NPASS Compound

Structure

NPC77689 OpenBabel07101719512D 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 -4.1459 -4.3085 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 2 0 0 0 0 0 0 0 0 0 -3.3167 -4.7872 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 -3.3167 -5.7447 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 -0.8292 -3.3511 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 -2.4875 -4.3085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 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 2 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 2 1 6 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 36 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 41 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:	2.364
LogD:	1.575
LogS:	-4.379
# 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:	5.872
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:	-5.504
MDCK Permeability:	1.6932186554186046e-05
Pgp-inhibitor:	0.054
Pgp-substrate:	0.938
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.475
30% Bioavailability (F30%):	0.776

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.592
Plasma Protein Binding (PPB):	74.02945709228516%
Volume Distribution (VD):	0.551
Pgp-substrate:	20.515348434448242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.833
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.684
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.875
CYP3A4-substrate:	0.672

ADMET: Excretion

Clearance (CL):	1.848
Half-life (T1/2):	0.391

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.723
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.107
Rat Oral Acute Toxicity:	0.851
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.023
Carcinogencity:	0.945
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC77689

Natural Product ID:	NPC77689
*Common Name:**	Galphimine E
IUPAC Name:	n.a.
Synonyms:	Galphimine E
Standard InCHIKey:	MAASNULAYUTHCM-STODXTIPSA-N
Standard InCHI:	InChI=1S/C32H46O9/c1-18-10-11-27(4)12-14-29(6)24-23(36)25(41-20(3)34)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/h8-10,19,21,23-25,33,36,38H,11-17H2,1-7H3/t19-,21+,23+,24+,25+,27-,28+,29-,30-,31+,32+/m1/s1
SMILES:	CC1=CC[C@]2(C)CC[C@]3(C)[C@H]4[C@@H]([C@@H]([C@]5(COC(=O)C=C[C@H]5[C@]4(C)CC[C@@]3(C(=O)OC)[C@@]2(C1)O)[C@@H](C)O)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502176
PubChem CID:	21578019
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[522500]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	4.0	ug ml-1	PMID[522500]
NPT5198	Cell Line	OVCAR	Homo sapiens	ED50	>	4.0	ug ml-1	PMID[522500]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	>	4.0	ug ml-1	PMID[522500]

☑ 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 NPC77689 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	261
0.1-0.2	1474
0.2-0.3	3882
0.3-0.4	6480
0.4-0.5	11577
0.5-0.6	9431
0.6-0.7	5841
0.7-0.8	3297
0.8-0.85	389
0.85-0.9	56
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473636
0.9818	High Similarity	NPC473839
0.9818	High Similarity	NPC211093
0.9817	High Similarity	NPC134430
0.9636	High Similarity	NPC475809
0.945	High Similarity	NPC277769
0.9273	High Similarity	NPC90952
0.9273	High Similarity	NPC4573
0.8824	High Similarity	NPC473635
0.8807	High Similarity	NPC475036
0.8783	High Similarity	NPC473968
0.8761	High Similarity	NPC269530
0.876	High Similarity	NPC231529
0.8739	High Similarity	NPC475263
0.8739	High Similarity	NPC470922
0.8696	High Similarity	NPC44170
0.8696	High Similarity	NPC268954
0.8667	High Similarity	NPC293112
0.8655	High Similarity	NPC11895
0.8655	High Similarity	NPC67251
0.8655	High Similarity	NPC469789
0.8649	High Similarity	NPC473586
0.8632	High Similarity	NPC475775
0.8632	High Similarity	NPC476529
0.8609	High Similarity	NPC110861
0.8596	High Similarity	NPC476801
0.8583	High Similarity	NPC172154
0.8583	High Similarity	NPC81736
0.8583	High Similarity	NPC24651
0.8571	High Similarity	NPC269642
0.8571	High Similarity	NPC275539
0.8571	High Similarity	NPC23786
0.8571	High Similarity	NPC170538
0.8571	High Similarity	NPC189075
0.8571	High Similarity	NPC470265
0.8559	High Similarity	NPC109607
0.8559	High Similarity	NPC107338
0.8559	High Similarity	NPC476961
0.8559	High Similarity	NPC88349
0.8547	High Similarity	NPC251310
0.8537	High Similarity	NPC477197
0.8522	High Similarity	NPC25909
0.8522	High Similarity	NPC7921
0.8522	High Similarity	NPC208998
0.85	High Similarity	NPC91693
0.85	High Similarity	NPC265557
0.85	High Similarity	NPC18945
0.85	High Similarity	NPC105926
0.8487	Intermediate Similarity	NPC470779
0.8487	Intermediate Similarity	NPC67569
0.8487	Intermediate Similarity	NPC46570
0.8482	Intermediate Similarity	NPC110496
0.8462	Intermediate Similarity	NPC473590
0.8462	Intermediate Similarity	NPC476959
0.8462	Intermediate Similarity	NPC469684
0.8455	Intermediate Similarity	NPC476966
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	NPC234042
0.8435	Intermediate Similarity	NPC152117
0.8435	Intermediate Similarity	NPC470063
0.843	Intermediate Similarity	NPC8369
0.843	Intermediate Similarity	NPC476729
0.8417	Intermediate Similarity	NPC312833
0.8417	Intermediate Similarity	NPC107493
0.8407	Intermediate Similarity	NPC293850
0.8403	Intermediate Similarity	NPC48692
0.8403	Intermediate Similarity	NPC251226
0.84	Intermediate Similarity	NPC225791
0.84	Intermediate Similarity	NPC478151
0.8393	Intermediate Similarity	NPC477877
0.839	Intermediate Similarity	NPC284707
0.839	Intermediate Similarity	NPC297179
0.8378	Intermediate Similarity	NPC95899
0.8376	Intermediate Similarity	NPC470075
0.8374	Intermediate Similarity	NPC472270
0.8374	Intermediate Similarity	NPC477191
0.8374	Intermediate Similarity	NPC245094
0.8374	Intermediate Similarity	NPC477075
0.8374	Intermediate Similarity	NPC329923
0.8374	Intermediate Similarity	NPC23020
0.8374	Intermediate Similarity	NPC477194
0.8374	Intermediate Similarity	NPC112492
0.8374	Intermediate Similarity	NPC477078
0.8374	Intermediate Similarity	NPC477192
0.8374	Intermediate Similarity	NPC472268
0.8374	Intermediate Similarity	NPC475281
0.8374	Intermediate Similarity	NPC477193
0.8374	Intermediate Similarity	NPC472269
0.8362	Intermediate Similarity	NPC471204
0.8348	Intermediate Similarity	NPC171888
0.8348	Intermediate Similarity	NPC146945
0.8347	Intermediate Similarity	NPC473979
0.8333	Intermediate Similarity	NPC159456
0.8333	Intermediate Similarity	NPC472216
0.8333	Intermediate Similarity	NPC284828
0.8333	Intermediate Similarity	NPC173905
0.8333	Intermediate Similarity	NPC5475
0.8333	Intermediate Similarity	NPC476204
0.8333	Intermediate Similarity	NPC310546
0.8333	Intermediate Similarity	NPC4021
0.8333	Intermediate Similarity	NPC170084
0.832	Intermediate Similarity	NPC71391
0.832	Intermediate Similarity	NPC277212
0.832	Intermediate Similarity	NPC476776
0.832	Intermediate Similarity	NPC471855
0.832	Intermediate Similarity	NPC478152
0.832	Intermediate Similarity	NPC478154
0.832	Intermediate Similarity	NPC477195
0.832	Intermediate Similarity	NPC192765
0.832	Intermediate Similarity	NPC30279
0.832	Intermediate Similarity	NPC478150
0.832	Intermediate Similarity	NPC178264
0.832	Intermediate Similarity	NPC46823
0.832	Intermediate Similarity	NPC312650
0.832	Intermediate Similarity	NPC473918
0.832	Intermediate Similarity	NPC478153
0.8319	Intermediate Similarity	NPC469380
0.8319	Intermediate Similarity	NPC5292
0.8319	Intermediate Similarity	NPC475041
0.8319	Intermediate Similarity	NPC469488
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	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	NPC176513
0.8305	Intermediate Similarity	NPC58662
0.8305	Intermediate Similarity	NPC287343
0.8305	Intermediate Similarity	NPC122033
0.8305	Intermediate Similarity	NPC470854
0.8305	Intermediate Similarity	NPC474654
0.8305	Intermediate Similarity	NPC470959
0.8305	Intermediate Similarity	NPC55296
0.8305	Intermediate Similarity	NPC474483
0.8305	Intermediate Similarity	NPC98249
0.8305	Intermediate Similarity	NPC476965
0.8305	Intermediate Similarity	NPC97908
0.8305	Intermediate Similarity	NPC470775
0.8305	Intermediate Similarity	NPC53396
0.8293	Intermediate Similarity	NPC42399
0.8293	Intermediate Similarity	NPC298841
0.8293	Intermediate Similarity	NPC470882
0.8293	Intermediate Similarity	NPC470516
0.8291	Intermediate Similarity	NPC67259
0.8291	Intermediate Similarity	NPC147912
0.8288	Intermediate Similarity	NPC474709
0.8288	Intermediate Similarity	NPC283343
0.8288	Intermediate Similarity	NPC273668
0.8288	Intermediate Similarity	NPC258547
0.8276	Intermediate Similarity	NPC194951
0.8276	Intermediate Similarity	NPC474516
0.8276	Intermediate Similarity	NPC12046
0.8268	Intermediate Similarity	NPC110700
0.8268	Intermediate Similarity	NPC279915
0.8261	Intermediate Similarity	NPC472214
0.8261	Intermediate Similarity	NPC474567
0.8261	Intermediate Similarity	NPC5103
0.8261	Intermediate Similarity	NPC472215
0.825	Intermediate Similarity	NPC476127
0.825	Intermediate Similarity	NPC154491
0.825	Intermediate Similarity	NPC79579
0.825	Intermediate Similarity	NPC476150
0.825	Intermediate Similarity	NPC112038
0.825	Intermediate Similarity	NPC268530
0.8246	Intermediate Similarity	NPC473483
0.8246	Intermediate Similarity	NPC151393
0.8246	Intermediate Similarity	NPC476802
0.8246	Intermediate Similarity	NPC88701
0.8246	Intermediate Similarity	NPC89171
0.824	Intermediate Similarity	NPC311178
0.824	Intermediate Similarity	NPC476774
0.824	Intermediate Similarity	NPC134914
0.824	Intermediate Similarity	NPC476780
0.824	Intermediate Similarity	NPC173435
0.824	Intermediate Similarity	NPC262796
0.824	Intermediate Similarity	NPC478064
0.824	Intermediate Similarity	NPC476074
0.824	Intermediate Similarity	NPC329993
0.824	Intermediate Similarity	NPC172374
0.824	Intermediate Similarity	NPC173347
0.824	Intermediate Similarity	NPC271610
0.824	Intermediate Similarity	NPC478155

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 NPC77689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	1635
0.2-0.3	3499
0.3-0.4	2290
0.4-0.5	923
0.5-0.6	334
0.6-0.7	153
0.7-0.8	77
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
0.8151	Intermediate Similarity	NPD7115	Discovery
0.8016	Intermediate Similarity	NPD7319	Approved
0.7951	Intermediate Similarity	NPD6319	Approved
0.7931	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD7507	Approved
0.7903	Intermediate Similarity	NPD8328	Phase 3
0.7863	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD8297	Approved
0.7795	Intermediate Similarity	NPD7736	Approved
0.7778	Intermediate Similarity	NPD6686	Approved
0.7705	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD7638	Approved
0.7699	Intermediate Similarity	NPD4225	Approved
0.7647	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7640	Approved
0.7632	Intermediate Similarity	NPD7639	Approved
0.7603	Intermediate Similarity	NPD4632	Approved
0.76	Intermediate Similarity	NPD8513	Phase 3
0.76	Intermediate Similarity	NPD8516	Approved
0.76	Intermediate Similarity	NPD8515	Approved
0.76	Intermediate Similarity	NPD8517	Approved
0.7559	Intermediate Similarity	NPD7492	Approved
0.752	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD6616	Approved
0.7479	Intermediate Similarity	NPD6881	Approved
0.7479	Intermediate Similarity	NPD6899	Approved
0.746	Intermediate Similarity	NPD8033	Approved
0.7456	Intermediate Similarity	NPD7902	Approved
0.7442	Intermediate Similarity	NPD7078	Approved
0.744	Intermediate Similarity	NPD7516	Approved
0.7438	Intermediate Similarity	NPD6649	Approved
0.7438	Intermediate Similarity	NPD8130	Phase 1
0.7438	Intermediate Similarity	NPD6650	Approved
0.7417	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5344	Discontinued
0.7402	Intermediate Similarity	NPD6370	Approved
0.7395	Intermediate Similarity	NPD5697	Approved
0.7395	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD8294	Approved
0.7381	Intermediate Similarity	NPD8377	Approved
0.7377	Intermediate Similarity	NPD6882	Approved
0.736	Intermediate Similarity	NPD7328	Approved
0.736	Intermediate Similarity	NPD7327	Approved
0.7355	Intermediate Similarity	NPD4634	Approved
0.7355	Intermediate Similarity	NPD6883	Approved
0.7355	Intermediate Similarity	NPD7102	Approved
0.7355	Intermediate Similarity	NPD7290	Approved
0.7323	Intermediate Similarity	NPD7503	Approved
0.7323	Intermediate Similarity	NPD8379	Approved
0.7323	Intermediate Similarity	NPD6016	Approved
0.7323	Intermediate Similarity	NPD8296	Approved
0.7323	Intermediate Similarity	NPD6015	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
0.7311	Intermediate Similarity	NPD6402	Approved
0.7311	Intermediate Similarity	NPD7128	Approved
0.7311	Intermediate Similarity	NPD5739	Approved
0.7311	Intermediate Similarity	NPD6675	Approved
0.7308	Intermediate Similarity	NPD8293	Discontinued
0.7295	Intermediate Similarity	NPD6847	Approved
0.7295	Intermediate Similarity	NPD6869	Approved
0.7295	Intermediate Similarity	NPD6617	Approved
0.728	Intermediate Similarity	NPD6009	Approved
0.7273	Intermediate Similarity	NPD6012	Approved
0.7273	Intermediate Similarity	NPD6014	Approved
0.7273	Intermediate Similarity	NPD6373	Approved
0.7273	Intermediate Similarity	NPD6013	Approved
0.7273	Intermediate Similarity	NPD6372	Approved
0.7266	Intermediate Similarity	NPD5988	Approved
0.7257	Intermediate Similarity	NPD5779	Approved
0.7257	Intermediate Similarity	NPD5778	Approved
0.725	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6059	Approved
0.7236	Intermediate Similarity	NPD6053	Discontinued
0.7232	Intermediate Similarity	NPD6698	Approved
0.7232	Intermediate Similarity	NPD46	Approved
0.7213	Intermediate Similarity	NPD6371	Approved
0.7209	Intermediate Similarity	NPD7604	Phase 2
0.7193	Intermediate Similarity	NPD7900	Approved
0.7193	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7320	Approved
0.719	Intermediate Similarity	NPD6011	Approved
0.7188	Intermediate Similarity	NPD5983	Phase 2
0.7176	Intermediate Similarity	NPD8074	Phase 3
0.7168	Intermediate Similarity	NPD6411	Approved
0.7117	Intermediate Similarity	NPD3573	Approved
0.7107	Intermediate Similarity	NPD5701	Approved
0.7107	Intermediate Similarity	NPD6412	Phase 2
0.7099	Intermediate Similarity	NPD6336	Discontinued
0.708	Intermediate Similarity	NPD7838	Discovery
0.7059	Intermediate Similarity	NPD5211	Phase 2
0.7059	Intermediate Similarity	NPD7632	Discontinued
0.7034	Intermediate Similarity	NPD5286	Approved
0.7034	Intermediate Similarity	NPD4696	Approved
0.7034	Intermediate Similarity	NPD5285	Approved
0.7034	Intermediate Similarity	NPD6648	Approved
0.7025	Intermediate Similarity	NPD6008	Approved
0.7018	Intermediate Similarity	NPD6079	Approved
0.6991	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6101	Approved
0.6983	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5141	Approved
0.6917	Remote Similarity	NPD5224	Approved
0.6917	Remote Similarity	NPD5225	Approved
0.6917	Remote Similarity	NPD5226	Approved
0.6917	Remote Similarity	NPD4633	Approved
0.6899	Remote Similarity	NPD7100	Approved
0.6899	Remote Similarity	NPD7101	Approved
0.688	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.688	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD4755	Approved
0.686	Remote Similarity	NPD5174	Approved
0.686	Remote Similarity	NPD5175	Approved
0.6842	Remote Similarity	NPD5328	Approved
0.6838	Remote Similarity	NPD7260	Phase 2
0.6833	Remote Similarity	NPD5223	Approved
0.6822	Remote Similarity	NPD6335	Approved
0.681	Remote Similarity	NPD6399	Phase 3
0.6807	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6274	Approved
0.678	Remote Similarity	NPD5221	Approved
0.678	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5222	Approved
0.6774	Remote Similarity	NPD4730	Approved
0.6774	Remote Similarity	NPD4729	Approved
0.675	Remote Similarity	NPD4700	Approved
0.6744	Remote Similarity	NPD6317	Approved
0.6741	Remote Similarity	NPD6033	Approved
0.6724	Remote Similarity	NPD8034	Phase 2
0.6724	Remote Similarity	NPD8035	Phase 2
0.6723	Remote Similarity	NPD6084	Phase 2
0.6723	Remote Similarity	NPD6083	Phase 2
0.6723	Remote Similarity	NPD5173	Approved
0.6692	Remote Similarity	NPD6313	Approved
0.6692	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6637	Remote Similarity	NPD1694	Approved
0.6613	Remote Similarity	NPD4767	Approved
0.6613	Remote Similarity	NPD4768	Approved
0.6609	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7637	Suspended
0.6579	Remote Similarity	NPD3618	Phase 1
0.6567	Remote Similarity	NPD7829	Approved
0.6567	Remote Similarity	NPD7830	Approved
0.6541	Remote Similarity	NPD6908	Approved
0.6541	Remote Similarity	NPD6909	Approved
0.6541	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4202	Approved
0.6522	Remote Similarity	NPD7799	Discontinued
0.6508	Remote Similarity	NPD5128	Approved
0.65	Remote Similarity	NPD7839	Suspended
0.65	Remote Similarity	NPD4697	Phase 3
0.6496	Remote Similarity	NPD5785	Approved
0.6491	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5216	Approved
0.6484	Remote Similarity	NPD5217	Approved
0.6484	Remote Similarity	NPD5215	Approved
0.6479	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4754	Approved
0.6443	Remote Similarity	NPD7236	Approved
0.6435	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7334	Approved
0.6435	Remote Similarity	NPD6409	Approved
0.6435	Remote Similarity	NPD7521	Approved
0.6435	Remote Similarity	NPD7146	Approved
0.6435	Remote Similarity	NPD5330	Approved
0.6435	Remote Similarity	NPD6684	Approved
0.6429	Remote Similarity	NPD6845	Suspended
0.6417	Remote Similarity	NPD5695	Phase 3
0.641	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5169	Approved
0.6406	Remote Similarity	NPD5135	Approved
0.6406	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4786	Approved
0.6396	Remote Similarity	NPD7645	Phase 2
0.6393	Remote Similarity	NPD5696	Approved
0.6372	Remote Similarity	NPD3667	Approved
0.6364	Remote Similarity	NPD8368	Discontinued
0.6357	Remote Similarity	NPD5127	Approved
0.635	Remote Similarity	NPD8451	Approved
0.634	Remote Similarity	NPD7239	Suspended
0.6338	Remote Similarity	NPD8415	Approved
0.6333	Remote Similarity	NPD5282	Discontinued
0.6325	Remote Similarity	NPD6672	Approved
0.6325	Remote Similarity	NPD5737	Approved
0.6325	Remote Similarity	NPD6903	Approved
0.6324	Remote Similarity	NPD7642	Approved
0.6324	Remote Similarity	NPD6067	Discontinued

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