NPASS Compound

Structure

NPC1753 OpenBabel07101718202D 34 38 0 0 1 0 0 0 0 0999 V2000 -3.6275 -0.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1483 0.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3496 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8625 -1.1049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3753 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6876 -1.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3753 -1.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 1 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 4.8368 -1.1049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 -3.4103 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 6 29 1 0 0 0 0 7 8 1 0 0 0 0 7 19 2 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 27 1 0 0 0 0 12 29 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 17 25 1 0 0 0 0 18 28 1 0 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 20 26 1 6 0 0 0 21 27 1 1 0 0 0 21 28 1 0 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 28 1 0 0 0 0 23 32 2 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 30 1 6 0 0 0 30 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	511.905
LogP:	4.833
LogD:	4.277
LogS:	-4.605
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.457
Synthetic Accessibility Score:	4.889
Fsp3:	0.867
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:	-5.396
MDCK Permeability:	2.2270998670137487e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.856
30% Bioavailability (F30%):	0.794

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	95.31864166259766%
Volume Distribution (VD):	0.775
Pgp-substrate:	2.5541958808898926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.429
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.193
CYP2C9-substrate:	0.85
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.394
CYP3A4-inhibitor:	0.272
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	2.961
Half-life (T1/2):	0.609

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.178
Skin Sensitization:	0.114
Carcinogencity:	0.022
Eye Corrosion:	0.019
Eye Irritation:	0.636
Respiratory Toxicity:	0.369

Download Data

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

Natural Product: NPC1753

Natural Product ID:	NPC1753
*Common Name:**	23-Hydroxy-3-Oxoolean-12-En-27-Oic Acid
IUPAC Name:	(4aR,6aR,6aR,6bR,8aR,9R,12aR,14bR)-9-(hydroxymethyl)-2,2,4a,6b,9,12a-hexamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-6a-carboxylic acid
Synonyms:
Standard InCHIKey:	OACHIIJBVSXTEJ-VRKDNAIFSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-25(2)13-14-26(3)15-16-30(24(33)34)19(20(26)17-25)7-8-22-27(4)11-10-23(32)28(5,18-31)21(27)9-12-29(22,30)6/h7,20-22,31H,8-18H2,1-6H3,(H,33,34)/t20-,21+,22+,26+,27-,28-,29+,30+/m0/s1
SMILES:	CC1(C)CC[C@]2(C)CC[C@@]3(C(=CC[C@@H]4[C@@]5(C)CCC(=O)[C@@](C)(CO)[C@@H]5CC[C@@]34C)[C@@H]2C1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081158
PubChem CID:	23651015
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
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19618898]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	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

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	39170.0	nM	PMID[529550]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6560.0	nM	PMID[529550]

☑ 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 NPC1753 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	1254
0.2-0.3	5197
0.3-0.4	14471
0.4-0.5	8819
0.5-0.6	5907
0.6-0.7	4759
0.7-0.8	1657
0.8-0.85	161
0.85-0.9	169
0.9-0.95	99
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474511
0.9878	High Similarity	NPC158141
0.9878	High Similarity	NPC173089
0.9643	High Similarity	NPC474700
0.9425	High Similarity	NPC148964
0.9419	High Similarity	NPC471588
0.9419	High Similarity	NPC6255
0.9294	High Similarity	NPC474474
0.9268	High Similarity	NPC69101
0.9268	High Similarity	NPC310989
0.9268	High Similarity	NPC251779
0.9205	High Similarity	NPC209868
0.9205	High Similarity	NPC474529
0.9195	High Similarity	NPC288833
0.9195	High Similarity	NPC155120
0.9195	High Similarity	NPC324341
0.9195	High Similarity	NPC228784
0.9195	High Similarity	NPC282616
0.9195	High Similarity	NPC38754
0.9195	High Similarity	NPC966
0.9186	High Similarity	NPC143232
0.9186	High Similarity	NPC198664
0.9186	High Similarity	NPC274330
0.9186	High Similarity	NPC281524
0.9146	High Similarity	NPC267691
0.9146	High Similarity	NPC3915
0.9146	High Similarity	NPC162632
0.9146	High Similarity	NPC274050
0.9146	High Similarity	NPC263272
0.9101	High Similarity	NPC148523
0.9091	High Similarity	NPC298554
0.908	High Similarity	NPC111110
0.908	High Similarity	NPC193750
0.908	High Similarity	NPC291028
0.908	High Similarity	NPC470589
0.908	High Similarity	NPC172361
0.908	High Similarity	NPC86372
0.908	High Similarity	NPC46441
0.908	High Similarity	NPC126369
0.907	High Similarity	NPC290690
0.907	High Similarity	NPC52169
0.907	High Similarity	NPC470629
0.907	High Similarity	NPC181225
0.907	High Similarity	NPC474512
0.907	High Similarity	NPC473242
0.907	High Similarity	NPC17733
0.907	High Similarity	NPC182797
0.9048	High Similarity	NPC96095
0.9048	High Similarity	NPC180834
0.9	High Similarity	NPC98874
0.9	High Similarity	NPC132824
0.8989	High Similarity	NPC222047
0.8977	High Similarity	NPC158030
0.8977	High Similarity	NPC187722
0.8977	High Similarity	NPC233455
0.8977	High Similarity	NPC65120
0.8977	High Similarity	NPC4036
0.8977	High Similarity	NPC105189
0.8977	High Similarity	NPC145067
0.8977	High Similarity	NPC474525
0.8966	High Similarity	NPC225585
0.8966	High Similarity	NPC25906
0.8966	High Similarity	NPC477973
0.8966	High Similarity	NPC127689
0.8966	High Similarity	NPC61543
0.8966	High Similarity	NPC130520
0.8966	High Similarity	NPC263393
0.8966	High Similarity	NPC234346
0.8966	High Similarity	NPC290972
0.8966	High Similarity	NPC121798
0.8966	High Similarity	NPC270768
0.8966	High Similarity	NPC64872
0.8966	High Similarity	NPC59263
0.8966	High Similarity	NPC293048
0.8966	High Similarity	NPC470588
0.8953	High Similarity	NPC71507
0.8953	High Similarity	NPC18064
0.8953	High Similarity	NPC242468
0.8953	High Similarity	NPC98442
0.8953	High Similarity	NPC51700
0.8953	High Similarity	NPC96496
0.8953	High Similarity	NPC142415
0.8953	High Similarity	NPC130577
0.8953	High Similarity	NPC307426
0.8953	High Similarity	NPC293564
0.8953	High Similarity	NPC102683
0.8953	High Similarity	NPC68160
0.8953	High Similarity	NPC171203
0.8953	High Similarity	NPC88716
0.8929	High Similarity	NPC200752
0.8929	High Similarity	NPC70834
0.8902	High Similarity	NPC16394
0.8902	High Similarity	NPC199595
0.8901	High Similarity	NPC187933
0.8889	High Similarity	NPC195715
0.8876	High Similarity	NPC295643
0.8876	High Similarity	NPC214756
0.8876	High Similarity	NPC118490
0.8876	High Similarity	NPC158059
0.8876	High Similarity	NPC229281
0.8876	High Similarity	NPC118519
0.8876	High Similarity	NPC202728
0.8876	High Similarity	NPC272075
0.8864	High Similarity	NPC7260
0.8864	High Similarity	NPC227467
0.8864	High Similarity	NPC477872
0.8864	High Similarity	NPC474728
0.8864	High Similarity	NPC210037
0.8864	High Similarity	NPC290614
0.8864	High Similarity	NPC130278
0.8864	High Similarity	NPC18872
0.8864	High Similarity	NPC198818
0.8864	High Similarity	NPC120968
0.8864	High Similarity	NPC273621
0.8851	High Similarity	NPC246708
0.8851	High Similarity	NPC40552
0.8837	High Similarity	NPC72638
0.8837	High Similarity	NPC324063
0.8837	High Similarity	NPC56588
0.8824	High Similarity	NPC312660
0.8804	High Similarity	NPC111214
0.8804	High Similarity	NPC271614
0.8804	High Similarity	NPC174663
0.8804	High Similarity	NPC29765
0.8795	High Similarity	NPC267517
0.8795	High Similarity	NPC37038
0.8795	High Similarity	NPC104545
0.8791	High Similarity	NPC201657
0.8791	High Similarity	NPC157113
0.8791	High Similarity	NPC62516
0.878	High Similarity	NPC110094
0.878	High Similarity	NPC260385
0.878	High Similarity	NPC280654
0.8778	High Similarity	NPC159365
0.8778	High Similarity	NPC87095
0.8778	High Similarity	NPC184006
0.8778	High Similarity	NPC6818
0.8778	High Similarity	NPC114159
0.8778	High Similarity	NPC191412
0.8778	High Similarity	NPC78580
0.8778	High Similarity	NPC23621
0.8764	High Similarity	NPC84319
0.8764	High Similarity	NPC235884
0.8764	High Similarity	NPC285184
0.8764	High Similarity	NPC71074
0.8764	High Similarity	NPC52021
0.8764	High Similarity	NPC470590
0.8764	High Similarity	NPC300351
0.8764	High Similarity	NPC77099
0.8764	High Similarity	NPC306541
0.8764	High Similarity	NPC60755
0.8764	High Similarity	NPC472149
0.8764	High Similarity	NPC25299
0.875	High Similarity	NPC161751
0.875	High Similarity	NPC474686
0.875	High Similarity	NPC474972
0.875	High Similarity	NPC95246
0.875	High Similarity	NPC69627
0.8736	High Similarity	NPC73064
0.8721	High Similarity	NPC201655
0.8721	High Similarity	NPC133954
0.8721	High Similarity	NPC274724
0.871	High Similarity	NPC35239
0.8696	High Similarity	NPC261935
0.8696	High Similarity	NPC21728
0.8696	High Similarity	NPC106112
0.8696	High Similarity	NPC26413
0.869	High Similarity	NPC471898
0.8681	High Similarity	NPC139570
0.8681	High Similarity	NPC23241
0.8681	High Similarity	NPC473240
0.8681	High Similarity	NPC96916
0.8675	High Similarity	NPC231431
0.8667	High Similarity	NPC136313
0.8667	High Similarity	NPC307335
0.8667	High Similarity	NPC133579
0.8667	High Similarity	NPC86368
0.8667	High Similarity	NPC169343
0.8667	High Similarity	NPC474806
0.8667	High Similarity	NPC74855
0.8667	High Similarity	NPC275809
0.8659	High Similarity	NPC471897
0.8659	High Similarity	NPC471899
0.8659	High Similarity	NPC107039
0.8652	High Similarity	NPC113989
0.8652	High Similarity	NPC49320
0.8652	High Similarity	NPC120840
0.8621	High Similarity	NPC475862
0.8621	High Similarity	NPC74363
0.8621	High Similarity	NPC213412
0.8602	High Similarity	NPC164349
0.8602	High Similarity	NPC188833
0.8587	High Similarity	NPC259733
0.8587	High Similarity	NPC327179
0.8587	High Similarity	NPC173744
0.8587	High Similarity	NPC116457
0.8587	High Similarity	NPC476327
0.8587	High Similarity	NPC204961
0.8587	High Similarity	NPC167193
0.8587	High Similarity	NPC158371

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 NPC1753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1640
0.2-0.3	3821
0.3-0.4	2368
0.4-0.5	679
0.5-0.6	217
0.6-0.7	202
0.7-0.8	38
0.8-0.85	3
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8977	High Similarity	NPD7515	Phase 2
0.8571	High Similarity	NPD7748	Approved
0.8333	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD7902	Approved
0.8182	Intermediate Similarity	NPD4786	Approved
0.8161	Intermediate Similarity	NPD3667	Approved
0.8065	Intermediate Similarity	NPD6399	Phase 3
0.7979	Intermediate Similarity	NPD7900	Approved
0.7979	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3665	Phase 1
0.7778	Intermediate Similarity	NPD3666	Approved
0.7778	Intermediate Similarity	NPD3133	Approved
0.7766	Intermediate Similarity	NPD6411	Approved
0.7732	Intermediate Similarity	NPD6083	Phase 2
0.7732	Intermediate Similarity	NPD6084	Phase 2
0.7727	Intermediate Similarity	NPD4695	Discontinued
0.7634	Intermediate Similarity	NPD6672	Approved
0.7634	Intermediate Similarity	NPD5737	Approved
0.7629	Intermediate Similarity	NPD7614	Phase 1
0.7614	Intermediate Similarity	NPD7645	Phase 2
0.7609	Intermediate Similarity	NPD6409	Approved
0.7609	Intermediate Similarity	NPD5330	Approved
0.7609	Intermediate Similarity	NPD6684	Approved
0.7609	Intermediate Similarity	NPD7521	Approved
0.7609	Intermediate Similarity	NPD3618	Phase 1
0.7609	Intermediate Similarity	NPD7334	Approved
0.7609	Intermediate Similarity	NPD7146	Approved
0.7582	Intermediate Similarity	NPD3668	Phase 3
0.7553	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD4753	Phase 2
0.7553	Intermediate Similarity	NPD6101	Approved
0.7553	Intermediate Similarity	NPD5328	Approved
0.7447	Intermediate Similarity	NPD6903	Approved
0.7419	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD8034	Phase 2
0.7396	Intermediate Similarity	NPD8035	Phase 2
0.7396	Intermediate Similarity	NPD6079	Approved
0.7363	Intermediate Similarity	NPD4221	Approved
0.7363	Intermediate Similarity	NPD4223	Phase 3
0.7347	Intermediate Similarity	NPD5695	Phase 3
0.7312	Intermediate Similarity	NPD5329	Approved
0.73	Intermediate Similarity	NPD5696	Approved
0.7283	Intermediate Similarity	NPD4788	Approved
0.7273	Intermediate Similarity	NPD7732	Phase 3
0.7234	Intermediate Similarity	NPD5279	Phase 3
0.7234	Intermediate Similarity	NPD6098	Approved
0.7216	Intermediate Similarity	NPD5281	Approved
0.7216	Intermediate Similarity	NPD5284	Approved
0.7212	Intermediate Similarity	NPD7128	Approved
0.7212	Intermediate Similarity	NPD5739	Approved
0.7212	Intermediate Similarity	NPD6675	Approved
0.7212	Intermediate Similarity	NPD6402	Approved
0.7204	Intermediate Similarity	NPD4197	Approved
0.7188	Intermediate Similarity	NPD6080	Approved
0.7188	Intermediate Similarity	NPD6673	Approved
0.7188	Intermediate Similarity	NPD6904	Approved
0.7182	Intermediate Similarity	NPD7115	Discovery
0.7172	Intermediate Similarity	NPD4629	Approved
0.7172	Intermediate Similarity	NPD5210	Approved
0.7159	Intermediate Similarity	NPD7339	Approved
0.7159	Intermediate Similarity	NPD6942	Approved
0.7158	Intermediate Similarity	NPD3573	Approved
0.7143	Intermediate Similarity	NPD5779	Approved
0.7143	Intermediate Similarity	NPD4202	Approved
0.7143	Intermediate Similarity	NPD5778	Approved
0.7129	Intermediate Similarity	NPD7638	Approved
0.7111	Intermediate Similarity	NPD3617	Approved
0.7105	Intermediate Similarity	NPD8328	Phase 3
0.71	Intermediate Similarity	NPD5222	Approved
0.71	Intermediate Similarity	NPD4697	Phase 3
0.71	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5221	Approved
0.7079	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7320	Approved
0.7075	Intermediate Similarity	NPD6881	Approved
0.7075	Intermediate Similarity	NPD6899	Approved
0.7065	Intermediate Similarity	NPD5369	Approved
0.7059	Intermediate Similarity	NPD7640	Approved
0.7059	Intermediate Similarity	NPD7639	Approved
0.7053	Intermediate Similarity	NPD4689	Approved
0.7053	Intermediate Similarity	NPD5205	Approved
0.7053	Intermediate Similarity	NPD4138	Approved
0.7053	Intermediate Similarity	NPD4623	Approved
0.7053	Intermediate Similarity	NPD4519	Discontinued
0.7053	Intermediate Similarity	NPD4690	Approved
0.7053	Intermediate Similarity	NPD4688	Approved
0.7053	Intermediate Similarity	NPD4693	Phase 3
0.703	Intermediate Similarity	NPD5173	Approved
0.703	Intermediate Similarity	NPD4755	Approved
0.7027	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6372	Approved
0.7009	Intermediate Similarity	NPD6373	Approved
0.7	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4270	Approved
0.6989	Remote Similarity	NPD4269	Approved
0.6981	Remote Similarity	NPD5697	Approved
0.6981	Remote Similarity	NPD6412	Phase 2
0.6981	Remote Similarity	NPD5701	Approved
0.6957	Remote Similarity	NPD7525	Registered
0.6944	Remote Similarity	NPD7290	Approved
0.6944	Remote Similarity	NPD6883	Approved
0.6944	Remote Similarity	NPD7102	Approved
0.6923	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6011	Approved
0.6907	Remote Similarity	NPD5208	Approved
0.6893	Remote Similarity	NPD5286	Approved
0.6893	Remote Similarity	NPD5285	Approved
0.6893	Remote Similarity	NPD4700	Approved
0.6893	Remote Similarity	NPD4696	Approved
0.6889	Remote Similarity	NPD6117	Approved
0.6881	Remote Similarity	NPD6869	Approved
0.6881	Remote Similarity	NPD8130	Phase 1
0.6881	Remote Similarity	NPD6649	Approved
0.6881	Remote Similarity	NPD6650	Approved
0.6881	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6847	Approved
0.6881	Remote Similarity	NPD6617	Approved
0.6875	Remote Similarity	NPD5280	Approved
0.6875	Remote Similarity	NPD5690	Phase 2
0.6875	Remote Similarity	NPD4694	Approved
0.6869	Remote Similarity	NPD6050	Approved
0.6869	Remote Similarity	NPD7637	Suspended
0.6869	Remote Similarity	NPD5693	Phase 1
0.6854	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6014	Approved
0.6852	Remote Similarity	NPD6012	Approved
0.6852	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6013	Approved
0.6827	Remote Similarity	NPD5223	Approved
0.6824	Remote Similarity	NPD4224	Phase 2
0.6818	Remote Similarity	NPD6081	Approved
0.6818	Remote Similarity	NPD8297	Approved
0.6818	Remote Similarity	NPD6882	Approved
0.6813	Remote Similarity	NPD6116	Phase 1
0.6796	Remote Similarity	NPD4225	Approved
0.6782	Remote Similarity	NPD4137	Phase 3
0.6774	Remote Similarity	NPD4252	Approved
0.6771	Remote Similarity	NPD5363	Approved
0.6768	Remote Similarity	NPD5692	Phase 3
0.6768	Remote Similarity	NPD5785	Approved
0.6762	Remote Similarity	NPD5225	Approved
0.6762	Remote Similarity	NPD5224	Approved
0.6762	Remote Similarity	NPD4633	Approved
0.6762	Remote Similarity	NPD5211	Phase 2
0.6762	Remote Similarity	NPD5226	Approved
0.6739	Remote Similarity	NPD6114	Approved
0.6739	Remote Similarity	NPD6115	Approved
0.6739	Remote Similarity	NPD6697	Approved
0.6739	Remote Similarity	NPD6118	Approved
0.6705	Remote Similarity	NPD4747	Approved
0.6705	Remote Similarity	NPD4244	Approved
0.6705	Remote Similarity	NPD4245	Approved
0.6705	Remote Similarity	NPD4789	Approved
0.6705	Remote Similarity	NPD4691	Approved
0.6702	Remote Similarity	NPD4139	Approved
0.6702	Remote Similarity	NPD4692	Approved
0.6701	Remote Similarity	NPD5786	Approved
0.67	Remote Similarity	NPD5694	Approved
0.6698	Remote Similarity	NPD5174	Approved
0.6698	Remote Similarity	NPD4754	Approved
0.6698	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6637	Remote Similarity	NPD6868	Approved
0.6636	Remote Similarity	NPD5141	Approved
0.6636	Remote Similarity	NPD4634	Approved
0.6629	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4243	Approved
0.6629	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4632	Approved
0.6606	Remote Similarity	NPD6686	Approved
0.66	Remote Similarity	NPD5207	Approved
0.6596	Remote Similarity	NPD5368	Approved
0.6596	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3698	Phase 2
0.6591	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7736	Approved
0.6574	Remote Similarity	NPD4767	Approved
0.6574	Remote Similarity	NPD6008	Approved
0.6574	Remote Similarity	NPD4768	Approved
0.6569	Remote Similarity	NPD6001	Approved
0.6562	Remote Similarity	NPD5362	Discontinued
0.6552	Remote Similarity	NPD6319	Approved
0.6526	Remote Similarity	NPD8028	Phase 2
0.6522	Remote Similarity	NPD6933	Approved
0.6522	Remote Similarity	NPD6335	Approved
0.6512	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6051	Approved
0.6491	Remote Similarity	NPD6274	Approved
0.6484	Remote Similarity	NPD5733	Approved
0.6484	Remote Similarity	NPD4058	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