NPASS Compound

Structure

NPC220974 OpenBabel07101719512D 39 43 0 0 1 0 0 0 0 0999 V2000 1.9501 -6.4575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2372 -5.2985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 2.8660 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 1.5899 -4.7633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2298 -3.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2591 -5.5064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8990 -3.8122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.1180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 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 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4899 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8771 -3.6043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2989 -2.3968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 -0.8090 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 3 18 1 0 0 0 0 5 30 1 0 0 0 0 8 9 1 0 0 0 0 8 22 2 0 0 0 0 9 24 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 17 2 0 0 0 0 14 19 1 0 0 0 0 15 19 1 0 0 0 0 16 31 1 0 0 0 0 18 33 2 0 0 0 0 18 38 1 0 0 0 0 19 34 2 0 0 0 0 20 15 1 6 0 0 0 20 26 1 0 0 0 0 20 27 1 0 0 0 0 21 22 1 0 0 0 0 21 29 1 6 0 0 0 22 31 1 0 0 0 0 23 16 1 6 0 0 0 23 26 1 0 0 0 0 23 39 1 0 0 0 0 24 29 1 6 0 0 0 24 32 1 0 0 0 0 25 32 1 1 0 0 0 25 38 1 0 0 0 0 26 30 1 1 0 0 0 27 35 2 0 0 0 0 27 39 1 0 0 0 0 28 32 1 0 0 0 0 28 36 2 0 0 0 0 28 37 1 0 0 0 0 29 4 1 6 0 0 0 30 31 1 1 0 0 0 31 6 1 6 0 0 0 32 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.31
Volume:	564.959
LogP:	4.396
LogD:	3.356
LogS:	-4.037
# Rotatable Bonds:	7
TPSA:	114.04
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	5.124
Fsp3:	0.719
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:	-5.469
MDCK Permeability:	2.829037475748919e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.072
30% Bioavailability (F30%):	0.163

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.486
Plasma Protein Binding (PPB):	94.80982208251953%
Volume Distribution (VD):	0.432
Pgp-substrate:	4.307297706604004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.755
CYP2C9-inhibitor:	0.362
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.16
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	2.047
Half-life (T1/2):	0.81

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.889
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.836
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.172
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.139
Respiratory Toxicity:	0.187

Download Data

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

Natural Product: NPC220974

Natural Product ID:	NPC220974
*Common Name:**	FILHRDIXAYLUHH-XTURJDPMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FILHRDIXAYLUHH-XTURJDPMSA-N
Standard InCHI:	InChI=1S/C32H44O7/c1-17(2)14-19(34)15-20-26-23(39-27(20)35)16-31(6)22-8-9-24-29(4,21(22)10-13-30(26,31)5)12-11-25(38-18(3)33)32(24,7)28(36)37/h8,14,20-21,23-26H,9-13,15-16H2,1-7H3,(H,36,37)/t20-,21+,23+,24-,25-,26-,29-,30+,31-,32+/m1/s1
SMILES:	CC(=CC(=O)C[C@@H]1[C@@H]2[C@H](C[C@]3(C)C4=CC[C@@H]5[C@](C)(CC[C@H]([C@@]5(C)C(=O)O)OC(=O)C)[C@H]4CC[C@@]23C)OC1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503000
PubChem CID:	10674014
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[10869197]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812212]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9834145]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1859	Lantana camara	Species	Verbenaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT670	Individual Protein	Thrombin	Homo sapiens	IC50	=	18.0	nM	PMID[463810]

☑ 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 NPC220974 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	216
0.1-0.2	1334
0.2-0.3	5329
0.3-0.4	10520
0.4-0.5	10617
0.5-0.6	6324
0.6-0.7	5793
0.7-0.8	2391
0.8-0.85	154
0.85-0.9	16
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9423	High Similarity	NPC52634
0.93	High Similarity	NPC36321
0.8738	High Similarity	NPC140723
0.8725	High Similarity	NPC473514
0.8692	High Similarity	NPC43775
0.8687	High Similarity	NPC159410
0.8641	High Similarity	NPC22388
0.86	High Similarity	NPC473648
0.86	High Similarity	NPC469599
0.8586	High Similarity	NPC470224
0.8571	High Similarity	NPC471896
0.8558	High Similarity	NPC470310
0.8522	High Similarity	NPC174367
0.8522	High Similarity	NPC47113
0.8515	High Similarity	NPC327788
0.8515	High Similarity	NPC95565
0.8505	High Similarity	NPC475941
0.8505	High Similarity	NPC474901
0.8491	Intermediate Similarity	NPC44063
0.8476	Intermediate Similarity	NPC471293
0.8469	Intermediate Similarity	NPC474570
0.8447	Intermediate Similarity	NPC475392
0.8447	Intermediate Similarity	NPC475385
0.8447	Intermediate Similarity	NPC475202
0.844	Intermediate Similarity	NPC71348
0.8431	Intermediate Similarity	NPC292133
0.8431	Intermediate Similarity	NPC26413
0.8431	Intermediate Similarity	NPC23680
0.8431	Intermediate Similarity	NPC475894
0.8426	Intermediate Similarity	NPC197428
0.8416	Intermediate Similarity	NPC317586
0.8416	Intermediate Similarity	NPC184848
0.8416	Intermediate Similarity	NPC69548
0.8416	Intermediate Similarity	NPC470016
0.84	Intermediate Similarity	NPC470376
0.84	Intermediate Similarity	NPC141497
0.84	Intermediate Similarity	NPC107674
0.84	Intermediate Similarity	NPC470375
0.84	Intermediate Similarity	NPC170220
0.8396	Intermediate Similarity	NPC196528
0.8396	Intermediate Similarity	NPC231530
0.8396	Intermediate Similarity	NPC278628
0.8384	Intermediate Similarity	NPC111585
0.8384	Intermediate Similarity	NPC148414
0.8384	Intermediate Similarity	NPC175628
0.8381	Intermediate Similarity	NPC236390
0.8381	Intermediate Similarity	NPC312900
0.8378	Intermediate Similarity	NPC266728
0.8378	Intermediate Similarity	NPC49492
0.8367	Intermediate Similarity	NPC28227
0.835	Intermediate Similarity	NPC477813
0.835	Intermediate Similarity	NPC271387
0.835	Intermediate Similarity	NPC176845
0.835	Intermediate Similarity	NPC153792
0.8333	Intermediate Similarity	NPC470921
0.8333	Intermediate Similarity	NPC2766
0.8333	Intermediate Similarity	NPC120708
0.8333	Intermediate Similarity	NPC13949
0.8333	Intermediate Similarity	NPC471153
0.8317	Intermediate Similarity	NPC166906
0.8317	Intermediate Similarity	NPC471078
0.8317	Intermediate Similarity	NPC473280
0.8317	Intermediate Similarity	NPC473435
0.8317	Intermediate Similarity	NPC473431
0.8304	Intermediate Similarity	NPC239273
0.8304	Intermediate Similarity	NPC471854
0.8302	Intermediate Similarity	NPC255309
0.8302	Intermediate Similarity	NPC96268
0.8302	Intermediate Similarity	NPC472227
0.8302	Intermediate Similarity	NPC472228
0.83	Intermediate Similarity	NPC110657
0.83	Intermediate Similarity	NPC86266
0.83	Intermediate Similarity	NPC297265
0.83	Intermediate Similarity	NPC26888
0.83	Intermediate Similarity	NPC212301
0.83	Intermediate Similarity	NPC154101
0.8286	Intermediate Similarity	NPC136289
0.8286	Intermediate Similarity	NPC473928
0.8286	Intermediate Similarity	NPC204450
0.8286	Intermediate Similarity	NPC193934
0.8286	Intermediate Similarity	NPC271980
0.8286	Intermediate Similarity	NPC56498
0.8286	Intermediate Similarity	NPC195290
0.8283	Intermediate Similarity	NPC477943
0.8283	Intermediate Similarity	NPC475921
0.8283	Intermediate Similarity	NPC474889
0.8283	Intermediate Similarity	NPC474704
0.8273	Intermediate Similarity	NPC207251
0.8273	Intermediate Similarity	NPC280782
0.8273	Intermediate Similarity	NPC100267
0.8273	Intermediate Similarity	NPC475524
0.8273	Intermediate Similarity	NPC475970
0.8269	Intermediate Similarity	NPC476274
0.8269	Intermediate Similarity	NPC35751
0.8269	Intermediate Similarity	NPC477521
0.8265	Intermediate Similarity	NPC167877
0.8257	Intermediate Similarity	NPC5284
0.8252	Intermediate Similarity	NPC226986
0.8252	Intermediate Similarity	NPC89225
0.8252	Intermediate Similarity	NPC18509
0.8241	Intermediate Similarity	NPC469844
0.8241	Intermediate Similarity	NPC94529
0.8235	Intermediate Similarity	NPC88310
0.8235	Intermediate Similarity	NPC255809
0.8235	Intermediate Similarity	NPC210214
0.823	Intermediate Similarity	NPC257457
0.823	Intermediate Similarity	NPC329736
0.823	Intermediate Similarity	NPC311554
0.8224	Intermediate Similarity	NPC96377
0.8224	Intermediate Similarity	NPC181265
0.8224	Intermediate Similarity	NPC60681
0.8224	Intermediate Similarity	NPC265127
0.8218	Intermediate Similarity	NPC294263
0.8218	Intermediate Similarity	NPC25750
0.8214	Intermediate Similarity	NPC72772
0.8214	Intermediate Similarity	NPC469794
0.8214	Intermediate Similarity	NPC270958
0.8208	Intermediate Similarity	NPC159442
0.8208	Intermediate Similarity	NPC180204
0.8208	Intermediate Similarity	NPC72151
0.8198	Intermediate Similarity	NPC962
0.8198	Intermediate Similarity	NPC472929
0.8198	Intermediate Similarity	NPC202889
0.8198	Intermediate Similarity	NPC250109
0.819	Intermediate Similarity	NPC474327
0.819	Intermediate Similarity	NPC52899
0.819	Intermediate Similarity	NPC81530
0.819	Intermediate Similarity	NPC476240
0.819	Intermediate Similarity	NPC476223
0.819	Intermediate Similarity	NPC289148
0.819	Intermediate Similarity	NPC163963
0.819	Intermediate Similarity	NPC224720
0.8182	Intermediate Similarity	NPC328539
0.8173	Intermediate Similarity	NPC164349
0.8173	Intermediate Similarity	NPC114274
0.8173	Intermediate Similarity	NPC477854
0.8165	Intermediate Similarity	NPC258543
0.8165	Intermediate Similarity	NPC304495
0.8165	Intermediate Similarity	NPC241927
0.8163	Intermediate Similarity	NPC195640
0.8158	Intermediate Similarity	NPC61520
0.8155	Intermediate Similarity	NPC472806
0.8155	Intermediate Similarity	NPC305483
0.8155	Intermediate Similarity	NPC173272
0.8155	Intermediate Similarity	NPC96859
0.8155	Intermediate Similarity	NPC167193
0.8155	Intermediate Similarity	NPC125622
0.8155	Intermediate Similarity	NPC42042
0.8155	Intermediate Similarity	NPC328162
0.8155	Intermediate Similarity	NPC322063
0.8155	Intermediate Similarity	NPC98874
0.8155	Intermediate Similarity	NPC192428
0.8148	Intermediate Similarity	NPC59530
0.8148	Intermediate Similarity	NPC473037
0.8142	Intermediate Similarity	NPC470959
0.8142	Intermediate Similarity	NPC476965
0.8142	Intermediate Similarity	NPC472934
0.8137	Intermediate Similarity	NPC49670
0.8137	Intermediate Similarity	NPC78580
0.8137	Intermediate Similarity	NPC74751
0.8137	Intermediate Similarity	NPC111015
0.8137	Intermediate Similarity	NPC124207
0.8137	Intermediate Similarity	NPC184006
0.8137	Intermediate Similarity	NPC23621
0.8131	Intermediate Similarity	NPC235889
0.8131	Intermediate Similarity	NPC29705
0.8131	Intermediate Similarity	NPC470251
0.8131	Intermediate Similarity	NPC98603
0.8131	Intermediate Similarity	NPC135854
0.8131	Intermediate Similarity	NPC137657
0.8131	Intermediate Similarity	NPC2436
0.8131	Intermediate Similarity	NPC164835
0.8131	Intermediate Similarity	NPC216245
0.8131	Intermediate Similarity	NPC189616
0.8131	Intermediate Similarity	NPC228669
0.8131	Intermediate Similarity	NPC28656
0.8125	Intermediate Similarity	NPC326542
0.8119	Intermediate Similarity	NPC168027
0.8119	Intermediate Similarity	NPC23434
0.8119	Intermediate Similarity	NPC185936
0.8119	Intermediate Similarity	NPC250753
0.8119	Intermediate Similarity	NPC471901
0.8119	Intermediate Similarity	NPC150383
0.8113	Intermediate Similarity	NPC477915
0.8113	Intermediate Similarity	NPC88203
0.8113	Intermediate Similarity	NPC76866
0.8113	Intermediate Similarity	NPC53222
0.8113	Intermediate Similarity	NPC320447
0.8113	Intermediate Similarity	NPC304832
0.8113	Intermediate Similarity	NPC148628
0.8113	Intermediate Similarity	NPC475558
0.8113	Intermediate Similarity	NPC246736
0.8113	Intermediate Similarity	NPC214946
0.8113	Intermediate Similarity	NPC286519
0.8113	Intermediate Similarity	NPC124544
0.8113	Intermediate Similarity	NPC473788
0.8108	Intermediate Similarity	NPC69291
0.8108	Intermediate Similarity	NPC264634
0.8108	Intermediate Similarity	NPC285956
0.8108	Intermediate Similarity	NPC476163

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 NPC220974 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1617
0.2-0.3	4081
0.3-0.4	2180
0.4-0.5	609
0.5-0.6	172
0.6-0.7	142
0.7-0.8	110
0.8-0.85	50
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8857	High Similarity	NPD6373	Approved
0.8857	High Similarity	NPD6372	Approved
0.8762	High Similarity	NPD7320	Approved
0.875	High Similarity	NPD6675	Approved
0.875	High Similarity	NPD7128	Approved
0.875	High Similarity	NPD5739	Approved
0.875	High Similarity	NPD6402	Approved
0.8692	High Similarity	NPD6650	Approved
0.8692	High Similarity	NPD6649	Approved
0.8585	High Similarity	NPD6881	Approved
0.8585	High Similarity	NPD6899	Approved
0.8519	High Similarity	NPD8130	Phase 1
0.8491	Intermediate Similarity	NPD5701	Approved
0.8491	Intermediate Similarity	NPD5697	Approved
0.844	Intermediate Similarity	NPD8297	Approved
0.8426	Intermediate Similarity	NPD7290	Approved
0.8426	Intermediate Similarity	NPD7102	Approved
0.8426	Intermediate Similarity	NPD6883	Approved
0.8416	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD6399	Phase 3
0.8396	Intermediate Similarity	NPD6008	Approved
0.8349	Intermediate Similarity	NPD6847	Approved
0.8349	Intermediate Similarity	NPD6617	Approved
0.8349	Intermediate Similarity	NPD6869	Approved
0.8333	Intermediate Similarity	NPD6013	Approved
0.8333	Intermediate Similarity	NPD6012	Approved
0.8333	Intermediate Similarity	NPD6014	Approved
0.8283	Intermediate Similarity	NPD5328	Approved
0.8273	Intermediate Similarity	NPD6882	Approved
0.8252	Intermediate Similarity	NPD6083	Phase 2
0.8252	Intermediate Similarity	NPD6084	Phase 2
0.8252	Intermediate Similarity	NPD4755	Approved
0.8252	Intermediate Similarity	NPD7902	Approved
0.8241	Intermediate Similarity	NPD6011	Approved
0.8182	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6903	Approved
0.8173	Intermediate Similarity	NPD5696	Approved
0.8163	Intermediate Similarity	NPD7521	Approved
0.8163	Intermediate Similarity	NPD6409	Approved
0.8163	Intermediate Similarity	NPD5330	Approved
0.8163	Intermediate Similarity	NPD7146	Approved
0.8163	Intermediate Similarity	NPD6684	Approved
0.8163	Intermediate Similarity	NPD7334	Approved
0.8155	Intermediate Similarity	NPD4697	Phase 3
0.8137	Intermediate Similarity	NPD7748	Approved
0.8136	Intermediate Similarity	NPD8293	Discontinued
0.812	Intermediate Similarity	NPD7492	Approved
0.8119	Intermediate Similarity	NPD6079	Approved
0.8095	Intermediate Similarity	NPD4700	Approved
0.8095	Intermediate Similarity	NPD4696	Approved
0.8095	Intermediate Similarity	NPD5285	Approved
0.8095	Intermediate Similarity	NPD5286	Approved
0.8087	Intermediate Similarity	NPD6059	Approved
0.8087	Intermediate Similarity	NPD6054	Approved
0.8067	Intermediate Similarity	NPD7736	Approved
0.8058	Intermediate Similarity	NPD5695	Phase 3
0.8051	Intermediate Similarity	NPD6616	Approved
0.8	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD7078	Approved
0.798	Intermediate Similarity	NPD3618	Phase 1
0.7961	Intermediate Similarity	NPD7900	Approved
0.7961	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6001	Approved
0.7949	Intermediate Similarity	NPD6370	Approved
0.7944	Intermediate Similarity	NPD5226	Approved
0.7944	Intermediate Similarity	NPD5211	Phase 2
0.7944	Intermediate Similarity	NPD4633	Approved
0.7944	Intermediate Similarity	NPD5224	Approved
0.7944	Intermediate Similarity	NPD5225	Approved
0.7941	Intermediate Similarity	NPD8034	Phase 2
0.7941	Intermediate Similarity	NPD8035	Phase 2
0.7931	Intermediate Similarity	NPD6319	Approved
0.7895	Intermediate Similarity	NPD6274	Approved
0.787	Intermediate Similarity	NPD5174	Approved
0.787	Intermediate Similarity	NPD5175	Approved
0.7864	Intermediate Similarity	NPD4202	Approved
0.7863	Intermediate Similarity	NPD6015	Approved
0.7863	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD6016	Approved
0.785	Intermediate Similarity	NPD5223	Approved
0.7845	Intermediate Similarity	NPD7100	Approved
0.7845	Intermediate Similarity	NPD7101	Approved
0.7826	Intermediate Similarity	NPD7115	Discovery
0.7822	Intermediate Similarity	NPD6672	Approved
0.7822	Intermediate Similarity	NPD5737	Approved
0.781	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD5221	Approved
0.781	Intermediate Similarity	NPD5222	Approved
0.78	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD5141	Approved
0.7797	Intermediate Similarity	NPD5988	Approved
0.7778	Intermediate Similarity	NPD3665	Phase 1
0.7778	Intermediate Similarity	NPD3133	Approved
0.7778	Intermediate Similarity	NPD3666	Approved
0.7768	Intermediate Similarity	NPD4634	Approved
0.7767	Intermediate Similarity	NPD7515	Phase 2
0.7759	Intermediate Similarity	NPD6335	Approved
0.7745	Intermediate Similarity	NPD4753	Phase 2
0.7745	Intermediate Similarity	NPD6673	Approved
0.7745	Intermediate Similarity	NPD6080	Approved
0.7745	Intermediate Similarity	NPD6904	Approved
0.7736	Intermediate Similarity	NPD5173	Approved
0.7727	Intermediate Similarity	NPD4768	Approved
0.7727	Intermediate Similarity	NPD4767	Approved
0.7719	Intermediate Similarity	NPD4632	Approved
0.7712	Intermediate Similarity	NPD6909	Approved
0.7712	Intermediate Similarity	NPD6908	Approved
0.7706	Intermediate Similarity	NPD4754	Approved
0.7672	Intermediate Similarity	NPD6317	Approved
0.767	Intermediate Similarity	NPD5207	Approved
0.7664	Intermediate Similarity	NPD7638	Approved
0.7607	Intermediate Similarity	NPD6313	Approved
0.7607	Intermediate Similarity	NPD6314	Approved
0.76	Intermediate Similarity	NPD4786	Approved
0.7596	Intermediate Similarity	NPD5284	Approved
0.7596	Intermediate Similarity	NPD5281	Approved
0.7593	Intermediate Similarity	NPD7639	Approved
0.7593	Intermediate Similarity	NPD7640	Approved
0.7589	Intermediate Similarity	NPD4730	Approved
0.7589	Intermediate Similarity	NPD4729	Approved
0.7589	Intermediate Similarity	NPD5128	Approved
0.7586	Intermediate Similarity	NPD6868	Approved
0.7576	Intermediate Similarity	NPD4221	Approved
0.7576	Intermediate Similarity	NPD4223	Phase 3
0.7547	Intermediate Similarity	NPD4629	Approved
0.7547	Intermediate Similarity	NPD5210	Approved
0.7525	Intermediate Similarity	NPD5329	Approved
0.7521	Intermediate Similarity	NPD6009	Approved
0.748	Intermediate Similarity	NPD6033	Approved
0.7476	Intermediate Similarity	NPD5208	Approved
0.7456	Intermediate Similarity	NPD5251	Approved
0.7456	Intermediate Similarity	NPD5250	Approved
0.7456	Intermediate Similarity	NPD5249	Phase 3
0.7456	Intermediate Similarity	NPD5247	Approved
0.7456	Intermediate Similarity	NPD5248	Approved
0.7451	Intermediate Similarity	NPD6098	Approved
0.7438	Intermediate Similarity	NPD7604	Phase 2
0.7429	Intermediate Similarity	NPD6050	Approved
0.7429	Intermediate Similarity	NPD5693	Phase 1
0.7429	Intermediate Similarity	NPD6411	Approved
0.7426	Intermediate Similarity	NPD4197	Approved
0.7419	Intermediate Similarity	NPD7319	Approved
0.7417	Intermediate Similarity	NPD5983	Phase 2
0.74	Intermediate Similarity	NPD3667	Approved
0.7391	Intermediate Similarity	NPD5215	Approved
0.7391	Intermediate Similarity	NPD5217	Approved
0.7391	Intermediate Similarity	NPD5216	Approved
0.7387	Intermediate Similarity	NPD6052	Approved
0.7379	Intermediate Similarity	NPD3573	Approved
0.7353	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6412	Phase 2
0.7339	Intermediate Similarity	NPD4225	Approved
0.7333	Intermediate Similarity	NPD5692	Phase 3
0.7317	Intermediate Similarity	NPD7507	Approved
0.7317	Intermediate Similarity	NPD6336	Discontinued
0.7304	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5169	Approved
0.7304	Intermediate Similarity	NPD5135	Approved
0.7295	Intermediate Similarity	NPD8328	Phase 3
0.7282	Intermediate Similarity	NPD4689	Approved
0.7282	Intermediate Similarity	NPD4690	Approved
0.7282	Intermediate Similarity	NPD4138	Approved
0.7282	Intermediate Similarity	NPD4688	Approved
0.7282	Intermediate Similarity	NPD4693	Phase 3
0.7282	Intermediate Similarity	NPD5205	Approved
0.7264	Intermediate Similarity	NPD5694	Approved
0.7241	Intermediate Similarity	NPD5127	Approved
0.7238	Intermediate Similarity	NPD6101	Approved
0.7238	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6053	Discontinued
0.713	Intermediate Similarity	NPD5168	Approved
0.7115	Intermediate Similarity	NPD5279	Phase 3
0.7115	Intermediate Similarity	NPD4694	Approved
0.7115	Intermediate Similarity	NPD5280	Approved
0.7115	Intermediate Similarity	NPD5690	Phase 2
0.7115	Intermediate Similarity	NPD5786	Approved
0.7087	Intermediate Similarity	NPD3668	Phase 3
0.7064	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6435	Approved
0.7059	Intermediate Similarity	NPD5167	Approved
0.7019	Intermediate Similarity	NPD1694	Approved
0.7016	Intermediate Similarity	NPD6067	Discontinued
0.7009	Intermediate Similarity	NPD5785	Approved
0.6991	Remote Similarity	NPD7632	Discontinued
0.699	Remote Similarity	NPD4788	Approved
0.697	Remote Similarity	NPD6334	Approved
0.697	Remote Similarity	NPD6333	Approved
0.6961	Remote Similarity	NPD5369	Approved
0.6931	Remote Similarity	NPD4195	Approved
0.6923	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6051	Approved
0.6909	Remote Similarity	NPD5654	Approved
0.6897	Remote Similarity	NPD6614	Approved
0.6881	Remote Similarity	NPD5778	Approved
0.6881	Remote Similarity	NPD5779	Approved
0.6864	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7525	Registered
0.6863	Remote Similarity	NPD5368	Approved
0.6857	Remote Similarity	NPD5363	Approved
0.6838	Remote Similarity	NPD5345	Clinical (unspecified phase)

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