NPASS Compound

Structure

NPC235889 OpenBabel07101719512D 36 40 0 0 1 0 0 0 0 0999 V2000 -4.8973 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2500 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6102 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9192 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9921 -2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7709 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6320 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 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 -2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3230 -3.0032 0.0000 C 0 0 2 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 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 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 -5.7709 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9629 -4.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3448 -2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 5 20 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 25 1 0 0 0 0 10 11 2 0 0 0 0 10 22 1 0 0 0 0 11 30 1 0 0 0 0 12 13 1 0 0 0 0 12 28 1 0 0 0 0 14 17 2 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 16 31 1 0 0 0 0 18 3 1 6 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 4 1 1 0 0 0 19 26 1 0 0 0 0 19 27 1 0 0 0 0 20 32 2 0 0 0 0 20 36 1 0 0 0 0 21 30 1 1 0 0 0 22 33 2 0 0 0 0 23 27 1 0 0 0 0 23 34 2 0 0 0 0 24 26 1 0 0 0 0 24 36 1 1 0 0 0 25 29 1 6 0 0 0 25 31 1 0 0 0 0 26 28 1 1 0 0 0 27 35 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 6 0 0 0 30 31 1 6 0 0 0 31 13 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.32
Volume:	532.719
LogP:	4.392
LogD:	3.933
LogS:	-5.351
# Rotatable Bonds:	7
TPSA:	77.51
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.346
Synthetic Accessibility Score:	5.946
Fsp3:	0.806
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.096
MDCK Permeability:	2.5536688553984277e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.07
30% Bioavailability (F30%):	0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232
Plasma Protein Binding (PPB):	95.60266876220703%
Volume Distribution (VD):	0.557
Pgp-substrate:	3.766345262527466%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.257
CYP2C19-inhibitor:	0.176
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.209
CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.909
CYP3A4-substrate:	0.743

ADMET: Excretion

Clearance (CL):	5.084
Half-life (T1/2):	0.148

ADMET: Toxicity

hERG Blockers:	0.489
Human Hepatotoxicity (H-HT):	0.363
Drug-inuced Liver Injury (DILI):	0.587
AMES Toxicity:	0.099
Rat Oral Acute Toxicity:	0.849
Maximum Recommended Daily Dose:	0.91
Skin Sensitization:	0.91
Carcinogencity:	0.827
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC235889

Natural Product ID:	NPC235889
*Common Name:**	LFOGMLHBIASASZ-CNWSIUGMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LFOGMLHBIASASZ-CNWSIUGMSA-N
Standard InCHI:	InChI=1S/C31H44O5/c1-17(2)14-23(34)27(35)19(4)26-24(36-20(5)32)15-29(7)25-9-8-21-18(3)22(33)10-11-30(21)16-31(25,30)13-12-28(26,29)6/h10-11,14,18-19,21,24-27,35H,8-9,12-13,15-16H2,1-7H3/t18-,19-,21-,24-,25-,26-,27+,28+,29-,30+,31-/m0/s1
SMILES:	CC(=CC(=O)[C@@H]([C@H]([C@H]1[C@@H](OC(=O)C)C[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)C=CC(=O)[C@H]2C)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1941164
PubChem CID:	57332506
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22168134]
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22206869]
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	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	2
Others	6

Activity Type	# Activity
Others	8

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	FC	=	53.0	n.a.	PMID[458474]
NPT2	Others	Unspecified	FC	=	5.2	n.a.	PMID[458474]
NPT2	Others	Unspecified	FC	=	1.1	n.a.	PMID[458474]
NPT2	Others	Unspecified	IC50	>	1000000.0	nM	PMID[458474]
NPT2	Others	Unspecified	FC	=	53.0	n.a.	PMID[458475]
NPT2	Others	Unspecified	FC	=	5.2	n.a.	PMID[458475]
NPT2	Others	Unspecified	FC	=	1.1	n.a.	PMID[458475]

☑ 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 NPC235889 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	199
0.1-0.2	1188
0.2-0.3	5169
0.3-0.4	11485
0.4-0.5	9692
0.5-0.6	6370
0.6-0.7	6259
0.7-0.8	2109
0.8-0.85	189
0.85-0.9	24
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC181265
0.96	High Similarity	NPC241927
0.96	High Similarity	NPC258543
0.9412	High Similarity	NPC214797
0.9412	High Similarity	NPC118860
0.9412	High Similarity	NPC231589
0.9388	High Similarity	NPC308351
0.9388	High Similarity	NPC271266
0.932	High Similarity	NPC71348
0.932	High Similarity	NPC170487
0.9109	High Similarity	NPC470267
0.9057	High Similarity	NPC270958
0.902	High Similarity	NPC44063
0.8932	High Similarity	NPC470269
0.8889	High Similarity	NPC118638
0.8868	High Similarity	NPC202889
0.8846	High Similarity	NPC2766
0.8835	High Similarity	NPC475294
0.8812	High Similarity	NPC15396
0.8776	High Similarity	NPC469599
0.8774	High Similarity	NPC100267
0.8774	High Similarity	NPC475524
0.8763	High Similarity	NPC109414
0.8762	High Similarity	NPC197428
0.8738	High Similarity	NPC470309
0.87	High Similarity	NPC197386
0.866	High Similarity	NPC154101
0.8641	High Similarity	NPC310586
0.8627	High Similarity	NPC87351
0.8614	High Similarity	NPC144956
0.8598	High Similarity	NPC221144
0.8571	High Similarity	NPC94529
0.8558	High Similarity	NPC265127
0.8544	High Similarity	NPC311612
0.8544	High Similarity	NPC236390
0.8532	High Similarity	NPC148458
0.8529	High Similarity	NPC476223
0.8529	High Similarity	NPC474327
0.8529	High Similarity	NPC476240
0.8529	High Similarity	NPC224720
0.8515	High Similarity	NPC222011
0.8515	High Similarity	NPC98868
0.8515	High Similarity	NPC114274
0.8505	High Similarity	NPC43775
0.85	High Similarity	NPC305483
0.85	High Similarity	NPC328162
0.85	High Similarity	NPC96859
0.8491	Intermediate Similarity	NPC304495
0.8485	Intermediate Similarity	NPC294266
0.8469	Intermediate Similarity	NPC218301
0.8462	Intermediate Similarity	NPC255309
0.8462	Intermediate Similarity	NPC29705
0.8462	Intermediate Similarity	NPC137657
0.8455	Intermediate Similarity	NPC471854
0.8455	Intermediate Similarity	NPC239273
0.8454	Intermediate Similarity	NPC477943
0.8447	Intermediate Similarity	NPC195290
0.8447	Intermediate Similarity	NPC136289
0.8447	Intermediate Similarity	NPC308726
0.8447	Intermediate Similarity	NPC119601
0.8447	Intermediate Similarity	NPC473928
0.8447	Intermediate Similarity	NPC204450
0.8431	Intermediate Similarity	NPC218383
0.8431	Intermediate Similarity	NPC476274
0.8416	Intermediate Similarity	NPC87090
0.8416	Intermediate Similarity	NPC18319
0.8416	Intermediate Similarity	NPC107243
0.8416	Intermediate Similarity	NPC43747
0.8416	Intermediate Similarity	NPC108078
0.8416	Intermediate Similarity	NPC57416
0.8416	Intermediate Similarity	NPC69385
0.8416	Intermediate Similarity	NPC18509
0.84	Intermediate Similarity	NPC476174
0.84	Intermediate Similarity	NPC470016
0.84	Intermediate Similarity	NPC317586
0.8396	Intermediate Similarity	NPC211224
0.8384	Intermediate Similarity	NPC206810
0.8384	Intermediate Similarity	NPC25750
0.8381	Intermediate Similarity	NPC96377
0.8381	Intermediate Similarity	NPC278628
0.8381	Intermediate Similarity	NPC196528
0.8381	Intermediate Similarity	NPC231530
0.8378	Intermediate Similarity	NPC257457
0.8378	Intermediate Similarity	NPC311554
0.8365	Intermediate Similarity	NPC140723
0.8365	Intermediate Similarity	NPC111323
0.835	Intermediate Similarity	NPC81530
0.835	Intermediate Similarity	NPC99411
0.835	Intermediate Similarity	NPC163372
0.835	Intermediate Similarity	NPC302537
0.835	Intermediate Similarity	NPC477356
0.8333	Intermediate Similarity	NPC176845
0.8333	Intermediate Similarity	NPC327115
0.8333	Intermediate Similarity	NPC235464
0.8333	Intermediate Similarity	NPC166745
0.8333	Intermediate Similarity	NPC147954
0.8333	Intermediate Similarity	NPC477355
0.8333	Intermediate Similarity	NPC477854
0.8333	Intermediate Similarity	NPC195640
0.8317	Intermediate Similarity	NPC42042
0.8317	Intermediate Similarity	NPC111684
0.8317	Intermediate Similarity	NPC328371
0.8317	Intermediate Similarity	NPC58052
0.8317	Intermediate Similarity	NPC125622
0.8302	Intermediate Similarity	NPC185
0.83	Intermediate Similarity	NPC166906
0.8286	Intermediate Similarity	NPC13385
0.8283	Intermediate Similarity	NPC185936
0.8283	Intermediate Similarity	NPC168027
0.8273	Intermediate Similarity	NPC471398
0.8269	Intermediate Similarity	NPC22388
0.8269	Intermediate Similarity	NPC56498
0.8269	Intermediate Similarity	NPC118405
0.8265	Intermediate Similarity	NPC326627
0.8265	Intermediate Similarity	NPC305039
0.8265	Intermediate Similarity	NPC76879
0.8265	Intermediate Similarity	NPC54689
0.8265	Intermediate Similarity	NPC310010
0.8252	Intermediate Similarity	NPC205899
0.8252	Intermediate Similarity	NPC15390
0.8252	Intermediate Similarity	NPC474720
0.8247	Intermediate Similarity	NPC58063
0.8235	Intermediate Similarity	NPC475894
0.8229	Intermediate Similarity	NPC29447
0.8229	Intermediate Similarity	NPC469948
0.8229	Intermediate Similarity	NPC323765
0.8224	Intermediate Similarity	NPC469844
0.8218	Intermediate Similarity	NPC472932
0.8218	Intermediate Similarity	NPC318282
0.8218	Intermediate Similarity	NPC33473
0.8218	Intermediate Similarity	NPC241156
0.8218	Intermediate Similarity	NPC173875
0.8218	Intermediate Similarity	NPC174948
0.8218	Intermediate Similarity	NPC469995
0.82	Intermediate Similarity	NPC12722
0.82	Intermediate Similarity	NPC474807
0.82	Intermediate Similarity	NPC66429
0.82	Intermediate Similarity	NPC470376
0.82	Intermediate Similarity	NPC470375
0.82	Intermediate Similarity	NPC79117
0.82	Intermediate Similarity	NPC152897
0.819	Intermediate Similarity	NPC264048
0.819	Intermediate Similarity	NPC474207
0.819	Intermediate Similarity	NPC470310
0.819	Intermediate Similarity	NPC474330
0.8182	Intermediate Similarity	NPC194100
0.8173	Intermediate Similarity	NPC310981
0.8165	Intermediate Similarity	NPC470281
0.8163	Intermediate Similarity	NPC294480
0.8155	Intermediate Similarity	NPC10364
0.8148	Intermediate Similarity	NPC214644
0.8148	Intermediate Similarity	NPC41405
0.8144	Intermediate Similarity	NPC474732
0.8144	Intermediate Similarity	NPC51014
0.8144	Intermediate Similarity	NPC31564
0.8144	Intermediate Similarity	NPC145879
0.8144	Intermediate Similarity	NPC474778
0.8144	Intermediate Similarity	NPC474733
0.8144	Intermediate Similarity	NPC155011
0.8144	Intermediate Similarity	NPC20688
0.8142	Intermediate Similarity	NPC61520
0.8137	Intermediate Similarity	NPC471039
0.8137	Intermediate Similarity	NPC29152
0.8137	Intermediate Similarity	NPC477853
0.8137	Intermediate Similarity	NPC95565
0.8137	Intermediate Similarity	NPC173272
0.8137	Intermediate Similarity	NPC49371
0.8131	Intermediate Similarity	NPC220974
0.8131	Intermediate Similarity	NPC472925
0.8125	Intermediate Similarity	NPC227064
0.8125	Intermediate Similarity	NPC82902
0.8125	Intermediate Similarity	NPC237712
0.8125	Intermediate Similarity	NPC329043
0.8125	Intermediate Similarity	NPC214043
0.8125	Intermediate Similarity	NPC321187
0.8125	Intermediate Similarity	NPC85774
0.8125	Intermediate Similarity	NPC58841
0.8125	Intermediate Similarity	NPC161423
0.8119	Intermediate Similarity	NPC196485
0.8119	Intermediate Similarity	NPC184870
0.8119	Intermediate Similarity	NPC111015
0.8119	Intermediate Similarity	NPC245972
0.8119	Intermediate Similarity	NPC124207
0.8113	Intermediate Similarity	NPC96268
0.8113	Intermediate Similarity	NPC164835
0.8113	Intermediate Similarity	NPC228669
0.81	Intermediate Similarity	NPC470113
0.81	Intermediate Similarity	NPC476187
0.8095	Intermediate Similarity	NPC473163
0.8091	Intermediate Similarity	NPC280782
0.8091	Intermediate Similarity	NPC264634
0.8081	Intermediate Similarity	NPC262043
0.8081	Intermediate Similarity	NPC66344
0.8081	Intermediate Similarity	NPC31985
0.8081	Intermediate Similarity	NPC186688
0.8081	Intermediate Similarity	NPC474570
0.8081	Intermediate Similarity	NPC476733
0.8081	Intermediate Similarity	NPC474245
0.8081	Intermediate Similarity	NPC1015
0.8081	Intermediate Similarity	NPC215029

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 NPC235889 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1414
0.2-0.3	3892
0.3-0.4	2466
0.4-0.5	692
0.5-0.6	188
0.6-0.7	156
0.7-0.8	97
0.8-0.85	52
0.85-0.9	29
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9118	High Similarity	NPD6899	Approved
0.9118	High Similarity	NPD6881	Approved
0.902	High Similarity	NPD5697	Approved
0.8942	High Similarity	NPD6883	Approved
0.8942	High Similarity	NPD7102	Approved
0.8942	High Similarity	NPD7290	Approved
0.8932	High Similarity	NPD6011	Approved
0.8922	High Similarity	NPD6402	Approved
0.8922	High Similarity	NPD7128	Approved
0.8922	High Similarity	NPD6675	Approved
0.8922	High Similarity	NPD5739	Approved
0.8857	High Similarity	NPD6617	Approved
0.8857	High Similarity	NPD6650	Approved
0.8857	High Similarity	NPD6869	Approved
0.8857	High Similarity	NPD6649	Approved
0.8857	High Similarity	NPD6847	Approved
0.8857	High Similarity	NPD8130	Phase 1
0.8846	High Similarity	NPD6013	Approved
0.8846	High Similarity	NPD6012	Approved
0.8846	High Similarity	NPD6014	Approved
0.8788	High Similarity	NPD6083	Phase 2
0.8788	High Similarity	NPD6084	Phase 2
0.8774	High Similarity	NPD6882	Approved
0.8774	High Similarity	NPD8297	Approved
0.875	High Similarity	NPD7320	Approved
0.8667	High Similarity	NPD6372	Approved
0.8667	High Similarity	NPD6373	Approved
0.8654	High Similarity	NPD5701	Approved
0.8614	High Similarity	NPD5286	Approved
0.8614	High Similarity	NPD5285	Approved
0.8614	High Similarity	NPD4696	Approved
0.8529	High Similarity	NPD5223	Approved
0.8505	High Similarity	NPD6401	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD5224	Approved
0.8447	Intermediate Similarity	NPD5226	Approved
0.8447	Intermediate Similarity	NPD5225	Approved
0.8447	Intermediate Similarity	NPD5211	Phase 2
0.8447	Intermediate Similarity	NPD4633	Approved
0.8416	Intermediate Similarity	NPD4755	Approved
0.84	Intermediate Similarity	NPD5695	Phase 3
0.8384	Intermediate Similarity	NPD6399	Phase 3
0.8378	Intermediate Similarity	NPD6335	Approved
0.8365	Intermediate Similarity	NPD5174	Approved
0.8365	Intermediate Similarity	NPD5175	Approved
0.8351	Intermediate Similarity	NPD6672	Approved
0.8351	Intermediate Similarity	NPD5737	Approved
0.8349	Intermediate Similarity	NPD4632	Approved
0.8333	Intermediate Similarity	NPD7334	Approved
0.8333	Intermediate Similarity	NPD6684	Approved
0.8333	Intermediate Similarity	NPD7521	Approved
0.8333	Intermediate Similarity	NPD5696	Approved
0.8333	Intermediate Similarity	NPD6409	Approved
0.8333	Intermediate Similarity	NPD5330	Approved
0.8333	Intermediate Similarity	NPD7604	Phase 2
0.8333	Intermediate Similarity	NPD7146	Approved
0.8317	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8317	Intermediate Similarity	NPD5222	Approved
0.8317	Intermediate Similarity	NPD5221	Approved
0.8304	Intermediate Similarity	NPD7101	Approved
0.8304	Intermediate Similarity	NPD7100	Approved
0.8288	Intermediate Similarity	NPD6317	Approved
0.8286	Intermediate Similarity	NPD5141	Approved
0.8283	Intermediate Similarity	NPD6079	Approved
0.8265	Intermediate Similarity	NPD6904	Approved
0.8265	Intermediate Similarity	NPD4753	Phase 2
0.8265	Intermediate Similarity	NPD6673	Approved
0.8265	Intermediate Similarity	NPD6080	Approved
0.8252	Intermediate Similarity	NPD4700	Approved
0.8235	Intermediate Similarity	NPD5173	Approved
0.8218	Intermediate Similarity	NPD4629	Approved
0.8218	Intermediate Similarity	NPD5210	Approved
0.8214	Intermediate Similarity	NPD6314	Approved
0.8214	Intermediate Similarity	NPD6313	Approved
0.8198	Intermediate Similarity	NPD6274	Approved
0.8163	Intermediate Similarity	NPD6903	Approved
0.8163	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3133	Approved
0.8125	Intermediate Similarity	NPD3665	Phase 1
0.8125	Intermediate Similarity	NPD6009	Approved
0.8125	Intermediate Similarity	NPD3666	Approved
0.8081	Intermediate Similarity	NPD5328	Approved
0.807	Intermediate Similarity	NPD6319	Approved
0.8056	Intermediate Similarity	NPD4729	Approved
0.8056	Intermediate Similarity	NPD4730	Approved
0.8041	Intermediate Similarity	NPD5329	Approved
0.8039	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6008	Approved
0.8036	Intermediate Similarity	NPD6868	Approved
0.8019	Intermediate Similarity	NPD4754	Approved
0.8	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5983	Phase 2
0.7961	Intermediate Similarity	NPD4697	Phase 3
0.7959	Intermediate Similarity	NPD5690	Phase 2
0.7959	Intermediate Similarity	NPD6098	Approved
0.7949	Intermediate Similarity	NPD7492	Approved
0.7938	Intermediate Similarity	NPD4786	Approved
0.7938	Intermediate Similarity	NPD4197	Approved
0.7921	Intermediate Similarity	NPD5694	Approved
0.7921	Intermediate Similarity	NPD5281	Approved
0.7921	Intermediate Similarity	NPD5284	Approved
0.7921	Intermediate Similarity	NPD5693	Phase 1
0.7921	Intermediate Similarity	NPD6050	Approved
0.7913	Intermediate Similarity	NPD6054	Approved
0.7909	Intermediate Similarity	NPD5249	Phase 3
0.7909	Intermediate Similarity	NPD5248	Approved
0.7909	Intermediate Similarity	NPD5250	Approved
0.7909	Intermediate Similarity	NPD5169	Approved
0.7909	Intermediate Similarity	NPD5251	Approved
0.7909	Intermediate Similarity	NPD5247	Approved
0.7909	Intermediate Similarity	NPD5135	Approved
0.7909	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD4634	Approved
0.789	Intermediate Similarity	NPD5128	Approved
0.7881	Intermediate Similarity	NPD6616	Approved
0.7881	Intermediate Similarity	NPD6336	Discontinued
0.787	Intermediate Similarity	NPD4767	Approved
0.787	Intermediate Similarity	NPD4768	Approved
0.7845	Intermediate Similarity	NPD6909	Approved
0.7845	Intermediate Similarity	NPD6908	Approved
0.7843	Intermediate Similarity	NPD4202	Approved
0.7838	Intermediate Similarity	NPD5217	Approved
0.7838	Intermediate Similarity	NPD5216	Approved
0.7838	Intermediate Similarity	NPD5127	Approved
0.7838	Intermediate Similarity	NPD5215	Approved
0.7822	Intermediate Similarity	NPD5692	Phase 3
0.7815	Intermediate Similarity	NPD7078	Approved
0.7778	Intermediate Similarity	NPD5279	Phase 3
0.7778	Intermediate Similarity	NPD6370	Approved
0.775	Intermediate Similarity	NPD7736	Approved
0.7732	Intermediate Similarity	NPD3667	Approved
0.7732	Intermediate Similarity	NPD4223	Phase 3
0.7732	Intermediate Similarity	NPD4221	Approved
0.7692	Intermediate Similarity	NPD6016	Approved
0.7692	Intermediate Similarity	NPD6015	Approved
0.7652	Intermediate Similarity	NPD7115	Discovery
0.7636	Intermediate Similarity	NPD6412	Phase 2
0.7632	Intermediate Similarity	NPD5167	Approved
0.7627	Intermediate Similarity	NPD5988	Approved
0.7624	Intermediate Similarity	NPD5208	Approved
0.7607	Intermediate Similarity	NPD6059	Approved
0.76	Intermediate Similarity	NPD5280	Approved
0.76	Intermediate Similarity	NPD4694	Approved
0.76	Intermediate Similarity	NPD3618	Phase 1
0.7596	Intermediate Similarity	NPD6001	Approved
0.7596	Intermediate Similarity	NPD7748	Approved
0.7573	Intermediate Similarity	NPD7515	Phase 2
0.7568	Intermediate Similarity	NPD5168	Approved
0.7551	Intermediate Similarity	NPD6435	Approved
0.7547	Intermediate Similarity	NPD7902	Approved
0.7547	Intermediate Similarity	NPD5959	Approved
0.7526	Intermediate Similarity	NPD4695	Discontinued
0.7521	Intermediate Similarity	NPD8293	Discontinued
0.7477	Intermediate Similarity	NPD6614	Approved
0.7477	Intermediate Similarity	NPD7638	Approved
0.7476	Intermediate Similarity	NPD5207	Approved
0.7475	Intermediate Similarity	NPD4788	Approved
0.7456	Intermediate Similarity	NPD6053	Discontinued
0.7426	Intermediate Similarity	NPD4689	Approved
0.7426	Intermediate Similarity	NPD4138	Approved
0.7426	Intermediate Similarity	NPD4688	Approved
0.7426	Intermediate Similarity	NPD4690	Approved
0.7426	Intermediate Similarity	NPD4693	Phase 3
0.7426	Intermediate Similarity	NPD5205	Approved
0.7423	Intermediate Similarity	NPD4195	Approved
0.7407	Intermediate Similarity	NPD7640	Approved
0.7407	Intermediate Similarity	NPD7639	Approved
0.7404	Intermediate Similarity	NPD6411	Approved
0.7379	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5654	Approved
0.7353	Intermediate Similarity	NPD3573	Approved
0.7347	Intermediate Similarity	NPD5368	Approved
0.7333	Intermediate Similarity	NPD5133	Approved
0.732	Intermediate Similarity	NPD3617	Approved
0.7308	Intermediate Similarity	NPD5785	Approved
0.7273	Intermediate Similarity	NPD5091	Approved
0.7264	Intermediate Similarity	NPD7900	Approved
0.7264	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8035	Phase 2
0.7238	Intermediate Similarity	NPD8034	Phase 2
0.7228	Intermediate Similarity	NPD3668	Phase 3
0.7212	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6101	Approved
0.7177	Intermediate Similarity	NPD6033	Approved
0.7157	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5363	Approved
0.7129	Intermediate Similarity	NPD5362	Discontinued
0.7113	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5369	Approved
0.7087	Intermediate Similarity	NPD5786	Approved
0.7083	Intermediate Similarity	NPD4522	Approved
0.7077	Intermediate Similarity	NPD6334	Approved
0.7077	Intermediate Similarity	NPD6333	Approved
0.7054	Intermediate Similarity	NPD6052	Approved
0.7048	Intermediate Similarity	NPD6051	Approved
0.7037	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7507	Approved
0.701	Intermediate Similarity	NPD6942	Approved
0.701	Intermediate Similarity	NPD7339	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