NPASS Compound

Structure

NPC476186 OpenBabel07101718312D 34 38 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 2.3230 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 2.8660 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 5.2574 -3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2793 -3.4190 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 3.2709 -0.5000 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 2.6831 0.3090 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5665 -4.5780 0.0000 C 0 0 0 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 2.6831 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9703 -2.4680 0.0000 C 0 0 3 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 0.8660 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 6.5446 -4.7859 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 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 4.6394 -1.7248 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 6.8536 -5.7370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2137 -4.0428 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 4 26 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 18 2 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 25 1 0 0 0 0 19 2 1 1 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 27 1 6 0 0 0 21 31 1 0 0 0 0 22 26 1 0 0 0 0 22 29 1 6 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 32 1 1 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 27 28 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	514.542
LogP:	5.268
LogD:	4.001
LogS:	-3.885
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.416
Synthetic Accessibility Score:	5.667
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.231
MDCK Permeability:	1.558701114845462e-05
Pgp-inhibitor:	0.397
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.062
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11
Plasma Protein Binding (PPB):	95.70880889892578%
Volume Distribution (VD):	0.75
Pgp-substrate:	2.758638620376587%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.363
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.713
CYP2C9-inhibitor:	0.171
CYP2C9-substrate:	0.602
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	0.43
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	2.641
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.587
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.578
Maximum Recommended Daily Dose:	0.762
Skin Sensitization:	0.945
Carcinogencity:	0.041
Eye Corrosion:	0.023
Eye Irritation:	0.152
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC476186

Natural Product ID:	NPC476186
*Common Name:**	WCKMOTWOWWZGCU-GXRZVIAZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WCKMOTWOWWZGCU-GXRZVIAZSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-18(25(33)34)7-8-21(31)19(2)20-11-13-28(6)23-10-9-22-26(3,4)24(32)12-14-29(22)17-30(23,29)16-15-27(20,28)5/h7,19-24,31-32H,8-17H2,1-6H3,(H,33,34)/b18-7+/t19-,20+,21?,22-,23-,24+,27+,28-,29+,30-/m0/s1
SMILES:	OC([C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@H](C2(C)C)O)C)C)C/C=C(/C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL551734
PubChem CID:	14314559
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
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757720]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593279]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	China	n.a.	PMID[19278239]
NPO32948	propolis	Genus	Rhytismataceae	Eukaryota	n.a.	Ywar Taw village, Shan State of Myanmar	2006-Dec	PMID[19572611]

☑ 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
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	CD100	=	25.0	uM	PMID[538593]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	13.4	uM	PMID[538593]

☑ 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 NPC476186 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	179
0.1-0.2	1195
0.2-0.3	4664
0.3-0.4	14051
0.4-0.5	8420
0.5-0.6	6303
0.6-0.7	5301
0.7-0.8	2397
0.8-0.85	146
0.85-0.9	26
0.9-0.95	4
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9885	High Similarity	NPC476304
0.977	High Similarity	NPC110923
0.977	High Similarity	NPC74296
0.9556	High Similarity	NPC114743
0.9556	High Similarity	NPC195366
0.9318	High Similarity	NPC262858
0.9318	High Similarity	NPC146554
0.9318	High Similarity	NPC472240
0.9121	High Similarity	NPC119562
0.9121	High Similarity	NPC279410
0.9022	High Similarity	NPC476174
0.9011	High Similarity	NPC214697
0.9011	High Similarity	NPC38232
0.8936	High Similarity	NPC218107
0.8901	High Similarity	NPC212948
0.8876	High Similarity	NPC89747
0.883	High Similarity	NPC141401
0.883	High Similarity	NPC99726
0.8763	High Similarity	NPC297617
0.8723	High Similarity	NPC54248
0.8723	High Similarity	NPC29152
0.8723	High Similarity	NPC276103
0.8652	High Similarity	NPC22133
0.8646	High Similarity	NPC470074
0.8632	High Similarity	NPC156546
0.8621	High Similarity	NPC159148
0.8571	High Similarity	NPC67872
0.8571	High Similarity	NPC476237
0.8556	High Similarity	NPC474970
0.8526	High Similarity	NPC250757
0.8526	High Similarity	NPC190713
0.8526	High Similarity	NPC301534
0.8523	High Similarity	NPC2524
0.8506	High Similarity	NPC281880
0.8478	Intermediate Similarity	NPC128496
0.8478	Intermediate Similarity	NPC314727
0.8454	Intermediate Similarity	NPC251680
0.8454	Intermediate Similarity	NPC201406
0.8438	Intermediate Similarity	NPC320306
0.8438	Intermediate Similarity	NPC253826
0.8438	Intermediate Similarity	NPC108078
0.8427	Intermediate Similarity	NPC79945
0.8427	Intermediate Similarity	NPC82623
0.8404	Intermediate Similarity	NPC12722
0.8387	Intermediate Similarity	NPC48010
0.8387	Intermediate Similarity	NPC78973
0.8384	Intermediate Similarity	NPC112009
0.837	Intermediate Similarity	NPC104560
0.837	Intermediate Similarity	NPC117122
0.8367	Intermediate Similarity	NPC118174
0.8352	Intermediate Similarity	NPC186975
0.8352	Intermediate Similarity	NPC475069
0.8352	Intermediate Similarity	NPC175145
0.8351	Intermediate Similarity	NPC98868
0.8333	Intermediate Similarity	NPC472941
0.8333	Intermediate Similarity	NPC33913
0.8333	Intermediate Similarity	NPC456
0.8333	Intermediate Similarity	NPC472265
0.8316	Intermediate Similarity	NPC474922
0.8316	Intermediate Similarity	NPC469406
0.8316	Intermediate Similarity	NPC201725
0.8315	Intermediate Similarity	NPC101462
0.8315	Intermediate Similarity	NPC296701
0.8315	Intermediate Similarity	NPC218616
0.8298	Intermediate Similarity	NPC473998
0.8298	Intermediate Similarity	NPC470113
0.8298	Intermediate Similarity	NPC329842
0.8298	Intermediate Similarity	NPC476187
0.8283	Intermediate Similarity	NPC136289
0.8283	Intermediate Similarity	NPC293753
0.828	Intermediate Similarity	NPC475921
0.828	Intermediate Similarity	NPC309603
0.828	Intermediate Similarity	NPC66344
0.828	Intermediate Similarity	NPC474704
0.828	Intermediate Similarity	NPC473999
0.8276	Intermediate Similarity	NPC85346
0.8276	Intermediate Similarity	NPC65897
0.8276	Intermediate Similarity	NPC302041
0.8265	Intermediate Similarity	NPC327431
0.8265	Intermediate Similarity	NPC266955
0.8265	Intermediate Similarity	NPC476303
0.8261	Intermediate Similarity	NPC474684
0.8261	Intermediate Similarity	NPC236618
0.8261	Intermediate Similarity	NPC142361
0.8242	Intermediate Similarity	NPC109528
0.8229	Intermediate Similarity	NPC84383
0.8229	Intermediate Similarity	NPC318282
0.8229	Intermediate Similarity	NPC174948
0.8229	Intermediate Similarity	NPC469995
0.8229	Intermediate Similarity	NPC173875
0.8222	Intermediate Similarity	NPC139206
0.8222	Intermediate Similarity	NPC476927
0.8222	Intermediate Similarity	NPC134481
0.8202	Intermediate Similarity	NPC170303
0.82	Intermediate Similarity	NPC171014
0.82	Intermediate Similarity	NPC312900
0.82	Intermediate Similarity	NPC180204
0.82	Intermediate Similarity	NPC85742
0.82	Intermediate Similarity	NPC176883
0.8191	Intermediate Similarity	NPC126993
0.8191	Intermediate Similarity	NPC469400
0.8182	Intermediate Similarity	NPC143182
0.8182	Intermediate Similarity	NPC115899
0.8182	Intermediate Similarity	NPC247701
0.8182	Intermediate Similarity	NPC28862
0.8182	Intermediate Similarity	NPC25177
0.8182	Intermediate Similarity	NPC47982
0.8182	Intermediate Similarity	NPC30986
0.8182	Intermediate Similarity	NPC295110
0.8182	Intermediate Similarity	NPC81306
0.8182	Intermediate Similarity	NPC268829
0.8182	Intermediate Similarity	NPC81530
0.8182	Intermediate Similarity	NPC282524
0.8182	Intermediate Similarity	NPC109546
0.8182	Intermediate Similarity	NPC84694
0.8182	Intermediate Similarity	NPC209430
0.8182	Intermediate Similarity	NPC222875
0.8173	Intermediate Similarity	NPC470076
0.8172	Intermediate Similarity	NPC16377
0.8172	Intermediate Similarity	NPC242864
0.8163	Intermediate Similarity	NPC114274
0.8163	Intermediate Similarity	NPC235464
0.8163	Intermediate Similarity	NPC478056
0.8163	Intermediate Similarity	NPC197386
0.8163	Intermediate Similarity	NPC108368
0.8163	Intermediate Similarity	NPC194196
0.8163	Intermediate Similarity	NPC92275
0.8163	Intermediate Similarity	NPC166745
0.8163	Intermediate Similarity	NPC57079
0.8161	Intermediate Similarity	NPC331618
0.8161	Intermediate Similarity	NPC257191
0.8152	Intermediate Similarity	NPC155011
0.8152	Intermediate Similarity	NPC6391
0.8152	Intermediate Similarity	NPC261266
0.8152	Intermediate Similarity	NPC168231
0.8152	Intermediate Similarity	NPC70661
0.8144	Intermediate Similarity	NPC327788
0.8144	Intermediate Similarity	NPC235053
0.8144	Intermediate Similarity	NPC328371
0.8137	Intermediate Similarity	NPC79298
0.8137	Intermediate Similarity	NPC43063
0.8137	Intermediate Similarity	NPC472925
0.8132	Intermediate Similarity	NPC205845
0.8132	Intermediate Similarity	NPC306951
0.8132	Intermediate Similarity	NPC302360
0.8132	Intermediate Similarity	NPC185568
0.8132	Intermediate Similarity	NPC194937
0.8132	Intermediate Similarity	NPC476038
0.8125	Intermediate Similarity	NPC8993
0.8125	Intermediate Similarity	NPC474690
0.8125	Intermediate Similarity	NPC299100
0.8125	Intermediate Similarity	NPC166906
0.8125	Intermediate Similarity	NPC57117
0.8119	Intermediate Similarity	NPC72255
0.8119	Intermediate Similarity	NPC201763
0.8111	Intermediate Similarity	NPC256112
0.8111	Intermediate Similarity	NPC49964
0.8105	Intermediate Similarity	NPC177641
0.8105	Intermediate Similarity	NPC272746
0.8105	Intermediate Similarity	NPC72845
0.8105	Intermediate Similarity	NPC23217
0.8105	Intermediate Similarity	NPC234335
0.8105	Intermediate Similarity	NPC475806
0.8105	Intermediate Similarity	NPC189520
0.81	Intermediate Similarity	NPC234892
0.809	Intermediate Similarity	NPC236237
0.809	Intermediate Similarity	NPC234193
0.809	Intermediate Similarity	NPC102253
0.809	Intermediate Similarity	NPC322313
0.8085	Intermediate Similarity	NPC50488
0.8085	Intermediate Similarity	NPC31985
0.8085	Intermediate Similarity	NPC177141
0.8085	Intermediate Similarity	NPC1015
0.8085	Intermediate Similarity	NPC474396
0.8085	Intermediate Similarity	NPC214387
0.8081	Intermediate Similarity	NPC471041
0.8081	Intermediate Similarity	NPC287833
0.8081	Intermediate Similarity	NPC476274
0.8068	Intermediate Similarity	NPC285761
0.8068	Intermediate Similarity	NPC6978
0.8068	Intermediate Similarity	NPC244385
0.8068	Intermediate Similarity	NPC312328
0.8068	Intermediate Similarity	NPC472342
0.8068	Intermediate Similarity	NPC167037
0.8068	Intermediate Similarity	NPC138621
0.8068	Intermediate Similarity	NPC474216
0.8065	Intermediate Similarity	NPC159046
0.8065	Intermediate Similarity	NPC233836
0.8065	Intermediate Similarity	NPC187376
0.8065	Intermediate Similarity	NPC475740
0.8065	Intermediate Similarity	NPC475772
0.8061	Intermediate Similarity	NPC231751
0.8058	Intermediate Similarity	NPC275060
0.8058	Intermediate Similarity	NPC295244
0.8046	Intermediate Similarity	NPC237460
0.8043	Intermediate Similarity	NPC266511
0.8043	Intermediate Similarity	NPC283733
0.8043	Intermediate Similarity	NPC60350
0.8043	Intermediate Similarity	NPC76518
0.8043	Intermediate Similarity	NPC474013

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 NPC476186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1398
0.2-0.3	4006
0.3-0.4	2535
0.4-0.5	594
0.5-0.6	179
0.6-0.7	202
0.7-0.8	86
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8454	Intermediate Similarity	NPD7640	Approved
0.8454	Intermediate Similarity	NPD7639	Approved
0.8351	Intermediate Similarity	NPD7638	Approved
0.809	Intermediate Similarity	NPD7525	Registered
0.7917	Intermediate Similarity	NPD7515	Phase 2
0.7917	Intermediate Similarity	NPD6079	Approved
0.7895	Intermediate Similarity	NPD5328	Approved
0.7849	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD4225	Approved
0.7798	Intermediate Similarity	NPD7115	Discovery
0.7766	Intermediate Similarity	NPD3618	Phase 1
0.7745	Intermediate Similarity	NPD7632	Discontinued
0.7742	Intermediate Similarity	NPD4786	Approved
0.7727	Intermediate Similarity	NPD6942	Approved
0.7727	Intermediate Similarity	NPD7339	Approved
0.7653	Intermediate Similarity	NPD6399	Phase 3
0.76	Intermediate Similarity	NPD5222	Approved
0.76	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5221	Approved
0.7576	Intermediate Similarity	NPD7748	Approved
0.7573	Intermediate Similarity	NPD5211	Phase 2
0.7547	Intermediate Similarity	NPD6899	Approved
0.7547	Intermediate Similarity	NPD6881	Approved
0.7527	Intermediate Similarity	NPD3667	Approved
0.7525	Intermediate Similarity	NPD5173	Approved
0.7524	Intermediate Similarity	NPD7128	Approved
0.7524	Intermediate Similarity	NPD6402	Approved
0.7524	Intermediate Similarity	NPD5739	Approved
0.7524	Intermediate Similarity	NPD6675	Approved
0.7475	Intermediate Similarity	NPD4202	Approved
0.7453	Intermediate Similarity	NPD5697	Approved
0.7444	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5141	Approved
0.7426	Intermediate Similarity	NPD4697	Phase 3
0.7407	Intermediate Similarity	NPD7290	Approved
0.7407	Intermediate Similarity	NPD6883	Approved
0.7407	Intermediate Similarity	NPD7102	Approved
0.7383	Intermediate Similarity	NPD6011	Approved
0.7383	Intermediate Similarity	NPD7320	Approved
0.7379	Intermediate Similarity	NPD5286	Approved
0.7379	Intermediate Similarity	NPD4696	Approved
0.7379	Intermediate Similarity	NPD5285	Approved
0.7374	Intermediate Similarity	NPD8035	Phase 2
0.7374	Intermediate Similarity	NPD7637	Suspended
0.7374	Intermediate Similarity	NPD8034	Phase 2
0.7368	Intermediate Similarity	NPD3665	Phase 1
0.7368	Intermediate Similarity	NPD3666	Approved
0.7368	Intermediate Similarity	NPD3133	Approved
0.7353	Intermediate Similarity	NPD6083	Phase 2
0.7353	Intermediate Similarity	NPD4755	Approved
0.7353	Intermediate Similarity	NPD6084	Phase 2
0.7353	Intermediate Similarity	NPD7902	Approved
0.7339	Intermediate Similarity	NPD6869	Approved
0.7339	Intermediate Similarity	NPD8130	Phase 1
0.7339	Intermediate Similarity	NPD6617	Approved
0.7339	Intermediate Similarity	NPD6649	Approved
0.7339	Intermediate Similarity	NPD6847	Approved
0.7339	Intermediate Similarity	NPD6650	Approved
0.7327	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6012	Approved
0.7315	Intermediate Similarity	NPD6372	Approved
0.7315	Intermediate Similarity	NPD6014	Approved
0.7315	Intermediate Similarity	NPD6373	Approved
0.7315	Intermediate Similarity	NPD6013	Approved
0.7308	Intermediate Similarity	NPD5223	Approved
0.729	Intermediate Similarity	NPD5701	Approved
0.7273	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD8297	Approved
0.7253	Intermediate Similarity	NPD6117	Approved
0.7245	Intermediate Similarity	NPD6672	Approved
0.7245	Intermediate Similarity	NPD5737	Approved
0.7245	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4633	Approved
0.7238	Intermediate Similarity	NPD5226	Approved
0.7238	Intermediate Similarity	NPD5225	Approved
0.7238	Intermediate Similarity	NPD5224	Approved
0.7234	Intermediate Similarity	NPD6902	Approved
0.7222	Intermediate Similarity	NPD6926	Approved
0.7222	Intermediate Similarity	NPD6924	Approved
0.7216	Intermediate Similarity	NPD6409	Approved
0.7216	Intermediate Similarity	NPD6684	Approved
0.7216	Intermediate Similarity	NPD7146	Approved
0.7216	Intermediate Similarity	NPD5330	Approved
0.7216	Intermediate Similarity	NPD7521	Approved
0.7216	Intermediate Similarity	NPD7334	Approved
0.7212	Intermediate Similarity	NPD4700	Approved
0.7204	Intermediate Similarity	NPD6929	Approved
0.7204	Intermediate Similarity	NPD4195	Approved
0.7204	Intermediate Similarity	NPD7645	Phase 2
0.7182	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6116	Phase 1
0.7172	Intermediate Similarity	NPD6051	Approved
0.7172	Intermediate Similarity	NPD4753	Phase 2
0.717	Intermediate Similarity	NPD5174	Approved
0.717	Intermediate Similarity	NPD5175	Approved
0.7128	Intermediate Similarity	NPD6930	Phase 2
0.7128	Intermediate Similarity	NPD6931	Approved
0.7105	Intermediate Similarity	NPD7328	Approved
0.7105	Intermediate Similarity	NPD7327	Approved
0.7097	Intermediate Similarity	NPD6115	Approved
0.7097	Intermediate Similarity	NPD6118	Approved
0.7097	Intermediate Similarity	NPD6114	Approved
0.7097	Intermediate Similarity	NPD6697	Approved
0.7097	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6695	Phase 3
0.7083	Intermediate Similarity	NPD4788	Approved
0.708	Intermediate Similarity	NPD6868	Approved
0.7071	Intermediate Similarity	NPD6903	Approved
0.7069	Intermediate Similarity	NPD8033	Approved
0.7065	Intermediate Similarity	NPD6933	Approved
0.7059	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7900	Approved
0.7054	Intermediate Similarity	NPD4632	Approved
0.7043	Intermediate Similarity	NPD7516	Approved
0.7041	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5279	Phase 3
0.7037	Intermediate Similarity	NPD6008	Approved
0.7033	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD3668	Phase 3
0.7009	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD7152	Approved
0.7	Intermediate Similarity	NPD7150	Approved
0.7	Intermediate Similarity	NPD7151	Approved
0.699	Remote Similarity	NPD5695	Phase 3
0.699	Remote Similarity	NPD4629	Approved
0.699	Remote Similarity	NPD5210	Approved
0.6989	Remote Similarity	NPD6925	Approved
0.6989	Remote Similarity	NPD5776	Phase 2
0.6983	Remote Similarity	NPD8377	Approved
0.6983	Remote Similarity	NPD8294	Approved
0.6979	Remote Similarity	NPD4221	Approved
0.6979	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4223	Phase 3
0.6966	Remote Similarity	NPD6923	Approved
0.6966	Remote Similarity	NPD6922	Approved
0.6957	Remote Similarity	NPD6335	Approved
0.6952	Remote Similarity	NPD5290	Discontinued
0.6952	Remote Similarity	NPD5696	Approved
0.6949	Remote Similarity	NPD7604	Phase 2
0.6947	Remote Similarity	NPD7514	Phase 3
0.6939	Remote Similarity	NPD1696	Phase 3
0.6939	Remote Similarity	NPD5329	Approved
0.6939	Remote Similarity	NPD5363	Approved
0.6931	Remote Similarity	NPD5785	Approved
0.693	Remote Similarity	NPD6274	Approved
0.6923	Remote Similarity	NPD8379	Approved
0.6923	Remote Similarity	NPD8296	Approved
0.6923	Remote Similarity	NPD8378	Approved
0.6923	Remote Similarity	NPD8335	Approved
0.6923	Remote Similarity	NPD8380	Approved
0.6915	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7145	Approved
0.6909	Remote Similarity	NPD4729	Approved
0.6909	Remote Similarity	NPD4730	Approved
0.6909	Remote Similarity	NPD5128	Approved
0.6909	Remote Similarity	NPD5168	Approved
0.6907	Remote Similarity	NPD5331	Approved
0.6907	Remote Similarity	NPD5362	Discontinued
0.6907	Remote Similarity	NPD5332	Approved
0.6897	Remote Similarity	NPD7100	Approved
0.6897	Remote Similarity	NPD7101	Approved
0.6893	Remote Similarity	NPD6001	Approved
0.6889	Remote Similarity	NPD7144	Approved
0.6889	Remote Similarity	NPD7143	Approved
0.6887	Remote Similarity	NPD6404	Discontinued
0.6881	Remote Similarity	NPD4768	Approved
0.6881	Remote Similarity	NPD4767	Approved
0.6875	Remote Similarity	NPD4790	Discontinued
0.687	Remote Similarity	NPD6009	Approved
0.687	Remote Similarity	NPD6317	Approved
0.6863	Remote Similarity	NPD5281	Approved
0.6863	Remote Similarity	NPD5284	Approved
0.6848	Remote Similarity	NPD4785	Approved
0.6848	Remote Similarity	NPD4784	Approved
0.6837	Remote Similarity	NPD4197	Approved
0.6833	Remote Similarity	NPD7507	Approved
0.6832	Remote Similarity	NPD6673	Approved
0.6832	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6080	Approved
0.6832	Remote Similarity	NPD6904	Approved
0.6822	Remote Similarity	NPD5344	Discontinued
0.6813	Remote Similarity	NPD4243	Approved
0.681	Remote Similarity	NPD6313	Approved
0.681	Remote Similarity	NPD6314	Approved
0.68	Remote Similarity	NPD7750	Discontinued
0.68	Remote Similarity	NPD7524	Approved
0.6786	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5251	Approved
0.6786	Remote Similarity	NPD5247	Approved
0.6786	Remote Similarity	NPD5169	Approved
0.6786	Remote Similarity	NPD5248	Approved
0.6786	Remote Similarity	NPD5250	Approved
0.6786	Remote Similarity	NPD4634	Approved
0.6786	Remote Similarity	NPD5135	Approved
0.6786	Remote Similarity	NPD5249	Phase 3
0.678	Remote Similarity	NPD7503	Approved
0.6774	Remote Similarity	NPD8264	Approved
0.6771	Remote Similarity	NPD4819	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