	NPC88326
0.876	High Similarity	NPC153700
0.876	High Similarity	NPC107493
0.8739	High Similarity	NPC153440
0.8739	High Similarity	NPC284707
0.8729	High Similarity	NPC190286
0.8729	High Similarity	NPC270929
0.8718	High Similarity	NPC122056
0.871	High Similarity	NPC245094
0.8707	High Similarity	NPC474229
0.8689	High Similarity	NPC473979
0.8667	High Similarity	NPC472667
0.8667	High Similarity	NPC61520
0.8667	High Similarity	NPC230513
0.8667	High Similarity	NPC211093
0.8667	High Similarity	NPC473839
0.8655	High Similarity	NPC98249
0.8655	High Similarity	NPC476965
0.8655	High Similarity	NPC53396
0.8655	High Similarity	NPC58662
0.8655	High Similarity	NPC470959
0.8655	High Similarity	NPC134430
0.8651	High Similarity	NPC471855
0.8644	High Similarity	NPC238667
0.8644	High Similarity	NPC284915
0.864	High Similarity	NPC470880
0.8632	High Similarity	NPC269530
0.8629	High Similarity	NPC473253
0.8629	High Similarity	NPC470882
0.8621	High Similarity	NPC472215
0.8621	High Similarity	NPC473627
0.8621	High Similarity	NPC253906
0.8621	High Similarity	NPC472214
0.8618	High Similarity	NPC24651
0.8618	High Similarity	NPC470494
0.8595	High Similarity	NPC474585
0.8595	High Similarity	NPC79579
0.8583	High Similarity	NPC186525
0.8583	High Similarity	NPC257457
0.8583	High Similarity	NPC311554
0.8583	High Similarity	NPC329736
0.8571	High Similarity	NPC176840
0.8571	High Similarity	NPC173347
0.8559	High Similarity	NPC477126
0.8559	High Similarity	NPC25909
0.8547	High Similarity	NPC469655
0.8547	High Similarity	NPC469656
0.8547	High Similarity	NPC474846
0.8537	High Similarity	NPC265557
0.8537	High Similarity	NPC105926
0.8537	High Similarity	NPC67251
0.8537	High Similarity	NPC91693
0.8537	High Similarity	NPC18945
0.8537	High Similarity	NPC473802
0.8534	High Similarity	NPC469370
0.8534	High Similarity	NPC284828
0.8534	High Similarity	NPC5475
0.8534	High Similarity	NPC173905
0.8534	High Similarity	NPC472216
0.8512	High Similarity	NPC470186
0.8512	High Similarity	NPC305260
0.8512	High Similarity	NPC270850
0.8512	High Similarity	NPC473274
0.85	High Similarity	NPC475809
0.85	High Similarity	NPC239273
0.85	High Similarity	NPC474518
0.8492	Intermediate Similarity	NPC471407
0.848	Intermediate Similarity	NPC298841
0.848	Intermediate Similarity	NPC473265
0.8475	Intermediate Similarity	NPC236217
0.8468	Intermediate Similarity	NPC470922
0.8468	Intermediate Similarity	NPC473709
0.8468	Intermediate Similarity	NPC473919
0.8468	Intermediate Similarity	NPC476729
0.8468	Intermediate Similarity	NPC318135
0.8468	Intermediate Similarity	NPC473255
0.8455	Intermediate Similarity	NPC312833
0.8443	Intermediate Similarity	NPC476962
0.8443	Intermediate Similarity	NPC143755
0.8435	Intermediate Similarity	NPC103088
0.8435	Intermediate Similarity	NPC470975
0.8435	Intermediate Similarity	NPC470979
0.843	Intermediate Similarity	NPC146280
0.843	Intermediate Similarity	NPC251310
0.843	Intermediate Similarity	NPC124676
0.8417	Intermediate Similarity	NPC64318
0.8417	Intermediate Similarity	NPC470075
0.8413	Intermediate Similarity	NPC311534
0.8403	Intermediate Similarity	NPC317210
0.8403	Intermediate Similarity	NPC471204
0.8403	Intermediate Similarity	NPC962
0.8403	Intermediate Similarity	NPC250109
0.84	Intermediate Similarity	NPC471939
0.839	Intermediate Similarity	NPC470960
0.8387	Intermediate Similarity	NPC6193
0.8374	Intermediate Similarity	NPC102822
0.8374	Intermediate Similarity	NPC473256
0.8374	Intermediate Similarity	NPC470779
0.8374	Intermediate Similarity	NPC204731
0.8374	Intermediate Similarity	NPC477046
0.8374	Intermediate Similarity	NPC470878
0.8372	Intermediate Similarity	NPC476823
0.8362	Intermediate Similarity	NPC180744
0.8361	Intermediate Similarity	NPC475775
0.8361	Intermediate Similarity	NPC476529
0.8359	Intermediate Similarity	NPC34963
0.8359	Intermediate Similarity	NPC476193
0.8347	Intermediate Similarity	NPC97908
0.8347	Intermediate Similarity	NPC287343
0.8347	Intermediate Similarity	NPC243065
0.8347	Intermediate Similarity	NPC122033
0.8347	Intermediate Similarity	NPC478204
0.8347	Intermediate Similarity	NPC473968
0.8347	Intermediate Similarity	NPC474654
0.8347	Intermediate Similarity	NPC471854
0.8347	Intermediate Similarity	NPC284068
0.8347	Intermediate Similarity	NPC13713
0.8347	Intermediate Similarity	NPC473590
0.8347	Intermediate Similarity	NPC470854
0.8346	Intermediate Similarity	NPC35109
0.8346	Intermediate Similarity	NPC221414
0.8333	Intermediate Similarity	NPC471940
0.8333	Intermediate Similarity	NPC474181
0.8333	Intermediate Similarity	NPC243354
0.8333	Intermediate Similarity	NPC470953
0.8319	Intermediate Similarity	NPC277769
0.8319	Intermediate Similarity	NPC152117
0.8319	Intermediate Similarity	NPC234042
0.8319	Intermediate Similarity	NPC476163
0.8306	Intermediate Similarity	NPC162009
0.8306	Intermediate Similarity	NPC222688
0.8306	Intermediate Similarity	NPC257017
0.8305	Intermediate Similarity	NPC474567
0.8305	Intermediate Similarity	NPC37116
0.8295	Intermediate Similarity	NPC58029
0.8295	Intermediate Similarity	NPC469673
0.8293	Intermediate Similarity	NPC107338
0.8293	Intermediate Similarity	NPC109607
0.8291	Intermediate Similarity	NPC472218

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 NPC473635 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	1614
0.2-0.3	3645
0.3-0.4	2342
0.4-0.5	737
0.5-0.6	313
0.6-0.7	163
0.7-0.8	93
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8974	High Similarity	NPD7115	Discovery
0.8145	Intermediate Similarity	NPD6319	Approved
0.8062	Intermediate Similarity	NPD7319	Approved
0.8017	Intermediate Similarity	NPD8297	Approved
0.8	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD7736	Approved
0.7833	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7507	Approved
0.7815	Intermediate Similarity	NPD6008	Approved
0.7805	Intermediate Similarity	NPD4632	Approved
0.7787	Intermediate Similarity	NPD6650	Approved
0.7787	Intermediate Similarity	NPD6649	Approved
0.7752	Intermediate Similarity	NPD7492	Approved
0.775	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD6054	Approved
0.7692	Intermediate Similarity	NPD6616	Approved
0.7686	Intermediate Similarity	NPD6899	Approved
0.7686	Intermediate Similarity	NPD6881	Approved
0.7642	Intermediate Similarity	NPD8130	Phase 1
0.7634	Intermediate Similarity	NPD7078	Approved
0.7623	Intermediate Similarity	NPD6372	Approved
0.7623	Intermediate Similarity	NPD6373	Approved
0.7603	Intermediate Similarity	NPD5697	Approved
0.7597	Intermediate Similarity	NPD6370	Approved
0.7581	Intermediate Similarity	NPD6882	Approved
0.7561	Intermediate Similarity	NPD7102	Approved
0.7561	Intermediate Similarity	NPD4634	Approved
0.7561	Intermediate Similarity	NPD7290	Approved
0.7561	Intermediate Similarity	NPD6883	Approved
0.7538	Intermediate Similarity	NPD8328	Phase 3
0.7538	Intermediate Similarity	NPD7604	Phase 2
0.7521	Intermediate Similarity	NPD7128	Approved
0.7521	Intermediate Similarity	NPD6402	Approved
0.7521	Intermediate Similarity	NPD5739	Approved
0.7521	Intermediate Similarity	NPD6675	Approved
0.7519	Intermediate Similarity	NPD8513	Phase 3
0.7519	Intermediate Similarity	NPD6015	Approved
0.7519	Intermediate Similarity	NPD7503	Approved
0.7519	Intermediate Similarity	NPD6016	Approved
0.75	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6617	Approved
0.75	Intermediate Similarity	NPD8293	Discontinued
0.748	Intermediate Similarity	NPD6013	Approved
0.748	Intermediate Similarity	NPD6012	Approved
0.748	Intermediate Similarity	NPD6014	Approved
0.748	Intermediate Similarity	NPD6009	Approved
0.7462	Intermediate Similarity	NPD5988	Approved
0.7458	Intermediate Similarity	NPD7638	Approved
0.7458	Intermediate Similarity	NPD4225	Approved
0.7442	Intermediate Similarity	NPD6059	Approved
0.7422	Intermediate Similarity	NPD7327	Approved
0.7422	Intermediate Similarity	NPD7328	Approved
0.7398	Intermediate Similarity	NPD6011	Approved
0.7398	Intermediate Similarity	NPD6686	Approved
0.7398	Intermediate Similarity	NPD7320	Approved
0.7395	Intermediate Similarity	NPD7639	Approved
0.7395	Intermediate Similarity	NPD7640	Approved
0.7385	Intermediate Similarity	NPD8379	Approved
0.7385	Intermediate Similarity	NPD8335	Approved
0.7385	Intermediate Similarity	NPD8517	Approved
0.7385	Intermediate Similarity	NPD5983	Phase 2
0.7385	Intermediate Similarity	NPD8515	Approved
0.7385	Intermediate Similarity	NPD8033	Approved
0.7385	Intermediate Similarity	NPD8380	Approved
0.7385	Intermediate Similarity	NPD8296	Approved
0.7385	Intermediate Similarity	NPD8378	Approved
0.7385	Intermediate Similarity	NPD8516	Approved
0.7333	Intermediate Similarity	NPD5344	Discontinued
0.7328	Intermediate Similarity	NPD6399	Phase 3
0.7317	Intermediate Similarity	NPD5701	Approved
0.7308	Intermediate Similarity	NPD8377	Approved
0.7308	Intermediate Similarity	NPD8294	Approved
0.7302	Intermediate Similarity	NPD6053	Discontinued
0.7293	Intermediate Similarity	NPD6336	Discontinued
0.728	Intermediate Similarity	NPD6371	Approved
0.7273	Intermediate Similarity	NPD5211	Phase 2
0.7252	Intermediate Similarity	NPD6921	Approved
0.725	Intermediate Similarity	NPD5286	Approved
0.725	Intermediate Similarity	NPD4696	Approved
0.725	Intermediate Similarity	NPD5285	Approved
0.7241	Intermediate Similarity	NPD6079	Approved
0.7227	Intermediate Similarity	NPD7902	Approved
0.7209	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6412	Phase 2
0.7177	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5141	Approved
0.7153	Intermediate Similarity	NPD7260	Phase 2
0.7131	Intermediate Similarity	NPD5224	Approved
0.7131	Intermediate Similarity	NPD5226	Approved
0.7131	Intermediate Similarity	NPD5225	Approved
0.7131	Intermediate Similarity	NPD4633	Approved
0.7119	Intermediate Similarity	NPD7748	Approved
0.7109	Intermediate Similarity	NPD8133	Approved
0.7107	Intermediate Similarity	NPD6648	Approved
0.7099	Intermediate Similarity	NPD7101	Approved
0.7099	Intermediate Similarity	NPD7100	Approved
0.7087	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4755	Approved
0.7073	Intermediate Similarity	NPD5174	Approved
0.7073	Intermediate Similarity	NPD5175	Approved
0.7069	Intermediate Similarity	NPD5328	Approved
0.7049	Intermediate Similarity	NPD5223	Approved
0.7023	Intermediate Similarity	NPD6335	Approved
0.7009	Intermediate Similarity	NPD6698	Approved
0.7009	Intermediate Similarity	NPD46	Approved
0.7	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5221	Approved
0.7	Intermediate Similarity	NPD6274	Approved
0.7	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD8074	Phase 3
0.6984	Remote Similarity	NPD4730	Approved
0.6984	Remote Similarity	NPD4729	Approved
0.6975	Remote Similarity	NPD7900	Approved
0.6975	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD4700	Approved
0.6949	Remote Similarity	NPD8034	Phase 2
0.6949	Remote Similarity	NPD8035	Phase 2
0.6947	Remote Similarity	NPD6317	Approved
0.6942	Remote Similarity	NPD5173	Approved
0.6942	Remote Similarity	NPD6084	Phase 2
0.6942	Remote Similarity	NPD6083	Phase 2
0.6934	Remote Similarity	NPD6033	Approved
0.6917	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3573	Approved
0.6894	Remote Similarity	NPD6314	Approved
0.6894	Remote Similarity	NPD6313	Approved
0.6885	Remote Similarity	NPD5696	Approved
0.6875	Remote Similarity	NPD5250	Approved
0.6875	Remote Similarity	NPD5248	Approved
0.6875	Remote Similarity	NPD5251	Approved
0.6875	Remote Similarity	NPD5249	Phase 3
0.6875	Remote Similarity	NPD5247	Approved
0.687	Remote Similarity	NPD6868	Approved
0.6866	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7838	Discovery
0.686	Remote Similarity	NPD4697	Phase 3
0.6855	Remote Similarity	NPD7632	Discontinued
0.6825	Remote Similarity	NPD4767	Approved
0.6825	Remote Similarity	NPD4768	Approved
0.6822	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3618	Phase 1
0.681	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7983	Approved
0.6807	Remote Similarity	NPD7515	Phase 2
0.6807	Remote Similarity	NPD7637	Suspended
0.6777	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5695	Phase 3
0.675	Remote Similarity	NPD5778	Approved
0.675	Remote Similarity	NPD4202	Approved
0.675	Remote Similarity	NPD5779	Approved
0.6741	Remote Similarity	NPD6908	Approved
0.6741	Remote Similarity	NPD6909	Approved
0.6738	Remote Similarity	NPD6845	Suspended
0.6724	Remote Similarity	NPD1694	Approved
0.6723	Remote Similarity	NPD5785	Approved
0.6719	Remote Similarity	NPD5128	Approved
0.6695	Remote Similarity	NPD5737	Approved
0.6695	Remote Similarity	NPD6672	Approved
0.6695	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5217	Approved
0.6692	Remote Similarity	NPD5215	Approved
0.6692	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6639	Remote Similarity	NPD4629	Approved
0.6639	Remote Similarity	NPD5210	Approved
0.6638	Remote Similarity	NPD4786	Approved
0.6615	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5135	Approved
0.6615	Remote Similarity	NPD5169	Approved
0.6585	Remote Similarity	NPD7799	Discontinued
0.6565	Remote Similarity	NPD5127	Approved
0.6557	Remote Similarity	NPD6001	Approved
0.6555	Remote Similarity	NPD6903	Approved
0.6513	Remote Similarity	NPD7236	Approved
0.6508	Remote Similarity	NPD1700	Approved
0.6507	Remote Similarity	NPD6333	Approved
0.6507	Remote Similarity	NPD6334	Approved
0.6503	Remote Similarity	NPD8338	Approved
0.65	Remote Similarity	NPD6080	Approved
0.65	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6673	Approved
0.65	Remote Similarity	NPD6101	Approved
0.65	Remote Similarity	NPD4753	Phase 2
0.65	Remote Similarity	NPD6904	Approved
0.648	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD5956	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