NPASS Compound

Structure

NPC473839 OpenBabel07101718312D 41 45 0 0 1 0 0 0 0 0999 V2000 -0.8292 -2.3936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4406 1.2186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6583 4.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6583 0.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1459 0.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8292 2.3936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6583 -2.8723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0653 1.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9987 1.5310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6583 -0.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6583 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4875 0.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6583 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0653 3.4693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 -1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8560 2.0813 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8292 4.3085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3167 1.9149 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4141 2.3936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6583 2.8723 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6583 1.9149 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4875 3.3511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8292 -1.4362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 0.4787 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4875 1.4362 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8292 1.4362 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3167 2.8723 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8292 0.4787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8108 2.1528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3716 2.3936 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4875 4.3085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8292 -0.4787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6583 -1.9149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9987 3.2562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8292 3.3511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 7 39 1 0 0 0 0 8 9 2 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 27 1 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 15 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 31 1 0 0 0 0 16 18 1 0 0 0 0 16 32 1 0 0 0 0 17 30 1 0 0 0 0 17 40 1 0 0 0 0 19 33 1 0 0 0 0 20 34 2 0 0 0 0 20 41 1 0 0 0 0 21 28 1 1 0 0 0 21 30 1 0 0 0 0 22 35 2 0 0 0 0 22 40 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 23 41 1 6 0 0 0 24 28 1 1 0 0 0 24 29 1 0 0 0 0 25 30 1 6 0 0 0 25 36 1 0 0 0 0 26 31 1 0 0 0 0 26 37 2 0 0 0 0 26 39 1 0 0 0 0 27 32 1 1 0 0 0 28 5 1 1 0 0 0 29 31 1 1 0 0 0 30 19 1 6 0 0 0 31 32 1 1 0 0 0 32 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	574.31
Volume:	585.175
LogP:	2.171
LogD:	1.857
LogS:	-3.94
# Rotatable Bonds:	5
TPSA:	139.59
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.263
Synthetic Accessibility Score:	5.92
Fsp3:	0.781
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:	-5.424
MDCK Permeability:	1.9435263311606832e-05
Pgp-inhibitor:	0.059
Pgp-substrate:	0.199
Human Intestinal Absorption (HIA):	0.554
20% Bioavailability (F20%):	0.924
30% Bioavailability (F30%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.881
Plasma Protein Binding (PPB):	62.85487365722656%
Volume Distribution (VD):	0.378
Pgp-substrate:	26.911376953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.595
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.865
CYP3A4-substrate:	0.721

ADMET: Excretion

Clearance (CL):	2.176
Half-life (T1/2):	0.149

ADMET: Toxicity

hERG Blockers:	0.567
Human Hepatotoxicity (H-HT):	0.692
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.851
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.018
Carcinogencity:	0.671
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC473839

Natural Product ID:	NPC473839
*Common Name:**	Galphimine I
IUPAC Name:	n.a.
Synonyms:	Galphimine I
Standard InCHIKey:	PLOHJRTXRRLBGH-UNWDUKARSA-N
Standard InCHI:	InChI=1S/C32H46O9/c1-18-10-11-27(4)12-14-29(6)24-23(41-20(3)34)25(36)30(19(2)33)17-40-22(35)9-8-21(30)28(24,5)13-15-31(29,26(37)39-7)32(27,38)16-18/h8-9,19,21,23-25,33,36,38H,1,10-17H2,2-7H3/t19?,21-,23-,24-,25-,27+,28-,29+,30+,31-,32-/m0/s1
SMILES:	COC(=O)[C@@]12CC[C@@]3([C@@H]([C@@]1(C)CC[C@@]1([C@@]2(O)CC(=C)CC1)C)[C@H](OC(=O)C)[C@@H]([C@@]1([C@H]3C=CC(=O)OC1)C(O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453168
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids

*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
NPO19117	Galphimia glauca	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398543]
NPO19117	Galphimia glauca	Species	Malpighiaceae	Eukaryota	sedative extracts	n.a.	n.a.	PMID[15104495]
NPO19117	Galphimia glauca	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441069]
NPO19117	Galphimia glauca	Species	Malpighiaceae	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
ED50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	4.0	ug ml-1	PMID[497452]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	4.0	ug ml-1	PMID[497452]
NPT5198	Cell Line	OVCAR	Homo sapiens	ED50	>	4.0	ug ml-1	PMID[497452]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	4.0	ug ml-1	PMID[497452]

☑ 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 NPC473839 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	265
0.1-0.2	1526
0.2-0.3	3980
0.3-0.4	6765
0.4-0.5	11888
0.5-0.6	9308
0.6-0.7	5555
0.7-0.8	2976
0.8-0.85	391
0.85-0.9	35
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC211093
0.9818	High Similarity	NPC473636
0.9818	High Similarity	NPC77689
0.9817	High Similarity	NPC475809
0.9636	High Similarity	NPC134430
0.945	High Similarity	NPC4573
0.9273	High Similarity	NPC277769
0.9099	High Similarity	NPC90952
0.8739	High Similarity	NPC475263
0.8696	High Similarity	NPC268954
0.8667	High Similarity	NPC473635
0.8649	High Similarity	NPC473586
0.8636	High Similarity	NPC475036
0.8621	High Similarity	NPC473968
0.8609	High Similarity	NPC110861
0.8607	High Similarity	NPC231529
0.8596	High Similarity	NPC269530
0.8583	High Similarity	NPC470922
0.8559	High Similarity	NPC88349
0.8537	High Similarity	NPC477197
0.8534	High Similarity	NPC44170
0.8512	High Similarity	NPC293112
0.85	High Similarity	NPC67251
0.85	High Similarity	NPC11895
0.85	High Similarity	NPC469789
0.8487	Intermediate Similarity	NPC470779
0.8475	Intermediate Similarity	NPC475775
0.8475	Intermediate Similarity	NPC476529
0.8455	Intermediate Similarity	NPC477079
0.8455	Intermediate Similarity	NPC470913
0.8455	Intermediate Similarity	NPC477196
0.8455	Intermediate Similarity	NPC477077
0.8455	Intermediate Similarity	NPC477076
0.8435	Intermediate Similarity	NPC470063
0.8435	Intermediate Similarity	NPC476801
0.843	Intermediate Similarity	NPC172154
0.843	Intermediate Similarity	NPC24651
0.843	Intermediate Similarity	NPC81736
0.8417	Intermediate Similarity	NPC470265
0.8417	Intermediate Similarity	NPC23786
0.8417	Intermediate Similarity	NPC170538
0.8417	Intermediate Similarity	NPC269642
0.8407	Intermediate Similarity	NPC189075
0.8407	Intermediate Similarity	NPC275539
0.8403	Intermediate Similarity	NPC107338
0.8403	Intermediate Similarity	NPC251226
0.8403	Intermediate Similarity	NPC109607
0.8403	Intermediate Similarity	NPC476961
0.84	Intermediate Similarity	NPC225791
0.84	Intermediate Similarity	NPC478151
0.8393	Intermediate Similarity	NPC477877
0.839	Intermediate Similarity	NPC251310
0.8376	Intermediate Similarity	NPC470075
0.8374	Intermediate Similarity	NPC477191
0.8374	Intermediate Similarity	NPC477075
0.8374	Intermediate Similarity	NPC475281
0.8374	Intermediate Similarity	NPC329923
0.8374	Intermediate Similarity	NPC23020
0.8374	Intermediate Similarity	NPC112492
0.8374	Intermediate Similarity	NPC477194
0.8374	Intermediate Similarity	NPC477078
0.8374	Intermediate Similarity	NPC477192
0.8374	Intermediate Similarity	NPC472268
0.8374	Intermediate Similarity	NPC472270
0.8374	Intermediate Similarity	NPC477193
0.8374	Intermediate Similarity	NPC472269
0.8362	Intermediate Similarity	NPC25909
0.8362	Intermediate Similarity	NPC7921
0.8362	Intermediate Similarity	NPC208998
0.8347	Intermediate Similarity	NPC105926
0.8347	Intermediate Similarity	NPC91693
0.8347	Intermediate Similarity	NPC18945
0.8347	Intermediate Similarity	NPC265557
0.8333	Intermediate Similarity	NPC159456
0.8333	Intermediate Similarity	NPC46570
0.8333	Intermediate Similarity	NPC67569
0.8333	Intermediate Similarity	NPC310546
0.8333	Intermediate Similarity	NPC4021
0.832	Intermediate Similarity	NPC312650
0.832	Intermediate Similarity	NPC277212
0.832	Intermediate Similarity	NPC476776
0.832	Intermediate Similarity	NPC478152
0.832	Intermediate Similarity	NPC478154
0.832	Intermediate Similarity	NPC477195
0.832	Intermediate Similarity	NPC71391
0.832	Intermediate Similarity	NPC192765
0.832	Intermediate Similarity	NPC478150
0.832	Intermediate Similarity	NPC478153
0.832	Intermediate Similarity	NPC30279
0.832	Intermediate Similarity	NPC178264
0.832	Intermediate Similarity	NPC46823
0.832	Intermediate Similarity	NPC473918
0.8319	Intermediate Similarity	NPC469380
0.8319	Intermediate Similarity	NPC110496
0.8306	Intermediate Similarity	NPC305793
0.8306	Intermediate Similarity	NPC1314
0.8306	Intermediate Similarity	NPC273878
0.8306	Intermediate Similarity	NPC141600
0.8306	Intermediate Similarity	NPC252657
0.8306	Intermediate Similarity	NPC476966
0.8306	Intermediate Similarity	NPC11577
0.8306	Intermediate Similarity	NPC244296
0.8306	Intermediate Similarity	NPC107536
0.8306	Intermediate Similarity	NPC9470
0.8306	Intermediate Similarity	NPC280029
0.8306	Intermediate Similarity	NPC115656
0.8306	Intermediate Similarity	NPC470518
0.8306	Intermediate Similarity	NPC472267
0.8306	Intermediate Similarity	NPC269484
0.8306	Intermediate Similarity	NPC252289
0.8306	Intermediate Similarity	NPC88311
0.8306	Intermediate Similarity	NPC470912
0.8306	Intermediate Similarity	NPC82380
0.8306	Intermediate Similarity	NPC97918
0.8305	Intermediate Similarity	NPC58662
0.8305	Intermediate Similarity	NPC473590
0.8305	Intermediate Similarity	NPC476959
0.8305	Intermediate Similarity	NPC55296
0.8305	Intermediate Similarity	NPC474483
0.8305	Intermediate Similarity	NPC469684
0.8293	Intermediate Similarity	NPC298841
0.8293	Intermediate Similarity	NPC470516
0.8288	Intermediate Similarity	NPC474709
0.8288	Intermediate Similarity	NPC283343
0.8288	Intermediate Similarity	NPC273668
0.8288	Intermediate Similarity	NPC258547
0.8279	Intermediate Similarity	NPC8369
0.8279	Intermediate Similarity	NPC476729
0.8276	Intermediate Similarity	NPC152117
0.8276	Intermediate Similarity	NPC234042
0.8268	Intermediate Similarity	NPC279915
0.8268	Intermediate Similarity	NPC110700
0.8264	Intermediate Similarity	NPC107493
0.8264	Intermediate Similarity	NPC312833
0.825	Intermediate Similarity	NPC476127
0.825	Intermediate Similarity	NPC154491
0.825	Intermediate Similarity	NPC476150
0.825	Intermediate Similarity	NPC268530
0.825	Intermediate Similarity	NPC48692
0.8246	Intermediate Similarity	NPC88701
0.8246	Intermediate Similarity	NPC293850
0.824	Intermediate Similarity	NPC311178
0.824	Intermediate Similarity	NPC476774
0.824	Intermediate Similarity	NPC134914
0.824	Intermediate Similarity	NPC173435
0.824	Intermediate Similarity	NPC262796
0.824	Intermediate Similarity	NPC478064
0.824	Intermediate Similarity	NPC264566
0.824	Intermediate Similarity	NPC329993
0.824	Intermediate Similarity	NPC271610
0.824	Intermediate Similarity	NPC478155
0.824	Intermediate Similarity	NPC301639
0.824	Intermediate Similarity	NPC476074
0.824	Intermediate Similarity	NPC475377
0.824	Intermediate Similarity	NPC478065
0.824	Intermediate Similarity	NPC43589
0.824	Intermediate Similarity	NPC45346
0.824	Intermediate Similarity	NPC172374
0.824	Intermediate Similarity	NPC475167
0.824	Intermediate Similarity	NPC25998
0.824	Intermediate Similarity	NPC300655
0.824	Intermediate Similarity	NPC222951
0.824	Intermediate Similarity	NPC476780
0.824	Intermediate Similarity	NPC476775
0.8235	Intermediate Similarity	NPC284707
0.8235	Intermediate Similarity	NPC124676
0.8235	Intermediate Similarity	NPC146280
0.8235	Intermediate Similarity	NPC297179
0.8226	Intermediate Similarity	NPC245094
0.822	Intermediate Similarity	NPC89929
0.822	Intermediate Similarity	NPC471816
0.8214	Intermediate Similarity	NPC225238
0.8214	Intermediate Similarity	NPC476889
0.8214	Intermediate Similarity	NPC95899
0.8211	Intermediate Similarity	NPC297950
0.8205	Intermediate Similarity	NPC477126
0.8205	Intermediate Similarity	NPC471204
0.8198	Intermediate Similarity	NPC473160
0.8198	Intermediate Similarity	NPC476132
0.8198	Intermediate Similarity	NPC471412
0.8197	Intermediate Similarity	NPC473979
0.8197	Intermediate Similarity	NPC473802
0.819	Intermediate Similarity	NPC171888
0.819	Intermediate Similarity	NPC474846
0.819	Intermediate Similarity	NPC469655
0.819	Intermediate Similarity	NPC470076
0.819	Intermediate Similarity	NPC146945
0.819	Intermediate Similarity	NPC469656
0.8189	Intermediate Similarity	NPC476778
0.8189	Intermediate Similarity	NPC476777
0.8182	Intermediate Similarity	NPC170084
0.8182	Intermediate Similarity	NPC476204
0.8175	Intermediate Similarity	NPC475177
0.8175	Intermediate Similarity	NPC473679
0.8175	Intermediate Similarity	NPC324933
0.8175	Intermediate Similarity	NPC475444
0.8175	Intermediate Similarity	NPC471855
0.8175	Intermediate Similarity	NPC319719
0.8175	Intermediate Similarity	NPC233223
0.8175	Intermediate Similarity	NPC183816

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 NPC473839 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	1699
0.2-0.3	3502
0.3-0.4	2288
0.4-0.5	883
0.5-0.6	331
0.6-0.7	160
0.7-0.8	40
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8016	Intermediate Similarity	NPD7319	Approved
0.8	Intermediate Similarity	NPD7115	Discovery
0.7931	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD7507	Approved
0.7903	Intermediate Similarity	NPD8328	Phase 3
0.7805	Intermediate Similarity	NPD6319	Approved
0.7778	Intermediate Similarity	NPD6686	Approved
0.7712	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD7638	Approved
0.7699	Intermediate Similarity	NPD4225	Approved
0.7667	Intermediate Similarity	NPD8297	Approved
0.7656	Intermediate Similarity	NPD7736	Approved
0.7632	Intermediate Similarity	NPD7640	Approved
0.7632	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7748	Approved
0.746	Intermediate Similarity	NPD8516	Approved
0.746	Intermediate Similarity	NPD8033	Approved
0.746	Intermediate Similarity	NPD8513	Phase 3
0.746	Intermediate Similarity	NPD8517	Approved
0.746	Intermediate Similarity	NPD8515	Approved
0.7459	Intermediate Similarity	NPD4632	Approved
0.7456	Intermediate Similarity	NPD7902	Approved
0.744	Intermediate Similarity	NPD7516	Approved
0.7422	Intermediate Similarity	NPD7492	Approved
0.7414	Intermediate Similarity	NPD5344	Discontinued
0.7381	Intermediate Similarity	NPD6054	Approved
0.7381	Intermediate Similarity	NPD8294	Approved
0.7381	Intermediate Similarity	NPD8377	Approved
0.7364	Intermediate Similarity	NPD6616	Approved
0.736	Intermediate Similarity	NPD7328	Approved
0.736	Intermediate Similarity	NPD7327	Approved
0.7333	Intermediate Similarity	NPD6881	Approved
0.7333	Intermediate Similarity	NPD6899	Approved
0.7323	Intermediate Similarity	NPD8379	Approved
0.7323	Intermediate Similarity	NPD8296	Approved
0.7323	Intermediate Similarity	NPD6921	Approved
0.7323	Intermediate Similarity	NPD8378	Approved
0.7323	Intermediate Similarity	NPD8380	Approved
0.7323	Intermediate Similarity	NPD8335	Approved
0.7321	Intermediate Similarity	NPD7983	Approved
0.7321	Intermediate Similarity	NPD7515	Phase 2
0.7317	Intermediate Similarity	NPD8133	Approved
0.7308	Intermediate Similarity	NPD7078	Approved
0.7295	Intermediate Similarity	NPD6649	Approved
0.7295	Intermediate Similarity	NPD8130	Phase 1
0.7295	Intermediate Similarity	NPD6650	Approved
0.7273	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6370	Approved
0.725	Intermediate Similarity	NPD5697	Approved
0.725	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6882	Approved
0.7232	Intermediate Similarity	NPD6698	Approved
0.7232	Intermediate Similarity	NPD46	Approved
0.7213	Intermediate Similarity	NPD7102	Approved
0.7213	Intermediate Similarity	NPD4634	Approved
0.7213	Intermediate Similarity	NPD6883	Approved
0.7213	Intermediate Similarity	NPD7290	Approved
0.7213	Intermediate Similarity	NPD6371	Approved
0.7193	Intermediate Similarity	NPD7900	Approved
0.7193	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6015	Approved
0.7188	Intermediate Similarity	NPD7503	Approved
0.7188	Intermediate Similarity	NPD6016	Approved
0.7176	Intermediate Similarity	NPD8293	Discontinued
0.7167	Intermediate Similarity	NPD5739	Approved
0.7167	Intermediate Similarity	NPD7128	Approved
0.7167	Intermediate Similarity	NPD6675	Approved
0.7167	Intermediate Similarity	NPD6402	Approved
0.7154	Intermediate Similarity	NPD6617	Approved
0.7154	Intermediate Similarity	NPD6869	Approved
0.7154	Intermediate Similarity	NPD6847	Approved
0.7143	Intermediate Similarity	NPD6009	Approved
0.7132	Intermediate Similarity	NPD5988	Approved
0.7131	Intermediate Similarity	NPD6014	Approved
0.7131	Intermediate Similarity	NPD6372	Approved
0.7131	Intermediate Similarity	NPD6012	Approved
0.7131	Intermediate Similarity	NPD6013	Approved
0.7131	Intermediate Similarity	NPD6373	Approved
0.7109	Intermediate Similarity	NPD6059	Approved
0.7105	Intermediate Similarity	NPD5779	Approved
0.7105	Intermediate Similarity	NPD5778	Approved
0.7097	Intermediate Similarity	NPD6053	Discontinued
0.708	Intermediate Similarity	NPD7838	Discovery
0.7077	Intermediate Similarity	NPD7604	Phase 2
0.7059	Intermediate Similarity	NPD7632	Discontinued
0.7054	Intermediate Similarity	NPD5983	Phase 2
0.7049	Intermediate Similarity	NPD7320	Approved
0.7049	Intermediate Similarity	NPD6011	Approved
0.7045	Intermediate Similarity	NPD8074	Phase 3
0.7034	Intermediate Similarity	NPD6648	Approved
0.7018	Intermediate Similarity	NPD6411	Approved
0.6983	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6336	Discontinued
0.6967	Remote Similarity	NPD6412	Phase 2
0.6967	Remote Similarity	NPD5701	Approved
0.6964	Remote Similarity	NPD3573	Approved
0.6917	Remote Similarity	NPD5211	Phase 2
0.6891	Remote Similarity	NPD5286	Approved
0.6891	Remote Similarity	NPD5285	Approved
0.6891	Remote Similarity	NPD4696	Approved
0.6885	Remote Similarity	NPD6008	Approved
0.688	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8034	Phase 2
0.687	Remote Similarity	NPD8035	Phase 2
0.687	Remote Similarity	NPD6079	Approved
0.6842	Remote Similarity	NPD6101	Approved
0.6842	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5141	Approved
0.6777	Remote Similarity	NPD4633	Approved
0.6777	Remote Similarity	NPD5226	Approved
0.6777	Remote Similarity	NPD5225	Approved
0.6777	Remote Similarity	NPD5224	Approved
0.6769	Remote Similarity	NPD7100	Approved
0.6769	Remote Similarity	NPD7101	Approved
0.6746	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4755	Approved
0.6721	Remote Similarity	NPD5174	Approved
0.6721	Remote Similarity	NPD5175	Approved
0.6715	Remote Similarity	NPD7260	Phase 2
0.6696	Remote Similarity	NPD5328	Approved
0.6694	Remote Similarity	NPD5223	Approved
0.6692	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD6274	Approved
0.664	Remote Similarity	NPD4730	Approved
0.664	Remote Similarity	NPD4729	Approved
0.6639	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5221	Approved
0.6639	Remote Similarity	NPD5222	Approved
0.6637	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6033	Approved
0.6615	Remote Similarity	NPD6317	Approved
0.6612	Remote Similarity	NPD4700	Approved
0.6583	Remote Similarity	NPD6083	Phase 2
0.6583	Remote Similarity	NPD5173	Approved
0.6583	Remote Similarity	NPD6084	Phase 2
0.6581	Remote Similarity	NPD7637	Suspended
0.6567	Remote Similarity	NPD7829	Approved
0.6567	Remote Similarity	NPD7830	Approved
0.6565	Remote Similarity	NPD6313	Approved
0.6565	Remote Similarity	NPD6314	Approved
0.6538	Remote Similarity	NPD6868	Approved
0.6535	Remote Similarity	NPD5248	Approved
0.6535	Remote Similarity	NPD5251	Approved
0.6535	Remote Similarity	NPD5247	Approved
0.6535	Remote Similarity	NPD5249	Phase 3
0.6535	Remote Similarity	NPD5250	Approved
0.65	Remote Similarity	NPD7839	Suspended
0.6496	Remote Similarity	NPD5785	Approved
0.6491	Remote Similarity	NPD1694	Approved
0.648	Remote Similarity	NPD4767	Approved
0.648	Remote Similarity	NPD4768	Approved
0.6479	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD3618	Phase 1
0.642	Remote Similarity	NPD7799	Discontinued
0.6418	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD6909	Approved
0.6418	Remote Similarity	NPD6908	Approved
0.6396	Remote Similarity	NPD7645	Phase 2
0.6387	Remote Similarity	NPD4202	Approved
0.6378	Remote Similarity	NPD5128	Approved
0.6364	Remote Similarity	NPD4697	Phase 3
0.6357	Remote Similarity	NPD5217	Approved
0.6357	Remote Similarity	NPD5215	Approved
0.6357	Remote Similarity	NPD5216	Approved
0.635	Remote Similarity	NPD8451	Approved
0.6338	Remote Similarity	NPD8415	Approved
0.6333	Remote Similarity	NPD5282	Discontinued
0.6333	Remote Similarity	NPD7236	Approved
0.6324	Remote Similarity	NPD7642	Approved
0.632	Remote Similarity	NPD4754	Approved
0.6312	Remote Similarity	NPD6845	Suspended
0.6304	Remote Similarity	NPD8448	Approved
0.6294	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7146	Approved
0.6293	Remote Similarity	NPD6409	Approved
0.6293	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7334	Approved
0.6293	Remote Similarity	NPD5330	Approved
0.6293	Remote Similarity	NPD7521	Approved
0.6293	Remote Similarity	NPD6684	Approved
0.6286	Remote Similarity	NPD8390	Approved
0.6286	Remote Similarity	NPD8392	Approved
0.6286	Remote Similarity	NPD8391	Approved
0.6281	Remote Similarity	NPD5695	Phase 3
0.6279	Remote Similarity	NPD5169	Approved
0.6279	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5135	Approved
0.6271	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD8368	Discontinued
0.6261	Remote Similarity	NPD4786	Approved
0.626	Remote Similarity	NPD5696	Approved
0.6239	Remote Similarity	NPD7524	Approved
0.6234	Remote Similarity	NPD7239	Suspended

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