NPASS Compound

Structure

NPC472227 OpenBabel07101718252D 34 39 0 0 1 0 0 0 0 0999 V2000 -2.4754 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4504 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7446 -4.3720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7196 -4.3720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3877 -1.0901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2511 -2.4683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2511 0.2881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6989 -3.0401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5433 -3.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5433 -0.6026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0764 -2.0651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2321 -1.5776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6989 -0.1151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9273 -1.8789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3542 -1.0901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9273 0.6737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9273 1.2763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5004 1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5004 0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5433 -1.5776 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6989 -2.0651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3877 -3.0401 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0764 -3.0401 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9273 2.2513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2321 -3.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3877 -2.0651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8546 -1.5776 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8546 -0.6026 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9273 -0.3013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9208 -3.5276 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2286 3.1786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 9 1 0 0 0 0 8 21 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 17 29 1 0 0 0 0 18 1 1 1 0 0 0 18 24 1 0 0 0 0 19 30 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 1 0 0 0 21 27 1 0 0 0 0 22 25 1 0 0 0 0 22 26 1 6 0 0 0 23 25 1 0 0 0 0 23 31 1 1 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 26 5 1 6 0 0 0 27 28 1 1 0 0 0 28 30 1 1 0 0 0 29 16 1 6 0 0 0 29 33 1 0 0 0 0 29 34 1 0 0 0 0 30 15 1 1 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	505.985
LogP:	5.2
LogD:	4.778
LogS:	-5.403
# Rotatable Bonds:	0
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.37
Synthetic Accessibility Score:	5.908
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.053
MDCK Permeability:	3.274739719927311e-05
Pgp-inhibitor:	0.866
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.374
30% Bioavailability (F30%):	0.791

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.311
Plasma Protein Binding (PPB):	91.79790496826172%
Volume Distribution (VD):	1.201
Pgp-substrate:	2.1751937866210938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.832
CYP2C19-inhibitor:	0.304
CYP2C19-substrate:	0.951
CYP2C9-inhibitor:	0.422
CYP2C9-substrate:	0.204
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	11.843
Half-life (T1/2):	0.273

ADMET: Toxicity

hERG Blockers:	0.214
Human Hepatotoxicity (H-HT):	0.451
Drug-inuced Liver Injury (DILI):	0.37
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.91
Carcinogencity:	0.142
Eye Corrosion:	0.018
Eye Irritation:	0.116
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC472227

Natural Product ID:	NPC472227
*Common Name:**	XWDMDRKNNBPHJI-AYLXSBHYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XWDMDRKNNBPHJI-AYLXSBHYSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-18-16-29(33-24(18)32)17-19(2)30(34-29)15-14-27(6)21-8-9-22-25(3,4)23(31)11-12-26(22,5)20(21)10-13-28(27,30)7/h8,18-20,22-23,31H,9-17H2,1-7H3/t18-,19-,20-,22+,23-,26-,27+,28+,29-,30-/m1/s1
SMILES:	O=C1O[C@@]2(C[C@H]1C)C[C@H]([C@]1(O2)CC[C@@]2([C@]1(C)CC[C@@H]1C2=CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3353844
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO33399	abies faxoniana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25554367]

☑ 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	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[510928]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	19100.0	nM	PMID[510928]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16400.0	nM	PMID[510928]
NPT27	Others	Unspecified		IC50	=	17600.0	nM	PMID[510928]

☑ 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 NPC472227 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	214
0.1-0.2	1403
0.2-0.3	5489
0.3-0.4	14895
0.4-0.5	6944
0.5-0.6	5760
0.6-0.7	6203
0.7-0.8	1710
0.8-0.85	71
0.85-0.9	6
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472228
0.8958	High Similarity	NPC470375
0.8958	High Similarity	NPC470224
0.8958	High Similarity	NPC470376
0.8866	High Similarity	NPC472223
0.8866	High Similarity	NPC472224
0.8776	High Similarity	NPC69548
0.8776	High Similarity	NPC184848
0.8725	High Similarity	NPC140723
0.87	High Similarity	NPC477813
0.866	High Similarity	NPC154101
0.866	High Similarity	NPC23434
0.86	High Similarity	NPC475894
0.8586	High Similarity	NPC222845
0.8586	High Similarity	NPC45324
0.8586	High Similarity	NPC469599
0.8586	High Similarity	NPC162001
0.8585	High Similarity	NPC101450
0.8557	High Similarity	NPC471896
0.8515	High Similarity	NPC186810
0.8469	Intermediate Similarity	NPC150383
0.8462	Intermediate Similarity	NPC471293
0.8454	Intermediate Similarity	NPC475921
0.8454	Intermediate Similarity	NPC474704
0.8447	Intermediate Similarity	NPC22388
0.8438	Intermediate Similarity	NPC142361
0.8438	Intermediate Similarity	NPC474684
0.8438	Intermediate Similarity	NPC167877
0.8416	Intermediate Similarity	NPC107243
0.8416	Intermediate Similarity	NPC57416
0.84	Intermediate Similarity	NPC279974
0.8396	Intermediate Similarity	NPC258323
0.8384	Intermediate Similarity	NPC170220
0.8384	Intermediate Similarity	NPC141497
0.8384	Intermediate Similarity	NPC472232
0.8384	Intermediate Similarity	NPC472231
0.8384	Intermediate Similarity	NPC107674
0.8367	Intermediate Similarity	NPC148414
0.8367	Intermediate Similarity	NPC175628
0.8367	Intermediate Similarity	NPC111585
0.8365	Intermediate Similarity	NPC36688
0.8351	Intermediate Similarity	NPC294480
0.8351	Intermediate Similarity	NPC28227
0.8349	Intermediate Similarity	NPC178981
0.8333	Intermediate Similarity	NPC48647
0.8333	Intermediate Similarity	NPC73038
0.8333	Intermediate Similarity	NPC477854
0.8317	Intermediate Similarity	NPC322063
0.8302	Intermediate Similarity	NPC220974
0.8302	Intermediate Similarity	NPC59530
0.83	Intermediate Similarity	NPC159410
0.8283	Intermediate Similarity	NPC110657
0.8283	Intermediate Similarity	NPC26888
0.8283	Intermediate Similarity	NPC212301
0.8283	Intermediate Similarity	NPC189520
0.8283	Intermediate Similarity	NPC86266
0.8283	Intermediate Similarity	NPC297265
0.8265	Intermediate Similarity	NPC474889
0.8265	Intermediate Similarity	NPC476733
0.8265	Intermediate Similarity	NPC215029
0.8265	Intermediate Similarity	NPC54689
0.8252	Intermediate Similarity	NPC108371
0.8247	Intermediate Similarity	NPC159046
0.8247	Intermediate Similarity	NPC233836
0.8247	Intermediate Similarity	NPC187376
0.8247	Intermediate Similarity	NPC312215
0.8241	Intermediate Similarity	NPC163314
0.8224	Intermediate Similarity	NPC469844
0.8208	Intermediate Similarity	NPC231530
0.8208	Intermediate Similarity	NPC278628
0.8205	Intermediate Similarity	NPC473888
0.82	Intermediate Similarity	NPC474436
0.82	Intermediate Similarity	NPC66429
0.82	Intermediate Similarity	NPC49776
0.82	Intermediate Similarity	NPC472225
0.82	Intermediate Similarity	NPC243866
0.82	Intermediate Similarity	NPC63118
0.82	Intermediate Similarity	NPC152897
0.82	Intermediate Similarity	NPC472226
0.8198	Intermediate Similarity	NPC266728
0.8198	Intermediate Similarity	NPC49492
0.8182	Intermediate Similarity	NPC171441
0.8182	Intermediate Similarity	NPC52634
0.8182	Intermediate Similarity	NPC469400
0.8182	Intermediate Similarity	NPC44240
0.8173	Intermediate Similarity	NPC474327
0.8163	Intermediate Similarity	NPC242864
0.8163	Intermediate Similarity	NPC183546
0.8155	Intermediate Similarity	NPC309493
0.8155	Intermediate Similarity	NPC164349
0.8155	Intermediate Similarity	NPC119036
0.8144	Intermediate Similarity	NPC325594
0.8144	Intermediate Similarity	NPC6979
0.8144	Intermediate Similarity	NPC474970
0.8144	Intermediate Similarity	NPC28252
0.8144	Intermediate Similarity	NPC212843
0.8144	Intermediate Similarity	NPC55309
0.8144	Intermediate Similarity	NPC155011
0.8137	Intermediate Similarity	NPC477853
0.8137	Intermediate Similarity	NPC155676
0.8137	Intermediate Similarity	NPC173272
0.8137	Intermediate Similarity	NPC327179
0.8131	Intermediate Similarity	NPC44063
0.8131	Intermediate Similarity	NPC131665
0.8131	Intermediate Similarity	NPC255387
0.8125	Intermediate Similarity	NPC100391
0.8119	Intermediate Similarity	NPC471720
0.8119	Intermediate Similarity	NPC49670
0.8119	Intermediate Similarity	NPC111015
0.8113	Intermediate Similarity	NPC31430
0.8113	Intermediate Similarity	NPC100955
0.8113	Intermediate Similarity	NPC121566
0.8113	Intermediate Similarity	NPC85593
0.8113	Intermediate Similarity	NPC29705
0.8108	Intermediate Similarity	NPC471398
0.8095	Intermediate Similarity	NPC136289
0.8095	Intermediate Similarity	NPC473928
0.8081	Intermediate Similarity	NPC84271
0.8081	Intermediate Similarity	NPC102414
0.8081	Intermediate Similarity	NPC155479
0.8081	Intermediate Similarity	NPC77168
0.8081	Intermediate Similarity	NPC474679
0.8077	Intermediate Similarity	NPC218383
0.8077	Intermediate Similarity	NPC476303
0.8077	Intermediate Similarity	NPC154072
0.8073	Intermediate Similarity	NPC98633
0.807	Intermediate Similarity	NPC471406
0.8058	Intermediate Similarity	NPC253586
0.8056	Intermediate Similarity	NPC94529
0.8041	Intermediate Similarity	NPC470223
0.8041	Intermediate Similarity	NPC474218
0.8039	Intermediate Similarity	NPC205173
0.8039	Intermediate Similarity	NPC472485
0.8039	Intermediate Similarity	NPC263347
0.8039	Intermediate Similarity	NPC48330
0.8037	Intermediate Similarity	NPC95243
0.8037	Intermediate Similarity	NPC196528
0.8037	Intermediate Similarity	NPC470309
0.8037	Intermediate Similarity	NPC63023
0.802	Intermediate Similarity	NPC118519
0.802	Intermediate Similarity	NPC158059
0.802	Intermediate Similarity	NPC277721
0.802	Intermediate Similarity	NPC202728
0.802	Intermediate Similarity	NPC267266
0.802	Intermediate Similarity	NPC470656
0.8019	Intermediate Similarity	NPC476237
0.8019	Intermediate Similarity	NPC36321
0.8019	Intermediate Similarity	NPC112009
0.8018	Intermediate Similarity	NPC285086
0.8018	Intermediate Similarity	NPC250109
0.8018	Intermediate Similarity	NPC962
0.8	Intermediate Similarity	NPC210037
0.8	Intermediate Similarity	NPC474022
0.8	Intermediate Similarity	NPC273621
0.8	Intermediate Similarity	NPC227467
0.8	Intermediate Similarity	NPC81530
0.8	Intermediate Similarity	NPC250481
0.8	Intermediate Similarity	NPC263827
0.8	Intermediate Similarity	NPC477053
0.8	Intermediate Similarity	NPC18872
0.8	Intermediate Similarity	NPC120968
0.8	Intermediate Similarity	NPC477872
0.8	Intermediate Similarity	NPC46281
0.8	Intermediate Similarity	NPC477051
0.8	Intermediate Similarity	NPC477052
0.8	Intermediate Similarity	NPC43775
0.8	Intermediate Similarity	NPC285410
0.8	Intermediate Similarity	NPC7260
0.8	Intermediate Similarity	NPC123854
0.8	Intermediate Similarity	NPC290614
0.7982	Intermediate Similarity	NPC265655
0.7982	Intermediate Similarity	NPC477071
0.7982	Intermediate Similarity	NPC2766
0.7981	Intermediate Similarity	NPC271387
0.7981	Intermediate Similarity	NPC153792
0.7981	Intermediate Similarity	NPC473155
0.798	Intermediate Similarity	NPC48866
0.798	Intermediate Similarity	NPC247406
0.7963	Intermediate Similarity	NPC293512
0.7963	Intermediate Similarity	NPC64844
0.7963	Intermediate Similarity	NPC42847
0.7961	Intermediate Similarity	NPC253115
0.7961	Intermediate Similarity	NPC120708
0.7961	Intermediate Similarity	NPC327788
0.7961	Intermediate Similarity	NPC304899
0.7961	Intermediate Similarity	NPC235053
0.7946	Intermediate Similarity	NPC123117
0.7946	Intermediate Similarity	NPC477580
0.7944	Intermediate Similarity	NPC477812
0.7941	Intermediate Similarity	NPC469406
0.7941	Intermediate Similarity	NPC7165
0.7941	Intermediate Similarity	NPC114159
0.7941	Intermediate Similarity	NPC191412
0.7941	Intermediate Similarity	NPC6818
0.7938	Intermediate Similarity	NPC82902
0.7928	Intermediate Similarity	NPC71348
0.7928	Intermediate Similarity	NPC207251
0.7928	Intermediate Similarity	NPC280782
0.7925	Intermediate Similarity	NPC477054
0.7921	Intermediate Similarity	NPC187722

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 NPC472227 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	1645
0.2-0.3	4245
0.3-0.4	2131
0.4-0.5	484
0.5-0.6	162
0.6-0.7	159
0.7-0.8	134
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8426	Intermediate Similarity	NPD6882	Approved
0.8396	Intermediate Similarity	NPD7320	Approved
0.8384	Intermediate Similarity	NPD6399	Phase 3
0.8381	Intermediate Similarity	NPD6675	Approved
0.8381	Intermediate Similarity	NPD7128	Approved
0.8381	Intermediate Similarity	NPD5739	Approved
0.8381	Intermediate Similarity	NPD6402	Approved
0.8318	Intermediate Similarity	NPD6372	Approved
0.8318	Intermediate Similarity	NPD6373	Approved
0.8224	Intermediate Similarity	NPD6899	Approved
0.8224	Intermediate Similarity	NPD6881	Approved
0.8218	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD6649	Approved
0.8165	Intermediate Similarity	NPD6650	Approved
0.8131	Intermediate Similarity	NPD5697	Approved
0.8131	Intermediate Similarity	NPD5701	Approved
0.8073	Intermediate Similarity	NPD7290	Approved
0.8073	Intermediate Similarity	NPD7102	Approved
0.8073	Intermediate Similarity	NPD6883	Approved
0.8058	Intermediate Similarity	NPD6083	Phase 2
0.8058	Intermediate Similarity	NPD6084	Phase 2
0.8056	Intermediate Similarity	NPD6011	Approved
0.8037	Intermediate Similarity	NPD6008	Approved
0.802	Intermediate Similarity	NPD4202	Approved
0.8	Intermediate Similarity	NPD6869	Approved
0.8	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD6617	Approved
0.8	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6847	Approved
0.7982	Intermediate Similarity	NPD6013	Approved
0.7982	Intermediate Similarity	NPD6014	Approved
0.7982	Intermediate Similarity	NPD6012	Approved
0.7966	Intermediate Similarity	NPD7078	Approved
0.7949	Intermediate Similarity	NPD7492	Approved
0.7928	Intermediate Similarity	NPD8297	Approved
0.7921	Intermediate Similarity	NPD8034	Phase 2
0.7921	Intermediate Similarity	NPD8035	Phase 2
0.7913	Intermediate Similarity	NPD6054	Approved
0.7913	Intermediate Similarity	NPD6059	Approved
0.7885	Intermediate Similarity	NPD4755	Approved
0.7881	Intermediate Similarity	NPD6616	Approved
0.7815	Intermediate Similarity	NPD8293	Discontinued
0.781	Intermediate Similarity	NPD5696	Approved
0.7807	Intermediate Similarity	NPD6009	Approved
0.78	Intermediate Similarity	NPD6903	Approved
0.7778	Intermediate Similarity	NPD6409	Approved
0.7778	Intermediate Similarity	NPD3618	Phase 1
0.7778	Intermediate Similarity	NPD6684	Approved
0.7778	Intermediate Similarity	NPD5330	Approved
0.7778	Intermediate Similarity	NPD7334	Approved
0.7778	Intermediate Similarity	NPD6370	Approved
0.7778	Intermediate Similarity	NPD7146	Approved
0.7778	Intermediate Similarity	NPD7521	Approved
0.7767	Intermediate Similarity	NPD6001	Approved
0.7755	Intermediate Similarity	NPD4786	Approved
0.775	Intermediate Similarity	NPD7736	Approved
0.7736	Intermediate Similarity	NPD4700	Approved
0.7736	Intermediate Similarity	NPD4696	Approved
0.7736	Intermediate Similarity	NPD5285	Approved
0.7736	Intermediate Similarity	NPD5286	Approved
0.7723	Intermediate Similarity	NPD5328	Approved
0.7714	Intermediate Similarity	NPD7902	Approved
0.7692	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5695	Phase 3
0.7692	Intermediate Similarity	NPD6016	Approved
0.7692	Intermediate Similarity	NPD6015	Approved
0.7677	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD5223	Approved
0.7642	Intermediate Similarity	NPD7638	Approved
0.7636	Intermediate Similarity	NPD6412	Phase 2
0.7627	Intermediate Similarity	NPD5988	Approved
0.7624	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6098	Approved
0.7596	Intermediate Similarity	NPD7748	Approved
0.7593	Intermediate Similarity	NPD5224	Approved
0.7593	Intermediate Similarity	NPD5225	Approved
0.7593	Intermediate Similarity	NPD5226	Approved
0.7593	Intermediate Similarity	NPD4633	Approved
0.7593	Intermediate Similarity	NPD5211	Phase 2
0.7586	Intermediate Similarity	NPD6335	Approved
0.7583	Intermediate Similarity	NPD7507	Approved
0.7576	Intermediate Similarity	NPD3665	Phase 1
0.7576	Intermediate Similarity	NPD3666	Approved
0.7576	Intermediate Similarity	NPD3133	Approved
0.7573	Intermediate Similarity	NPD6079	Approved
0.7573	Intermediate Similarity	NPD5281	Approved
0.7573	Intermediate Similarity	NPD7515	Phase 2
0.7573	Intermediate Similarity	NPD5284	Approved
0.757	Intermediate Similarity	NPD7639	Approved
0.757	Intermediate Similarity	NPD7640	Approved
0.7565	Intermediate Similarity	NPD6274	Approved
0.7551	Intermediate Similarity	NPD3667	Approved
0.7549	Intermediate Similarity	NPD6904	Approved
0.7549	Intermediate Similarity	NPD6080	Approved
0.7549	Intermediate Similarity	NPD4753	Phase 2
0.7549	Intermediate Similarity	NPD6673	Approved
0.7544	Intermediate Similarity	NPD4632	Approved
0.7526	Intermediate Similarity	NPD7525	Registered
0.7523	Intermediate Similarity	NPD5175	Approved
0.7523	Intermediate Similarity	NPD4754	Approved
0.7523	Intermediate Similarity	NPD5174	Approved
0.7521	Intermediate Similarity	NPD7101	Approved
0.7521	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD6317	Approved
0.7476	Intermediate Similarity	NPD5207	Approved
0.7459	Intermediate Similarity	NPD6033	Approved
0.7455	Intermediate Similarity	NPD5141	Approved
0.7453	Intermediate Similarity	NPD4697	Phase 3
0.7451	Intermediate Similarity	NPD6672	Approved
0.7451	Intermediate Similarity	NPD5737	Approved
0.7436	Intermediate Similarity	NPD6314	Approved
0.7436	Intermediate Similarity	NPD6313	Approved
0.7429	Intermediate Similarity	NPD7900	Approved
0.7429	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6067	Discontinued
0.7398	Intermediate Similarity	NPD7319	Approved
0.7395	Intermediate Similarity	NPD6908	Approved
0.7395	Intermediate Similarity	NPD6909	Approved
0.7387	Intermediate Similarity	NPD4767	Approved
0.7387	Intermediate Similarity	NPD4768	Approved
0.7374	Intermediate Similarity	NPD4221	Approved
0.7374	Intermediate Similarity	NPD4223	Phase 3
0.7358	Intermediate Similarity	NPD4629	Approved
0.7358	Intermediate Similarity	NPD5210	Approved
0.735	Intermediate Similarity	NPD7115	Discovery
0.7327	Intermediate Similarity	NPD5329	Approved
0.7311	Intermediate Similarity	NPD6319	Approved
0.729	Intermediate Similarity	NPD5222	Approved
0.729	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5221	Approved
0.7288	Intermediate Similarity	NPD7327	Approved
0.7288	Intermediate Similarity	NPD7328	Approved
0.7282	Intermediate Similarity	NPD5208	Approved
0.7273	Intermediate Similarity	NPD7604	Phase 2
0.7257	Intermediate Similarity	NPD5128	Approved
0.7257	Intermediate Similarity	NPD4730	Approved
0.7257	Intermediate Similarity	NPD4729	Approved
0.7255	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5983	Phase 2
0.7238	Intermediate Similarity	NPD5693	Phase 1
0.7238	Intermediate Similarity	NPD6050	Approved
0.7228	Intermediate Similarity	NPD4197	Approved
0.7227	Intermediate Similarity	NPD7516	Approved
0.7222	Intermediate Similarity	NPD5173	Approved
0.7216	Intermediate Similarity	NPD6116	Phase 1
0.7212	Intermediate Similarity	NPD6051	Approved
0.7207	Intermediate Similarity	NPD6052	Approved
0.7193	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8377	Approved
0.7167	Intermediate Similarity	NPD8294	Approved
0.7154	Intermediate Similarity	NPD6336	Discontinued
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.713	Intermediate Similarity	NPD4634	Approved
0.713	Intermediate Similarity	NPD5249	Phase 3
0.713	Intermediate Similarity	NPD5251	Approved
0.713	Intermediate Similarity	NPD5250	Approved
0.713	Intermediate Similarity	NPD5169	Approved
0.713	Intermediate Similarity	NPD5247	Approved
0.713	Intermediate Similarity	NPD5248	Approved
0.713	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5135	Approved
0.7129	Intermediate Similarity	NPD4788	Approved
0.7119	Intermediate Similarity	NPD6868	Approved
0.7113	Intermediate Similarity	NPD6117	Approved
0.7113	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8335	Approved
0.7107	Intermediate Similarity	NPD8379	Approved
0.7107	Intermediate Similarity	NPD8378	Approved
0.7107	Intermediate Similarity	NPD8296	Approved
0.7107	Intermediate Similarity	NPD8380	Approved
0.7107	Intermediate Similarity	NPD8033	Approved
0.7094	Intermediate Similarity	NPD8133	Approved
0.7087	Intermediate Similarity	NPD4693	Phase 3
0.7087	Intermediate Similarity	NPD4689	Approved
0.7087	Intermediate Similarity	NPD4688	Approved
0.7087	Intermediate Similarity	NPD4138	Approved
0.7087	Intermediate Similarity	NPD5205	Approved
0.7087	Intermediate Similarity	NPD4690	Approved
0.7075	Intermediate Similarity	NPD5694	Approved
0.7069	Intermediate Similarity	NPD5215	Approved
0.7069	Intermediate Similarity	NPD5216	Approved
0.7069	Intermediate Similarity	NPD5127	Approved
0.7069	Intermediate Similarity	NPD5217	Approved
0.7059	Intermediate Similarity	NPD3668	Phase 3
0.701	Intermediate Similarity	NPD6942	Approved
0.701	Intermediate Similarity	NPD7339	Approved
0.7009	Intermediate Similarity	NPD6053	Discontinued
0.697	Remote Similarity	NPD6118	Approved
0.697	Remote Similarity	NPD6697	Approved
0.697	Remote Similarity	NPD6114	Approved
0.697	Remote Similarity	NPD6115	Approved
0.6967	Remote Similarity	NPD7503	Approved
0.6964	Remote Similarity	NPD7632	Discontinued
0.6961	Remote Similarity	NPD5362	Discontinued
0.6957	Remote Similarity	NPD6686	Approved
0.6931	Remote Similarity	NPD5369	Approved
0.6923	Remote Similarity	NPD5690	Phase 2
0.6923	Remote Similarity	NPD5279	Phase 3
0.6923	Remote Similarity	NPD4694	Approved
0.6923	Remote Similarity	NPD5280	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