NPASS Compound

Structure

NPC475036 OpenBabel07101718282D 40 43 0 0 1 0 0 0 0 0999 V2000 2.5390 -0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6976 -2.3123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 -2.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 -5.8636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 -2.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 -2.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5390 -3.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 -1.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 0.9773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7204 -2.3123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2090 -1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3854 -1.9545 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5390 -4.3977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5390 -0.4886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2317 -0.4886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8463 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9773 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5390 -1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6927 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2317 -1.4659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8463 -0.4886 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 -4.2317 -3.1586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6976 -0.6196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 -4.8864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3854 0.9773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0781 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 -0.9773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6927 -4.8864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -2.4432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 3 26 1 0 0 0 0 5 28 1 0 0 0 0 6 39 1 0 0 0 0 7 40 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 18 2 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 16 31 1 0 0 0 0 17 32 1 0 0 0 0 19 2 1 1 0 0 0 19 29 1 0 0 0 0 19 33 1 0 0 0 0 20 27 1 6 0 0 0 20 29 1 0 0 0 0 21 34 2 0 0 0 0 21 39 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 35 1 1 0 0 0 23 27 1 6 0 0 0 23 28 1 0 0 0 0 24 29 1 1 0 0 0 24 36 1 0 0 0 0 25 30 1 0 0 0 0 25 37 2 0 0 0 0 25 40 1 0 0 0 0 26 31 1 6 0 0 0 27 4 1 6 0 0 0 28 30 1 6 0 0 0 29 17 1 6 0 0 0 30 31 1 6 0 0 0 31 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	566.35
Volume:	581.709
LogP:	2.169
LogD:	1.625
LogS:	-3.826
# Rotatable Bonds:	8
TPSA:	153.75
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.241
Synthetic Accessibility Score:	5.805
Fsp3:	0.871
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:	-5.563
MDCK Permeability:	1.8719039871939458e-05
Pgp-inhibitor:	0.229
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.073
20% Bioavailability (F20%):	0.067
30% Bioavailability (F30%):	0.295

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.246
Plasma Protein Binding (PPB):	44.431983947753906%
Volume Distribution (VD):	0.565
Pgp-substrate:	22.582902908325195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.85
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.504

ADMET: Excretion

Clearance (CL):	2.499
Half-life (T1/2):	0.495

ADMET: Toxicity

hERG Blockers:	0.221
Human Hepatotoxicity (H-HT):	0.689
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.171
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.055
Carcinogencity:	0.888
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC475036

Natural Product ID:	NPC475036
*Common Name:**	Methyl (4As,4Bs,6As,7S,8R,9R,10S,10As,10Br,12As)-4A,9,10-Trihydroxy-8-[(1R)-1-Hydroxyethyl]-8-(Hydroxymethyl)-7-(3-Methoxy-3-Oxopropyl)-3,6A,10B,12A-Tetramethyl-1,4,5,6,7,9,10,10A,11,12-Decahydrochrysene-4B-Carboxylate
IUPAC Name:	methyl (4aS,4bS,6aS,7S,8R,9R,10S,10aS,10bR,12aS)-4a,9,10-trihydroxy-8-[(1R)-1-hydroxyethyl]-8-(hydroxymethyl)-7-(3-methoxy-3-oxopropyl)-3,6a,10b,12a-tetramethyl-1,4,5,6,7,9,10,10a,11,12-decahydrochrysene-4b-carboxylate
Synonyms:
Standard InCHIKey:	RBKYLTMXHKKOOD-ISGLCVLNSA-N
Standard InCHI:	InChI=1S/C31H50O9/c1-18-10-11-26(3)12-14-28(5)23-22(35)24(36)29(17-32,19(2)33)20(8-9-21(34)39-6)27(23,4)13-15-30(28,25(37)40-7)31(26,38)16-18/h10,19-20,22-24,32-33,35-36,38H,8-9,11-17H2,1-7H3/t19-,20+,22+,23+,24+,26-,27+,28-,29-,30+,31+/m1/s1
SMILES:	CC1=CCC2(CCC3(C4C(C(C(C(C4(CCC3(C2(C1)O)C(=O)OC)C)CCC(=O)OC)(CO)C(C)O)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL493644
PubChem CID:	44566235
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	76.8	%	PMID[527388]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	61.8	%	PMID[527388]

☑ 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 NPC475036 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	235
0.1-0.2	1430
0.2-0.3	4267
0.3-0.4	7909
0.4-0.5	13140
0.5-0.6	6769
0.6-0.7	5284
0.7-0.8	2979
0.8-0.85	574
0.85-0.9	104
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.899	High Similarity	NPC35239
0.8972	High Similarity	NPC134430
0.8922	High Similarity	NPC477877
0.89	High Similarity	NPC256247
0.8889	High Similarity	NPC111214
0.8889	High Similarity	NPC271614
0.8889	High Similarity	NPC29765
0.8878	High Similarity	NPC476327
0.8878	High Similarity	NPC25848
0.8878	High Similarity	NPC476318
0.8878	High Similarity	NPC19376
0.8878	High Similarity	NPC307282
0.8878	High Similarity	NPC305464
0.8878	High Similarity	NPC201657
0.8868	High Similarity	NPC7921
0.8868	High Similarity	NPC208998
0.8857	High Similarity	NPC171888
0.8857	High Similarity	NPC146945
0.8824	High Similarity	NPC284865
0.8807	High Similarity	NPC77689
0.8807	High Similarity	NPC473636
0.8796	High Similarity	NPC475809
0.8788	High Similarity	NPC106112
0.8788	High Similarity	NPC247139
0.8788	High Similarity	NPC255589
0.8788	High Similarity	NPC9613
0.8788	High Similarity	NPC261935
0.8788	High Similarity	NPC43686
0.8788	High Similarity	NPC259788
0.8776	High Similarity	NPC473240
0.8776	High Similarity	NPC32118
0.875	High Similarity	NPC293850
0.8725	High Similarity	NPC225238
0.8716	High Similarity	NPC297179
0.8713	High Similarity	NPC476132
0.87	High Similarity	NPC260149
0.87	High Similarity	NPC58942
0.8687	High Similarity	NPC132824
0.8687	High Similarity	NPC207922
0.8687	High Similarity	NPC259733
0.8687	High Similarity	NPC73004
0.8687	High Similarity	NPC204961
0.8687	High Similarity	NPC173744
0.8687	High Similarity	NPC158371
0.8673	High Similarity	NPC299996
0.8673	High Similarity	NPC88116
0.8673	High Similarity	NPC231063
0.8673	High Similarity	NPC145667
0.8673	High Similarity	NPC32407
0.8673	High Similarity	NPC263548
0.8673	High Similarity	NPC282395
0.8673	High Similarity	NPC20235
0.8636	High Similarity	NPC473839
0.8636	High Similarity	NPC211093
0.8624	High Similarity	NPC470854
0.8624	High Similarity	NPC287343
0.8624	High Similarity	NPC122033
0.8624	High Similarity	NPC470775
0.8624	High Similarity	NPC176513
0.8624	High Similarity	NPC474654
0.8624	High Similarity	NPC97908
0.8614	High Similarity	NPC476195
0.8611	High Similarity	NPC475633
0.86	High Similarity	NPC189880
0.8598	High Similarity	NPC277769
0.8598	High Similarity	NPC48249
0.8586	High Similarity	NPC96916
0.8571	High Similarity	NPC133579
0.8571	High Similarity	NPC136313
0.8571	High Similarity	NPC474806
0.8571	High Similarity	NPC307335
0.8571	High Similarity	NPC275809
0.8571	High Similarity	NPC74855
0.8558	High Similarity	NPC80566
0.8545	High Similarity	NPC17772
0.8545	High Similarity	NPC204552
0.8545	High Similarity	NPC251310
0.8545	High Similarity	NPC188667
0.8545	High Similarity	NPC470776
0.8544	High Similarity	NPC90177
0.8532	High Similarity	NPC40632
0.8532	High Similarity	NPC152199
0.8532	High Similarity	NPC474046
0.8532	High Similarity	NPC96312
0.8532	High Similarity	NPC134869
0.8532	High Similarity	NPC251236
0.8532	High Similarity	NPC235539
0.8532	High Similarity	NPC259306
0.8532	High Similarity	NPC474734
0.8532	High Similarity	NPC328374
0.8532	High Similarity	NPC470628
0.8529	High Similarity	NPC54909
0.8529	High Similarity	NPC233012
0.8519	High Similarity	NPC269315
0.8519	High Similarity	NPC475208
0.8519	High Similarity	NPC49451
0.8519	High Similarity	NPC238935
0.8519	High Similarity	NPC271138
0.8515	High Similarity	NPC174663
0.8515	High Similarity	NPC188833
0.8515	High Similarity	NPC475876
0.8505	High Similarity	NPC31839
0.85	High Similarity	NPC88847
0.8491	Intermediate Similarity	NPC218853
0.8491	Intermediate Similarity	NPC310546
0.8491	Intermediate Similarity	NPC143706
0.8491	Intermediate Similarity	NPC472534
0.8485	Intermediate Similarity	NPC159365
0.8485	Intermediate Similarity	NPC6818
0.8485	Intermediate Similarity	NPC470958
0.8485	Intermediate Similarity	NPC191412
0.8485	Intermediate Similarity	NPC474529
0.8485	Intermediate Similarity	NPC470957
0.8485	Intermediate Similarity	NPC114159
0.8482	Intermediate Similarity	NPC75417
0.8476	Intermediate Similarity	NPC59530
0.8469	Intermediate Similarity	NPC966
0.8469	Intermediate Similarity	NPC288833
0.8469	Intermediate Similarity	NPC84319
0.8469	Intermediate Similarity	NPC282616
0.8469	Intermediate Similarity	NPC71074
0.8469	Intermediate Similarity	NPC25299
0.8469	Intermediate Similarity	NPC52021
0.8469	Intermediate Similarity	NPC300351
0.8469	Intermediate Similarity	NPC306541
0.8469	Intermediate Similarity	NPC472149
0.8469	Intermediate Similarity	NPC235884
0.8469	Intermediate Similarity	NPC228784
0.8469	Intermediate Similarity	NPC324341
0.8469	Intermediate Similarity	NPC155120
0.8462	Intermediate Similarity	NPC65523
0.8455	Intermediate Similarity	NPC473590
0.844	Intermediate Similarity	NPC469877
0.844	Intermediate Similarity	NPC470919
0.844	Intermediate Similarity	NPC473798
0.844	Intermediate Similarity	NPC117712
0.844	Intermediate Similarity	NPC474906
0.844	Intermediate Similarity	NPC243354
0.844	Intermediate Similarity	NPC18547
0.8426	Intermediate Similarity	NPC80843
0.8426	Intermediate Similarity	NPC46388
0.8426	Intermediate Similarity	NPC90952
0.8426	Intermediate Similarity	NPC280782
0.8426	Intermediate Similarity	NPC116794
0.8426	Intermediate Similarity	NPC474516
0.8426	Intermediate Similarity	NPC289312
0.8426	Intermediate Similarity	NPC11252
0.8426	Intermediate Similarity	NPC4573
0.8426	Intermediate Similarity	NPC302146
0.8426	Intermediate Similarity	NPC37739
0.8426	Intermediate Similarity	NPC1046
0.8416	Intermediate Similarity	NPC476879
0.8416	Intermediate Similarity	NPC187933
0.8416	Intermediate Similarity	NPC476878
0.8411	Intermediate Similarity	NPC220984
0.8411	Intermediate Similarity	NPC7870
0.8411	Intermediate Similarity	NPC242611
0.8411	Intermediate Similarity	NPC274507
0.8411	Intermediate Similarity	NPC102914
0.8411	Intermediate Similarity	NPC75747
0.8411	Intermediate Similarity	NPC199457
0.8411	Intermediate Similarity	NPC68419
0.8411	Intermediate Similarity	NPC108709
0.8411	Intermediate Similarity	NPC110139
0.84	Intermediate Similarity	NPC23241
0.84	Intermediate Similarity	NPC266899
0.84	Intermediate Similarity	NPC195715
0.84	Intermediate Similarity	NPC53565
0.84	Intermediate Similarity	NPC474727
0.8396	Intermediate Similarity	NPC273155
0.8393	Intermediate Similarity	NPC112038
0.8384	Intermediate Similarity	NPC158059
0.8384	Intermediate Similarity	NPC229281
0.8384	Intermediate Similarity	NPC202728
0.8384	Intermediate Similarity	NPC118519
0.8381	Intermediate Similarity	NPC472655
0.8381	Intermediate Similarity	NPC278628
0.8381	Intermediate Similarity	NPC102352
0.8381	Intermediate Similarity	NPC470587
0.8381	Intermediate Similarity	NPC231530
0.8378	Intermediate Similarity	NPC286347
0.8367	Intermediate Similarity	NPC86372
0.8367	Intermediate Similarity	NPC49320
0.8367	Intermediate Similarity	NPC172361
0.8367	Intermediate Similarity	NPC126369
0.8367	Intermediate Similarity	NPC130278
0.8367	Intermediate Similarity	NPC470589
0.8367	Intermediate Similarity	NPC111110
0.8365	Intermediate Similarity	NPC95899
0.8364	Intermediate Similarity	NPC207217
0.835	Intermediate Similarity	NPC118964
0.8349	Intermediate Similarity	NPC477266
0.8349	Intermediate Similarity	NPC47063
0.8349	Intermediate Similarity	NPC138334
0.8349	Intermediate Similarity	NPC194273
0.8349	Intermediate Similarity	NPC204458
0.8349	Intermediate Similarity	NPC189884
0.8333	Intermediate Similarity	NPC30397
0.8333	Intermediate Similarity	NPC477875
0.8333	Intermediate Similarity	NPC108748

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 NPC475036 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1766
0.2-0.3	3690
0.3-0.4	2174
0.4-0.5	796
0.5-0.6	260
0.6-0.7	185
0.7-0.8	70
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
0.8125	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD8328	Phase 3
0.7921	Intermediate Similarity	NPD7515	Phase 2
0.7913	Intermediate Similarity	NPD6319	Approved
0.789	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD7748	Approved
0.7745	Intermediate Similarity	NPD6411	Approved
0.7714	Intermediate Similarity	NPD7902	Approved
0.7706	Intermediate Similarity	NPD6402	Approved
0.7706	Intermediate Similarity	NPD5739	Approved
0.7706	Intermediate Similarity	NPD7128	Approved
0.7706	Intermediate Similarity	NPD6675	Approved
0.7699	Intermediate Similarity	NPD4632	Approved
0.7686	Intermediate Similarity	NPD7319	Approved
0.7658	Intermediate Similarity	NPD6373	Approved
0.7658	Intermediate Similarity	NPD6372	Approved
0.7611	Intermediate Similarity	NPD8297	Approved
0.7603	Intermediate Similarity	NPD7736	Approved
0.7589	Intermediate Similarity	NPD4634	Approved
0.7583	Intermediate Similarity	NPD7507	Approved
0.7568	Intermediate Similarity	NPD7320	Approved
0.7568	Intermediate Similarity	NPD6899	Approved
0.7568	Intermediate Similarity	NPD6881	Approved
0.7549	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD6101	Approved
0.7522	Intermediate Similarity	NPD6650	Approved
0.7522	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD5779	Approved
0.75	Intermediate Similarity	NPD5778	Approved
0.75	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6399	Phase 3
0.75	Intermediate Similarity	NPD7115	Discovery
0.7477	Intermediate Similarity	NPD5701	Approved
0.7477	Intermediate Similarity	NPD5697	Approved
0.7477	Intermediate Similarity	NPD7638	Approved
0.7458	Intermediate Similarity	NPD6059	Approved
0.7458	Intermediate Similarity	NPD6054	Approved
0.7456	Intermediate Similarity	NPD6882	Approved
0.7438	Intermediate Similarity	NPD6616	Approved
0.7434	Intermediate Similarity	NPD6883	Approved
0.7434	Intermediate Similarity	NPD7290	Approved
0.7434	Intermediate Similarity	NPD7102	Approved
0.7429	Intermediate Similarity	NPD7900	Approved
0.7429	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7639	Approved
0.7407	Intermediate Similarity	NPD7640	Approved
0.7387	Intermediate Similarity	NPD6008	Approved
0.7383	Intermediate Similarity	NPD4755	Approved
0.7379	Intermediate Similarity	NPD5328	Approved
0.7377	Intermediate Similarity	NPD7078	Approved
0.7377	Intermediate Similarity	NPD8293	Discontinued
0.7368	Intermediate Similarity	NPD6847	Approved
0.7368	Intermediate Similarity	NPD8130	Phase 1
0.7368	Intermediate Similarity	NPD6617	Approved
0.7368	Intermediate Similarity	NPD6869	Approved
0.735	Intermediate Similarity	NPD6009	Approved
0.7345	Intermediate Similarity	NPD6014	Approved
0.7345	Intermediate Similarity	NPD6013	Approved
0.7345	Intermediate Similarity	NPD6012	Approved
0.7333	Intermediate Similarity	NPD6370	Approved
0.7327	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6412	Phase 2
0.7281	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6686	Approved
0.7257	Intermediate Similarity	NPD6011	Approved
0.725	Intermediate Similarity	NPD6015	Approved
0.725	Intermediate Similarity	NPD6016	Approved
0.725	Intermediate Similarity	NPD8517	Approved
0.725	Intermediate Similarity	NPD8515	Approved
0.725	Intermediate Similarity	NPD8516	Approved
0.725	Intermediate Similarity	NPD8513	Phase 3
0.725	Intermediate Similarity	NPD6921	Approved
0.7248	Intermediate Similarity	NPD5285	Approved
0.7248	Intermediate Similarity	NPD5286	Approved
0.7248	Intermediate Similarity	NPD4700	Approved
0.7248	Intermediate Similarity	NPD4696	Approved
0.7245	Intermediate Similarity	NPD7645	Phase 2
0.7241	Intermediate Similarity	NPD8133	Approved
0.7238	Intermediate Similarity	NPD6079	Approved
0.7238	Intermediate Similarity	NPD8035	Phase 2
0.7238	Intermediate Similarity	NPD8034	Phase 2
0.7238	Intermediate Similarity	NPD7983	Approved
0.7228	Intermediate Similarity	NPD4786	Approved
0.7217	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3667	Approved
0.719	Intermediate Similarity	NPD5988	Approved
0.7184	Intermediate Similarity	NPD3573	Approved
0.7156	Intermediate Similarity	NPD4225	Approved
0.7131	Intermediate Similarity	NPD7604	Phase 2
0.7117	Intermediate Similarity	NPD5225	Approved
0.7117	Intermediate Similarity	NPD4633	Approved
0.7117	Intermediate Similarity	NPD5224	Approved
0.7117	Intermediate Similarity	NPD5211	Phase 2
0.7117	Intermediate Similarity	NPD5226	Approved
0.7107	Intermediate Similarity	NPD5983	Phase 2
0.7087	Intermediate Similarity	NPD3618	Phase 1
0.7083	Intermediate Similarity	NPD7516	Approved
0.708	Intermediate Similarity	NPD4768	Approved
0.708	Intermediate Similarity	NPD4767	Approved
0.7064	Intermediate Similarity	NPD6083	Phase 2
0.7064	Intermediate Similarity	NPD6084	Phase 2
0.7054	Intermediate Similarity	NPD5174	Approved
0.7054	Intermediate Similarity	NPD5175	Approved
0.7027	Intermediate Similarity	NPD5223	Approved
0.7018	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6336	Discontinued
0.7009	Intermediate Similarity	NPD4202	Approved
0.7	Intermediate Similarity	NPD7328	Approved
0.7	Intermediate Similarity	NPD7525	Registered
0.7	Intermediate Similarity	NPD7327	Approved
0.6991	Remote Similarity	NPD5141	Approved
0.6975	Remote Similarity	NPD6274	Approved
0.6972	Remote Similarity	NPD5222	Approved
0.6972	Remote Similarity	NPD5221	Approved
0.6972	Remote Similarity	NPD4697	Phase 3
0.6972	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD8033	Approved
0.6957	Remote Similarity	NPD4729	Approved
0.6957	Remote Similarity	NPD4730	Approved
0.6952	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7100	Approved
0.6942	Remote Similarity	NPD7101	Approved
0.6909	Remote Similarity	NPD5173	Approved
0.6905	Remote Similarity	NPD6033	Approved
0.6903	Remote Similarity	NPD4754	Approved
0.6887	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8377	Approved
0.6885	Remote Similarity	NPD8294	Approved
0.6864	Remote Similarity	NPD6053	Discontinued
0.686	Remote Similarity	NPD6335	Approved
0.6838	Remote Similarity	NPD5250	Approved
0.6838	Remote Similarity	NPD5249	Phase 3
0.6838	Remote Similarity	NPD5247	Approved
0.6838	Remote Similarity	NPD5251	Approved
0.6838	Remote Similarity	NPD5248	Approved
0.6829	Remote Similarity	NPD8335	Approved
0.6829	Remote Similarity	NPD8296	Approved
0.6829	Remote Similarity	NPD8380	Approved
0.6829	Remote Similarity	NPD6909	Approved
0.6829	Remote Similarity	NPD8378	Approved
0.6829	Remote Similarity	NPD8379	Approved
0.6829	Remote Similarity	NPD6908	Approved
0.6825	Remote Similarity	NPD8074	Phase 3
0.6822	Remote Similarity	NPD46	Approved
0.6822	Remote Similarity	NPD6698	Approved
0.6814	Remote Similarity	NPD7632	Discontinued
0.681	Remote Similarity	NPD5128	Approved
0.68	Remote Similarity	NPD6114	Approved
0.68	Remote Similarity	NPD6115	Approved
0.68	Remote Similarity	NPD6118	Approved
0.68	Remote Similarity	NPD6697	Approved
0.6777	Remote Similarity	NPD6317	Approved
0.6762	Remote Similarity	NPD6684	Approved
0.6762	Remote Similarity	NPD7334	Approved
0.6762	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7146	Approved
0.6762	Remote Similarity	NPD6409	Approved
0.6762	Remote Similarity	NPD5330	Approved
0.6762	Remote Similarity	NPD7521	Approved
0.6759	Remote Similarity	NPD7637	Suspended
0.6731	Remote Similarity	NPD3668	Phase 3
0.6731	Remote Similarity	NPD3665	Phase 1
0.6731	Remote Similarity	NPD3666	Approved
0.6731	Remote Similarity	NPD3133	Approved
0.6729	Remote Similarity	NPD4753	Phase 2
0.6727	Remote Similarity	NPD5695	Phase 3
0.6726	Remote Similarity	NPD5344	Discontinued
0.6721	Remote Similarity	NPD6313	Approved
0.6721	Remote Similarity	NPD6314	Approved
0.67	Remote Similarity	NPD6116	Phase 1
0.6696	Remote Similarity	NPD5696	Approved
0.6694	Remote Similarity	NPD7503	Approved
0.6694	Remote Similarity	NPD6868	Approved
0.6639	Remote Similarity	NPD5216	Approved
0.6639	Remote Similarity	NPD5217	Approved
0.6639	Remote Similarity	NPD5215	Approved
0.6636	Remote Similarity	NPD5737	Approved
0.6636	Remote Similarity	NPD6903	Approved
0.6636	Remote Similarity	NPD6672	Approved
0.66	Remote Similarity	NPD6117	Approved
0.6577	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5135	Approved
0.6555	Remote Similarity	NPD6371	Approved
0.6555	Remote Similarity	NPD5169	Approved
0.6542	Remote Similarity	NPD7524	Approved
0.6518	Remote Similarity	NPD7839	Suspended
0.6518	Remote Similarity	NPD7614	Phase 1
0.6505	Remote Similarity	NPD4695	Discontinued
0.65	Remote Similarity	NPD6942	Approved
0.65	Remote Similarity	NPD3703	Phase 2
0.65	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5127	Approved
0.65	Remote Similarity	NPD7339	Approved
0.6486	Remote Similarity	NPD5282	Discontinued
0.6457	Remote Similarity	NPD6067	Discontinued
0.6455	Remote Similarity	NPD5281	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