NPASS Compound

Structure

NPC469790 OpenBabel07101718202D 38 44 0 0 1 0 0 0 0 0999 V2000 -6.4325 -7.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7707 -5.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 -1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6502 -5.7382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -5.9190 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.1910 0.0000 C 0 0 0 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 -6.1235 -6.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7926 -5.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6369 -2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 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 -4.1369 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8363 -4.9680 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 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 -3.8090 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 -6.4836 -4.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8581 -4.7601 0.0000 C 0 0 2 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 -6.6369 -2.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1527 -3.6896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9071 -5.0691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 -4.2248 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 11 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 6 11 1 0 0 0 0 6 21 1 0 0 0 0 7 20 1 0 0 0 0 8 22 1 0 0 0 0 9 16 1 0 0 0 0 9 18 1 0 0 0 0 10 17 1 0 0 0 0 11 12 2 0 0 0 0 12 26 1 0 0 0 0 13 30 2 0 0 0 0 13 35 1 0 0 0 0 14 8 1 6 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 7 1 1 0 0 0 15 23 1 0 0 0 0 16 27 1 1 0 0 0 17 23 1 0 0 0 0 17 31 2 0 0 0 0 18 24 1 0 0 0 0 18 35 1 1 0 0 0 19 10 1 1 0 0 0 19 25 1 0 0 0 0 19 36 1 0 0 0 0 20 27 1 1 0 0 0 20 32 1 0 0 0 0 21 28 1 1 0 0 0 21 37 1 0 0 0 0 22 29 1 6 0 0 0 22 38 1 0 0 0 0 23 29 1 6 0 0 0 24 27 1 1 0 0 0 24 28 1 0 0 0 0 25 29 1 1 0 0 0 25 36 1 0 0 0 0 26 33 2 0 0 0 0 26 37 1 0 0 0 0 27 4 1 1 0 0 0 28 5 1 6 0 0 0 28 34 1 0 0 0 0 29 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.25
Volume:	518.811
LogP:	2.686
LogD:	1.909
LogS:	-4.459
# Rotatable Bonds:	4
TPSA:	135.19
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.318
Synthetic Accessibility Score:	6.552
Fsp3:	0.828
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:	-5.326
MDCK Permeability:	0.00011374992755008861
Pgp-inhibitor:	0.997
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.212
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.234
Plasma Protein Binding (PPB):	44.12303924560547%
Volume Distribution (VD):	0.797
Pgp-substrate:	46.4367790222168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.604
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.275
CYP3A4-substrate:	0.372

ADMET: Excretion

Clearance (CL):	5.552
Half-life (T1/2):	0.348

ADMET: Toxicity

hERG Blockers:	0.565
Human Hepatotoxicity (H-HT):	0.977
Drug-inuced Liver Injury (DILI):	0.78
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.592
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.269
Carcinogencity:	0.01
Eye Corrosion:	0.004
Eye Irritation:	0.009
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC469790

Natural Product ID:	NPC469790
*Common Name:**	FIMAYHJYWNSMFM-NNLREDAASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FIMAYHJYWNSMFM-NNLREDAASA-N
Standard InCHI:	InChI=1S/C29H38O9/c1-11-6-21(37-26(33)12(11)2)28(5,34)24-18(35-13(3)30)9-16-14-8-22-29(38-22)23(17(31)10-19-25(29)36-19)15(14)7-20(32)27(16,24)4/h14-16,18-25,32,34H,6-10H2,1-5H3/t14-,15+,16+,18+,19+,20-,21-,22-,23+,24+,25+,27-,28+,29-/m1/s1
SMILES:	CC1=C(C(=O)OC(C1)C(C)(C2C(CC3C2(C(CC4C3CC5C6(C4C(=O)CC7C6O7)O5)O)C)OC(=O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172383
PubChem CID:	49799449
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO10618	Acnistus arborescens	Species	Solanaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15104512]
NPO10618	Acnistus arborescens	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590148]
NPO10618	Acnistus arborescens	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10618	Acnistus arborescens	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	5

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	30000.0	nM	PMID[450924]
NPT1020	Organism	Pneumocystis carinii	Pneumocystis carinii	IC50	>	100000.0	nM	PMID[450924]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	28300.0	nM	PMID[450924]
NPT27	Others	Unspecified		IC50	=	15300.0	nM	PMID[450924]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[450924]

☑ 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 NPC469790 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	330
0.1-0.2	1942
0.2-0.3	5350
0.3-0.4	8433
0.4-0.5	12133
0.5-0.6	6794
0.6-0.7	5586
0.7-0.8	1909
0.8-0.85	165
0.85-0.9	40
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9649	High Similarity	NPC251226
0.9565	High Similarity	NPC159456
0.9565	High Similarity	NPC4021
0.9478	High Similarity	NPC154491
0.9478	High Similarity	NPC268530
0.9244	High Similarity	NPC203702
0.9244	High Similarity	NPC120994
0.9224	High Similarity	NPC42673
0.9217	High Similarity	NPC55296
0.906	High Similarity	NPC230513
0.9043	High Similarity	NPC284915
0.9035	High Similarity	NPC476163
0.8992	High Similarity	NPC269642
0.8926	High Similarity	NPC473635
0.8926	High Similarity	NPC293112
0.8917	High Similarity	NPC11895
0.8889	High Similarity	NPC58662
0.8862	High Similarity	NPC231529
0.8843	High Similarity	NPC81736
0.8843	High Similarity	NPC8374
0.8843	High Similarity	NPC172154
0.8833	High Similarity	NPC170538
0.8814	High Similarity	NPC113448
0.876	High Similarity	NPC469789
0.8739	High Similarity	NPC475041
0.8678	High Similarity	NPC88326
0.8678	High Similarity	NPC470265
0.8678	High Similarity	NPC23786
0.8678	High Similarity	NPC153700
0.8595	High Similarity	NPC67569
0.8537	High Similarity	NPC8369
0.8512	High Similarity	NPC474370
0.8462	Intermediate Similarity	NPC469655
0.8462	Intermediate Similarity	NPC469656
0.8462	Intermediate Similarity	NPC474846
0.8443	Intermediate Similarity	NPC46570
0.843	Intermediate Similarity	NPC264954
0.84	Intermediate Similarity	NPC287423
0.84	Intermediate Similarity	NPC471357
0.84	Intermediate Similarity	NPC469757
0.84	Intermediate Similarity	NPC117702
0.84	Intermediate Similarity	NPC146456
0.839	Intermediate Similarity	NPC42658
0.8374	Intermediate Similarity	NPC107493
0.8348	Intermediate Similarity	NPC470587
0.8347	Intermediate Similarity	NPC709
0.8347	Intermediate Similarity	NPC50774
0.8347	Intermediate Similarity	NPC240509
0.8346	Intermediate Similarity	NPC173347
0.8333	Intermediate Similarity	NPC311534
0.8319	Intermediate Similarity	NPC317210
0.8319	Intermediate Similarity	NPC962
0.8319	Intermediate Similarity	NPC250109
0.8306	Intermediate Similarity	NPC473979
0.8306	Intermediate Similarity	NPC471392
0.8306	Intermediate Similarity	NPC204812
0.8305	Intermediate Similarity	NPC94650
0.8293	Intermediate Similarity	NPC310511
0.8293	Intermediate Similarity	NPC470779
0.8291	Intermediate Similarity	NPC299590
0.8279	Intermediate Similarity	NPC475520
0.8279	Intermediate Similarity	NPC61520
0.8279	Intermediate Similarity	NPC472667
0.8279	Intermediate Similarity	NPC473203
0.8279	Intermediate Similarity	NPC5292
0.8276	Intermediate Similarity	NPC473165
0.8268	Intermediate Similarity	NPC86159
0.8268	Intermediate Similarity	NPC6108
0.8268	Intermediate Similarity	NPC219085
0.8268	Intermediate Similarity	NPC197707
0.8268	Intermediate Similarity	NPC180079
0.8268	Intermediate Similarity	NPC469755
0.8268	Intermediate Similarity	NPC17896
0.8268	Intermediate Similarity	NPC469753
0.8268	Intermediate Similarity	NPC9499
0.8268	Intermediate Similarity	NPC469754
0.8268	Intermediate Similarity	NPC469752
0.8268	Intermediate Similarity	NPC89514
0.8268	Intermediate Similarity	NPC469751
0.8268	Intermediate Similarity	NPC471352
0.8268	Intermediate Similarity	NPC471358
0.8268	Intermediate Similarity	NPC284406
0.8268	Intermediate Similarity	NPC10823
0.8268	Intermediate Similarity	NPC470880
0.8268	Intermediate Similarity	NPC471360
0.8268	Intermediate Similarity	NPC471361
0.8268	Intermediate Similarity	NPC221414
0.8268	Intermediate Similarity	NPC251866
0.8268	Intermediate Similarity	NPC70542
0.8268	Intermediate Similarity	NPC471359
0.8264	Intermediate Similarity	NPC470492
0.8264	Intermediate Similarity	NPC53396
0.8264	Intermediate Similarity	NPC478204
0.8264	Intermediate Similarity	NPC167606
0.8264	Intermediate Similarity	NPC98249
0.8264	Intermediate Similarity	NPC286528
0.8264	Intermediate Similarity	NPC20302
0.8264	Intermediate Similarity	NPC469684
0.8264	Intermediate Similarity	NPC13713
0.8264	Intermediate Similarity	NPC140055
0.8254	Intermediate Similarity	NPC470882
0.8254	Intermediate Similarity	NPC473253
0.824	Intermediate Similarity	NPC241456
0.824	Intermediate Similarity	NPC32868
0.8235	Intermediate Similarity	NPC476964
0.8226	Intermediate Similarity	NPC65858
0.8226	Intermediate Similarity	NPC222688
0.8211	Intermediate Similarity	NPC476961
0.8211	Intermediate Similarity	NPC79579
0.8211	Intermediate Similarity	NPC472004
0.8205	Intermediate Similarity	NPC469916
0.8205	Intermediate Similarity	NPC273155
0.8205	Intermediate Similarity	NPC472439
0.8203	Intermediate Similarity	NPC279478
0.8203	Intermediate Similarity	NPC241935
0.8197	Intermediate Similarity	NPC108581
0.8197	Intermediate Similarity	NPC329736
0.8197	Intermediate Similarity	NPC478206
0.8197	Intermediate Similarity	NPC284707
0.8197	Intermediate Similarity	NPC153440
0.8197	Intermediate Similarity	NPC478205
0.819	Intermediate Similarity	NPC295366
0.8189	Intermediate Similarity	NPC473620
0.8182	Intermediate Similarity	NPC49492
0.8182	Intermediate Similarity	NPC196931
0.8182	Intermediate Similarity	NPC469794
0.8182	Intermediate Similarity	NPC266728
0.8182	Intermediate Similarity	NPC190286
0.8182	Intermediate Similarity	NPC72772
0.8167	Intermediate Similarity	NPC33360
0.816	Intermediate Similarity	NPC265557
0.816	Intermediate Similarity	NPC135038
0.816	Intermediate Similarity	NPC18945
0.816	Intermediate Similarity	NPC67251
0.816	Intermediate Similarity	NPC55602
0.816	Intermediate Similarity	NPC91693
0.816	Intermediate Similarity	NPC105926
0.816	Intermediate Similarity	NPC27363
0.816	Intermediate Similarity	NPC43252
0.8154	Intermediate Similarity	NPC476823
0.814	Intermediate Similarity	NPC231240
0.814	Intermediate Similarity	NPC34963
0.814	Intermediate Similarity	NPC93416
0.814	Intermediate Similarity	NPC471855
0.813	Intermediate Similarity	NPC476960
0.813	Intermediate Similarity	NPC270850
0.813	Intermediate Similarity	NPC473636
0.813	Intermediate Similarity	NPC305260
0.813	Intermediate Similarity	NPC77689
0.813	Intermediate Similarity	NPC211093
0.813	Intermediate Similarity	NPC473839
0.8125	Intermediate Similarity	NPC35109
0.8125	Intermediate Similarity	NPC473593
0.8125	Intermediate Similarity	NPC476966
0.812	Intermediate Similarity	NPC180744
0.812	Intermediate Similarity	NPC471783
0.812	Intermediate Similarity	NPC9457
0.812	Intermediate Similarity	NPC166993
0.8115	Intermediate Similarity	NPC134430
0.8115	Intermediate Similarity	NPC183580
0.8115	Intermediate Similarity	NPC470493
0.8115	Intermediate Similarity	NPC312824
0.8115	Intermediate Similarity	NPC475809
0.811	Intermediate Similarity	NPC42399
0.811	Intermediate Similarity	NPC179412
0.811	Intermediate Similarity	NPC305496
0.811	Intermediate Similarity	NPC473265
0.811	Intermediate Similarity	NPC471356
0.811	Intermediate Similarity	NPC298841
0.8103	Intermediate Similarity	NPC65523
0.8099	Intermediate Similarity	NPC147912
0.8099	Intermediate Similarity	NPC67259
0.8095	Intermediate Similarity	NPC24651
0.8095	Intermediate Similarity	NPC473255
0.8095	Intermediate Similarity	NPC476729
0.8083	Intermediate Similarity	NPC269530
0.808	Intermediate Similarity	NPC312833
0.8077	Intermediate Similarity	NPC58029
0.8077	Intermediate Similarity	NPC104585
0.8077	Intermediate Similarity	NPC316915
0.8077	Intermediate Similarity	NPC157817
0.8077	Intermediate Similarity	NPC225385
0.8077	Intermediate Similarity	NPC469749
0.8077	Intermediate Similarity	NPC247190
0.8077	Intermediate Similarity	NPC298783
0.8077	Intermediate Similarity	NPC88668
0.8077	Intermediate Similarity	NPC116075
0.8077	Intermediate Similarity	NPC32793
0.8077	Intermediate Similarity	NPC146857
0.8077	Intermediate Similarity	NPC469673
0.8067	Intermediate Similarity	NPC76084
0.8065	Intermediate Similarity	NPC474585
0.8065	Intermediate Similarity	NPC143755
0.8062	Intermediate Similarity	NPC253456
0.8062	Intermediate Similarity	NPC16569
0.8062	Intermediate Similarity	NPC196921
0.8062	Intermediate Similarity	NPC220757
0.8062	Intermediate Similarity	NPC159338
0.8051	Intermediate Similarity	NPC112895
0.8051	Intermediate Similarity	NPC218123

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 NPC469790 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	2200
0.2-0.3	3821
0.3-0.4	1812
0.4-0.5	552
0.5-0.6	250
0.6-0.7	158
0.7-0.8	40
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8291	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8268	Intermediate Similarity	NPD7319	Approved
0.8264	Intermediate Similarity	NPD7115	Discovery
0.822	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD7507	Approved
0.7966	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6319	Approved
0.7698	Intermediate Similarity	NPD7516	Approved
0.7619	Intermediate Similarity	NPD7328	Approved
0.7619	Intermediate Similarity	NPD7327	Approved
0.7603	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD6008	Approved
0.7541	Intermediate Similarity	NPD6373	Approved
0.7541	Intermediate Similarity	NPD6372	Approved
0.7521	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.7458	Intermediate Similarity	NPD7639	Approved
0.7458	Intermediate Similarity	NPD7640	Approved
0.7442	Intermediate Similarity	NPD8033	Approved
0.7442	Intermediate Similarity	NPD8379	Approved
0.7442	Intermediate Similarity	NPD8296	Approved
0.7442	Intermediate Similarity	NPD8335	Approved
0.7442	Intermediate Similarity	NPD8380	Approved
0.7442	Intermediate Similarity	NPD8378	Approved
0.744	Intermediate Similarity	NPD4632	Approved
0.7438	Intermediate Similarity	NPD6402	Approved
0.7438	Intermediate Similarity	NPD5739	Approved
0.7438	Intermediate Similarity	NPD6675	Approved
0.7438	Intermediate Similarity	NPD7128	Approved
0.7419	Intermediate Similarity	NPD6650	Approved
0.7419	Intermediate Similarity	NPD6649	Approved
0.7405	Intermediate Similarity	NPD7492	Approved
0.7364	Intermediate Similarity	NPD8294	Approved
0.7364	Intermediate Similarity	NPD8377	Approved
0.7364	Intermediate Similarity	NPD6059	Approved
0.7364	Intermediate Similarity	NPD6054	Approved
0.7348	Intermediate Similarity	NPD6616	Approved
0.7333	Intermediate Similarity	NPD7632	Discontinued
0.7317	Intermediate Similarity	NPD7320	Approved
0.7317	Intermediate Similarity	NPD6899	Approved
0.7317	Intermediate Similarity	NPD6881	Approved
0.7293	Intermediate Similarity	NPD8293	Discontinued
0.7293	Intermediate Similarity	NPD7078	Approved
0.7266	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6370	Approved
0.7236	Intermediate Similarity	NPD5697	Approved
0.7236	Intermediate Similarity	NPD5701	Approved
0.7222	Intermediate Similarity	NPD6053	Discontinued
0.7222	Intermediate Similarity	NPD6882	Approved
0.72	Intermediate Similarity	NPD7290	Approved
0.72	Intermediate Similarity	NPD6371	Approved
0.72	Intermediate Similarity	NPD7102	Approved
0.72	Intermediate Similarity	NPD4634	Approved
0.72	Intermediate Similarity	NPD6883	Approved
0.7197	Intermediate Similarity	NPD7604	Phase 2
0.7197	Intermediate Similarity	NPD8328	Phase 3
0.7176	Intermediate Similarity	NPD6016	Approved
0.7176	Intermediate Similarity	NPD6015	Approved
0.7176	Intermediate Similarity	NPD7503	Approved
0.7165	Intermediate Similarity	NPD8133	Approved
0.7143	Intermediate Similarity	NPD6617	Approved
0.7143	Intermediate Similarity	NPD8130	Phase 1
0.7143	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD6869	Approved
0.7132	Intermediate Similarity	NPD6009	Approved
0.7121	Intermediate Similarity	NPD5988	Approved
0.712	Intermediate Similarity	NPD6013	Approved
0.712	Intermediate Similarity	NPD6014	Approved
0.712	Intermediate Similarity	NPD6012	Approved
0.712	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5344	Discontinued
0.7097	Intermediate Similarity	NPD6412	Phase 2
0.7083	Intermediate Similarity	NPD4225	Approved
0.7045	Intermediate Similarity	NPD6921	Approved
0.7045	Intermediate Similarity	NPD5983	Phase 2
0.704	Intermediate Similarity	NPD6686	Approved
0.704	Intermediate Similarity	NPD6011	Approved
0.7008	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4755	Approved
0.6963	Remote Similarity	NPD6336	Discontinued
0.6917	Remote Similarity	NPD8513	Phase 3
0.6911	Remote Similarity	NPD5211	Phase 2
0.6885	Remote Similarity	NPD4700	Approved
0.6885	Remote Similarity	NPD5285	Approved
0.6885	Remote Similarity	NPD4696	Approved
0.6885	Remote Similarity	NPD5286	Approved
0.6861	Remote Similarity	NPD6033	Approved
0.686	Remote Similarity	NPD6083	Phase 2
0.686	Remote Similarity	NPD6084	Phase 2
0.6829	Remote Similarity	NPD1700	Approved
0.6825	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6399	Phase 3
0.68	Remote Similarity	NPD5141	Approved
0.6794	Remote Similarity	NPD6274	Approved
0.6791	Remote Similarity	NPD8517	Approved
0.6791	Remote Similarity	NPD8516	Approved
0.6791	Remote Similarity	NPD8515	Approved
0.678	Remote Similarity	NPD46	Approved
0.678	Remote Similarity	NPD6698	Approved
0.6774	Remote Similarity	NPD5225	Approved
0.6774	Remote Similarity	NPD4633	Approved
0.6774	Remote Similarity	NPD5224	Approved
0.6774	Remote Similarity	NPD5226	Approved
0.6767	Remote Similarity	NPD7101	Approved
0.6767	Remote Similarity	NPD7100	Approved
0.6748	Remote Similarity	NPD6648	Approved
0.6746	Remote Similarity	NPD4768	Approved
0.6746	Remote Similarity	NPD4767	Approved
0.6723	Remote Similarity	NPD8034	Phase 2
0.6723	Remote Similarity	NPD8035	Phase 2
0.6721	Remote Similarity	NPD7902	Approved
0.672	Remote Similarity	NPD5175	Approved
0.672	Remote Similarity	NPD5174	Approved
0.6695	Remote Similarity	NPD5328	Approved
0.6694	Remote Similarity	NPD5223	Approved
0.6694	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD4159	Approved
0.6692	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.6641	Remote Similarity	NPD4730	Approved
0.6641	Remote Similarity	NPD4729	Approved
0.6617	Remote Similarity	NPD6317	Approved
0.6612	Remote Similarity	NPD7748	Approved
0.661	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD4754	Approved
0.6583	Remote Similarity	NPD7515	Phase 2
0.6583	Remote Similarity	NPD6079	Approved
0.6567	Remote Similarity	NPD6314	Approved
0.6567	Remote Similarity	NPD6313	Approved
0.6557	Remote Similarity	NPD5695	Phase 3
0.6544	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5251	Approved
0.6538	Remote Similarity	NPD5250	Approved
0.6538	Remote Similarity	NPD5247	Approved
0.6538	Remote Similarity	NPD5248	Approved
0.6538	Remote Similarity	NPD5249	Phase 3
0.6512	Remote Similarity	NPD5128	Approved
0.6504	Remote Similarity	NPD4697	Phase 3
0.65	Remote Similarity	NPD5785	Approved
0.6496	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD7260	Phase 2
0.6475	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6001	Approved
0.6475	Remote Similarity	NPD7900	Approved
0.6446	Remote Similarity	NPD7637	Suspended
0.6446	Remote Similarity	NPD5693	Phase 1
0.6441	Remote Similarity	NPD7334	Approved
0.6441	Remote Similarity	NPD5330	Approved
0.6441	Remote Similarity	NPD6409	Approved
0.6441	Remote Similarity	NPD3618	Phase 1
0.6441	Remote Similarity	NPD7521	Approved
0.6441	Remote Similarity	NPD7146	Approved
0.6441	Remote Similarity	NPD6684	Approved
0.6441	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6845	Suspended
0.6429	Remote Similarity	NPD8074	Phase 3
0.6417	Remote Similarity	NPD4753	Phase 2
0.6371	Remote Similarity	NPD5221	Approved
0.6371	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5222	Approved
0.6364	Remote Similarity	NPD5217	Approved
0.6364	Remote Similarity	NPD5215	Approved
0.6364	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5216	Approved
0.634	Remote Similarity	NPD7236	Approved
0.6333	Remote Similarity	NPD6903	Approved
0.6331	Remote Similarity	NPD6067	Discontinued
0.6325	Remote Similarity	NPD7799	Discontinued
0.632	Remote Similarity	NPD5173	Approved
0.6316	Remote Similarity	NPD6115	Approved
0.6316	Remote Similarity	NPD6118	Approved
0.6316	Remote Similarity	NPD6114	Approved
0.6316	Remote Similarity	NPD6697	Approved
0.6311	Remote Similarity	NPD7983	Approved
0.6311	Remote Similarity	NPD5281	Approved
0.6311	Remote Similarity	NPD5284	Approved
0.6296	Remote Similarity	NPD6868	Approved
0.629	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4629	Approved
0.629	Remote Similarity	NPD5210	Approved
0.6288	Remote Similarity	NPD5135	Approved
0.6288	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD5169	Approved
0.6281	Remote Similarity	NPD6080	Approved
0.6281	Remote Similarity	NPD6673	Approved
0.6281	Remote Similarity	NPD6904	Approved
0.6271	Remote Similarity	NPD3133	Approved
0.6271	Remote Similarity	NPD3665	Phase 1
0.6271	Remote Similarity	NPD4786	Approved
0.6271	Remote Similarity	NPD3666	Approved
0.626	Remote Similarity	NPD5779	Approved
0.626	Remote Similarity	NPD5778	Approved
0.625	Remote Similarity	NPD7524	Approved
0.6242	Remote Similarity	NPD7239	Suspended
0.6241	Remote Similarity	NPD5127	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