NPASS Compound

Structure

NPC471932 OpenBabel07101718322D 35 36 0 0 1 0 0 0 0 0999 V2000 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2574 2.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 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 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2793 2.4190 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 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 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 0.0000 -1.0000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6102 3.1622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 1.4680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 7 17 2 0 0 0 0 9 19 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 12 22 1 0 0 0 0 13 21 1 0 0 0 0 16 6 1 1 0 0 0 16 28 1 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 18 8 1 6 0 0 0 18 33 1 0 0 0 0 19 29 2 0 0 0 0 19 33 1 0 0 0 0 20 13 1 6 0 0 0 20 25 1 0 0 0 0 21 24 1 0 0 0 0 21 30 2 0 0 0 0 22 31 2 0 0 0 0 22 34 1 0 0 0 0 23 14 1 6 0 0 0 23 25 1 0 0 0 0 23 27 1 0 0 0 0 24 18 1 6 0 0 0 24 25 1 0 0 0 0 26 27 1 0 0 0 0 26 34 1 0 0 0 0 27 35 1 0 0 0 0 28 32 2 0 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.29
Volume:	521.444
LogP:	4.056
LogD:	2.801
LogS:	-3.844
# Rotatable Bonds:	12
TPSA:	95.97
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.198
Synthetic Accessibility Score:	5.085
Fsp3:	0.714
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:	-4.704
MDCK Permeability:	6.413027585949749e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.556

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	81.06432342529297%
Volume Distribution (VD):	1.853
Pgp-substrate:	11.019388198852539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.382
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.78
CYP2C19-substrate:	0.729
CYP2C9-inhibitor:	0.934
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.926
CYP3A4-substrate:	0.536

ADMET: Excretion

Clearance (CL):	4.786
Half-life (T1/2):	0.493

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.94
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.431
Maximum Recommended Daily Dose:	0.132
Skin Sensitization:	0.098
Carcinogencity:	0.081
Eye Corrosion:	0.065
Eye Irritation:	0.019
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC471932

Natural Product ID:	NPC471932
*Common Name:**	(1R,4R,5S,6R,7S,8R,9S,2''s,2'''e)-4-Acetoxy-8-(2''-Methylbutanoyloxy)-9-(3'''-Methyl-2'''-Pentenoyloxy)-10(14)-Oplopen-3-One
IUPAC Name:	[(1S,3aR,5S,6R,7S,7aR)-1-[(1R)-1-acetyloxyethyl]-6-[(2S)-2-methylbutanoyl]oxy-4-methylidene-2-oxo-7-propan-2-yl-3,3a,5,6,7,7a-hexahydro-1H-inden-5-yl] (E)-3-methylpent-2-enoate
Synonyms:
Standard InCHIKey:	ZAHNEGFDQRIZHX-WZRMXTHLSA-N
Standard InCHI:	InChI=1S/C28H42O7/c1-10-15(5)12-22(31)34-26-17(7)20-13-21(30)24(18(8)33-19(9)29)25(20)23(14(3)4)27(26)35-28(32)16(6)11-2/h12,14,16,18,20,23-27H,7,10-11,13H2,1-6,8-9H3/b15-12+/t16-,18+,20-,23-,24-,25+,26-,27+/m0/s1
SMILES:	CC[C@@H](C(=O)O[C@H]1[C@@H](OC(=O)/C=C(/CC)C)C(=C)[C@H]2[C@H]([C@@H]1C(C)C)[C@@H]([C@H](OC(=O)C)C)C(=O)C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3298989
PubChem CID:	90683359
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO27190	Pittocaulon filare	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24842703]
NPO27190	Pittocaulon filare	Species	Asteraceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.17	umol	PMID[458472]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	12.67	%	PMID[458472]

☑ 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 NPC471932 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	217
0.1-0.2	1300
0.2-0.3	4211
0.3-0.4	7544
0.4-0.5	13818
0.5-0.6	8092
0.6-0.7	5881
0.7-0.8	1605
0.8-0.85	16
0.85-0.9	7
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9381	High Similarity	NPC103088
0.9381	High Similarity	NPC470979
0.9381	High Similarity	NPC470975
0.9149	High Similarity	NPC118159
0.8835	High Similarity	NPC471933
0.8687	High Similarity	NPC475750
0.8544	High Similarity	NPC471934
0.8265	Intermediate Similarity	NPC470974
0.8265	Intermediate Similarity	NPC470978
0.8224	Intermediate Similarity	NPC470120
0.8182	Intermediate Similarity	NPC475520
0.8144	Intermediate Similarity	NPC233437
0.8144	Intermediate Similarity	NPC207641
0.8144	Intermediate Similarity	NPC221282
0.8144	Intermediate Similarity	NPC472953
0.8125	Intermediate Similarity	NPC269642
0.8125	Intermediate Similarity	NPC170538
0.8091	Intermediate Similarity	NPC473720
0.8053	Intermediate Similarity	NPC11895
0.8041	Intermediate Similarity	NPC161638
0.8039	Intermediate Similarity	NPC475099
0.8018	Intermediate Similarity	NPC475041
0.8	Intermediate Similarity	NPC474716
0.7981	Intermediate Similarity	NPC470297
0.7963	Intermediate Similarity	NPC476801
0.7959	Intermediate Similarity	NPC473944
0.7946	Intermediate Similarity	NPC476961
0.7944	Intermediate Similarity	NPC179642
0.7944	Intermediate Similarity	NPC253906
0.7941	Intermediate Similarity	NPC471413
0.7941	Intermediate Similarity	NPC306856
0.7938	Intermediate Similarity	NPC288699
0.7928	Intermediate Similarity	NPC470420
0.7925	Intermediate Similarity	NPC473482
0.7925	Intermediate Similarity	NPC475418
0.7925	Intermediate Similarity	NPC318363
0.7921	Intermediate Similarity	NPC110937
0.7921	Intermediate Similarity	NPC2049
0.7913	Intermediate Similarity	NPC293112
0.7913	Intermediate Similarity	NPC473635
0.7909	Intermediate Similarity	NPC190286
0.7905	Intermediate Similarity	NPC470980
0.7895	Intermediate Similarity	NPC469789
0.789	Intermediate Similarity	NPC472926
0.7885	Intermediate Similarity	NPC254202
0.7876	Intermediate Similarity	NPC46570
0.7864	Intermediate Similarity	NPC471412
0.7857	Intermediate Similarity	NPC472667
0.7857	Intermediate Similarity	NPC42673
0.7857	Intermediate Similarity	NPC230513
0.785	Intermediate Similarity	NPC273433
0.785	Intermediate Similarity	NPC469370
0.785	Intermediate Similarity	NPC475065
0.7843	Intermediate Similarity	NPC252295
0.7843	Intermediate Similarity	NPC176845
0.7838	Intermediate Similarity	NPC473656
0.7838	Intermediate Similarity	NPC284068
0.783	Intermediate Similarity	NPC180744
0.783	Intermediate Similarity	NPC330011
0.783	Intermediate Similarity	NPC329048
0.783	Intermediate Similarity	NPC133422
0.783	Intermediate Similarity	NPC472925
0.7826	Intermediate Similarity	NPC81736
0.7826	Intermediate Similarity	NPC172154
0.7826	Intermediate Similarity	NPC8369
0.7818	Intermediate Similarity	NPC178289
0.7818	Intermediate Similarity	NPC90472
0.7818	Intermediate Similarity	NPC470953
0.7812	Intermediate Similarity	NPC220478
0.7812	Intermediate Similarity	NPC261253
0.7812	Intermediate Similarity	NPC474045
0.7812	Intermediate Similarity	NPC469676
0.781	Intermediate Similarity	NPC189616
0.7807	Intermediate Similarity	NPC107493
0.78	Intermediate Similarity	NPC148463
0.78	Intermediate Similarity	NPC476716
0.78	Intermediate Similarity	NPC470697
0.7798	Intermediate Similarity	NPC269530
0.7788	Intermediate Similarity	NPC470972
0.7788	Intermediate Similarity	NPC251226
0.7788	Intermediate Similarity	NPC162973
0.7788	Intermediate Similarity	NPC268530
0.7788	Intermediate Similarity	NPC4548
0.7788	Intermediate Similarity	NPC154491
0.7788	Intermediate Similarity	NPC472004
0.7778	Intermediate Similarity	NPC470230
0.7768	Intermediate Similarity	NPC153440
0.7768	Intermediate Similarity	NPC475372
0.7767	Intermediate Similarity	NPC469551
0.7767	Intermediate Similarity	NPC117685
0.7767	Intermediate Similarity	NPC476933
0.7757	Intermediate Similarity	NPC476802
0.7757	Intermediate Similarity	NPC89171
0.7748	Intermediate Similarity	NPC106228
0.7748	Intermediate Similarity	NPC154363
0.7748	Intermediate Similarity	NPC470793
0.7748	Intermediate Similarity	NPC72772
0.7748	Intermediate Similarity	NPC176840
0.7748	Intermediate Similarity	NPC138372
0.7748	Intermediate Similarity	NPC196931
0.7748	Intermediate Similarity	NPC469794
0.7748	Intermediate Similarity	NPC471127
0.7748	Intermediate Similarity	NPC234858
0.7745	Intermediate Similarity	NPC17326
0.7745	Intermediate Similarity	NPC134454
0.7739	Intermediate Similarity	NPC120724
0.7739	Intermediate Similarity	NPC473802
0.7739	Intermediate Similarity	NPC472399
0.7736	Intermediate Similarity	NPC469874
0.7736	Intermediate Similarity	NPC323834
0.7727	Intermediate Similarity	NPC250109
0.7727	Intermediate Similarity	NPC962
0.7727	Intermediate Similarity	NPC473535
0.7719	Intermediate Similarity	NPC310511
0.7719	Intermediate Similarity	NPC4021
0.7719	Intermediate Similarity	NPC67569
0.7719	Intermediate Similarity	NPC159456
0.7714	Intermediate Similarity	NPC475526
0.7714	Intermediate Similarity	NPC329345
0.7714	Intermediate Similarity	NPC473283
0.7712	Intermediate Similarity	NPC472770
0.7712	Intermediate Similarity	NPC231529
0.7706	Intermediate Similarity	NPC470960
0.7699	Intermediate Similarity	NPC312536
0.7699	Intermediate Similarity	NPC5292
0.7699	Intermediate Similarity	NPC476960
0.7699	Intermediate Similarity	NPC305260
0.7699	Intermediate Similarity	NPC270850
0.7692	Intermediate Similarity	NPC472924
0.7692	Intermediate Similarity	NPC287423
0.7692	Intermediate Similarity	NPC42399
0.7692	Intermediate Similarity	NPC310981
0.7679	Intermediate Similarity	NPC472927
0.7679	Intermediate Similarity	NPC476959
0.7679	Intermediate Similarity	NPC55296
0.7679	Intermediate Similarity	NPC470959
0.7679	Intermediate Similarity	NPC10721
0.7679	Intermediate Similarity	NPC53396
0.7679	Intermediate Similarity	NPC98249
0.7679	Intermediate Similarity	NPC469684
0.7679	Intermediate Similarity	NPC476965
0.7677	Intermediate Similarity	NPC152467
0.7677	Intermediate Similarity	NPC8062
0.7672	Intermediate Similarity	NPC473919
0.7672	Intermediate Similarity	NPC473709
0.767	Intermediate Similarity	NPC264378
0.7664	Intermediate Similarity	NPC475587
0.7664	Intermediate Similarity	NPC469558
0.7664	Intermediate Similarity	NPC475510
0.7658	Intermediate Similarity	NPC67259
0.7658	Intermediate Similarity	NPC147912
0.7658	Intermediate Similarity	NPC474181
0.7658	Intermediate Similarity	NPC284915
0.7658	Intermediate Similarity	NPC238667
0.7652	Intermediate Similarity	NPC470265
0.7652	Intermediate Similarity	NPC23786
0.7647	Intermediate Similarity	NPC21302
0.7647	Intermediate Similarity	NPC29952
0.7647	Intermediate Similarity	NPC11396
0.7647	Intermediate Similarity	NPC307164
0.7647	Intermediate Similarity	NPC111684
0.7647	Intermediate Similarity	NPC58052
0.7642	Intermediate Similarity	NPC96268
0.7636	Intermediate Similarity	NPC265391
0.7636	Intermediate Similarity	NPC470063
0.7634	Intermediate Similarity	NPC469690
0.7634	Intermediate Similarity	NPC469620
0.7632	Intermediate Similarity	NPC476962
0.7632	Intermediate Similarity	NPC474585
0.7632	Intermediate Similarity	NPC79579
0.7632	Intermediate Similarity	NPC143755
0.7627	Intermediate Similarity	NPC311534
0.7627	Intermediate Similarity	NPC245094
0.7624	Intermediate Similarity	NPC84893
0.7624	Intermediate Similarity	NPC471078
0.7624	Intermediate Similarity	NPC473280
0.7624	Intermediate Similarity	NPC473431
0.7624	Intermediate Similarity	NPC473435
0.7619	Intermediate Similarity	NPC105725
0.7619	Intermediate Similarity	NPC80781
0.7619	Intermediate Similarity	NPC137430
0.7619	Intermediate Similarity	NPC32577
0.7619	Intermediate Similarity	NPC155332
0.7619	Intermediate Similarity	NPC474709
0.7619	Intermediate Similarity	NPC114540
0.7619	Intermediate Similarity	NPC295791
0.7615	Intermediate Similarity	NPC472215
0.7615	Intermediate Similarity	NPC472214
0.7611	Intermediate Similarity	NPC124676
0.7611	Intermediate Similarity	NPC146280
0.7611	Intermediate Similarity	NPC284707
0.7607	Intermediate Similarity	NPC471939
0.7604	Intermediate Similarity	NPC30486
0.76	Intermediate Similarity	NPC290651
0.76	Intermediate Similarity	NPC165180
0.7596	Intermediate Similarity	NPC474718
0.7596	Intermediate Similarity	NPC470906
0.7596	Intermediate Similarity	NPC54705
0.7596	Intermediate Similarity	NPC477521
0.7596	Intermediate Similarity	NPC476274

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 NPC471932 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1695
0.2-0.3	3672
0.3-0.4	2290
0.4-0.5	832
0.5-0.6	264
0.6-0.7	202
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.767	Intermediate Similarity	NPD7638	Approved
0.7596	Intermediate Similarity	NPD7639	Approved
0.7596	Intermediate Similarity	NPD7640	Approved
0.757	Intermediate Similarity	NPD6008	Approved
0.7522	Intermediate Similarity	NPD7115	Discovery
0.7333	Intermediate Similarity	NPD4225	Approved
0.7273	Intermediate Similarity	NPD7319	Approved
0.7216	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5778	Approved
0.7184	Intermediate Similarity	NPD5779	Approved
0.7179	Intermediate Similarity	NPD6319	Approved
0.7168	Intermediate Similarity	NPD6053	Discontinued
0.7167	Intermediate Similarity	NPD7507	Approved
0.7157	Intermediate Similarity	NPD46	Approved
0.7157	Intermediate Similarity	NPD6698	Approved
0.7129	Intermediate Similarity	NPD6672	Approved
0.7129	Intermediate Similarity	NPD5737	Approved
0.7105	Intermediate Similarity	NPD4632	Approved
0.7103	Intermediate Similarity	NPD6648	Approved
0.71	Intermediate Similarity	NPD6409	Approved
0.71	Intermediate Similarity	NPD7521	Approved
0.71	Intermediate Similarity	NPD7334	Approved
0.71	Intermediate Similarity	NPD7146	Approved
0.71	Intermediate Similarity	NPD6684	Approved
0.71	Intermediate Similarity	NPD5330	Approved
0.7091	Intermediate Similarity	NPD7128	Approved
0.7091	Intermediate Similarity	NPD6402	Approved
0.7091	Intermediate Similarity	NPD5739	Approved
0.7091	Intermediate Similarity	NPD6675	Approved
0.7083	Intermediate Similarity	NPD7492	Approved
0.7059	Intermediate Similarity	NPD5328	Approved
0.7037	Intermediate Similarity	NPD5344	Discontinued
0.7034	Intermediate Similarity	NPD6059	Approved
0.7034	Intermediate Similarity	NPD6054	Approved
0.7027	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6616	Approved
0.7019	Intermediate Similarity	NPD6399	Phase 3
0.7018	Intermediate Similarity	NPD8297	Approved
0.7	Intermediate Similarity	NPD1694	Approved
0.7	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6371	Approved
0.699	Remote Similarity	NPD5785	Approved
0.6972	Remote Similarity	NPD7632	Discontinued
0.6967	Remote Similarity	NPD7078	Approved
0.6967	Remote Similarity	NPD8293	Discontinued
0.6964	Remote Similarity	NPD7320	Approved
0.6964	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6899	Approved
0.6964	Remote Similarity	NPD6881	Approved
0.6964	Remote Similarity	NPD6686	Approved
0.6961	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6903	Approved
0.6931	Remote Similarity	NPD5786	Approved
0.6923	Remote Similarity	NPD7983	Approved
0.6923	Remote Similarity	NPD5693	Phase 1
0.6923	Remote Similarity	NPD6009	Approved
0.6923	Remote Similarity	NPD6079	Approved
0.6917	Remote Similarity	NPD6370	Approved
0.6911	Remote Similarity	NPD7736	Approved
0.6903	Remote Similarity	NPD6372	Approved
0.6903	Remote Similarity	NPD6373	Approved
0.6903	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5697	Approved
0.6875	Remote Similarity	NPD5701	Approved
0.686	Remote Similarity	NPD7604	Phase 2
0.6842	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD7290	Approved
0.6842	Remote Similarity	NPD6883	Approved
0.6842	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6015	Approved
0.6833	Remote Similarity	NPD6016	Approved
0.6833	Remote Similarity	NPD5983	Phase 2
0.6832	Remote Similarity	NPD5363	Approved
0.6814	Remote Similarity	NPD6011	Approved
0.6792	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7748	Approved
0.6792	Remote Similarity	NPD7900	Approved
0.6783	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD8130	Phase 1
0.6783	Remote Similarity	NPD6650	Approved
0.6783	Remote Similarity	NPD6869	Approved
0.6783	Remote Similarity	NPD6847	Approved
0.6783	Remote Similarity	NPD6649	Approved
0.6783	Remote Similarity	NPD6617	Approved
0.6777	Remote Similarity	NPD5988	Approved
0.6762	Remote Similarity	NPD7637	Suspended
0.6754	Remote Similarity	NPD6013	Approved
0.6754	Remote Similarity	NPD6014	Approved
0.6754	Remote Similarity	NPD6012	Approved
0.6748	Remote Similarity	NPD6336	Discontinued
0.6731	Remote Similarity	NPD1695	Approved
0.6731	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6080	Approved
0.6731	Remote Similarity	NPD6904	Approved
0.6731	Remote Similarity	NPD6101	Approved
0.6731	Remote Similarity	NPD6673	Approved
0.6729	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6882	Approved
0.67	Remote Similarity	NPD4269	Approved
0.67	Remote Similarity	NPD4270	Approved
0.6699	Remote Similarity	NPD3573	Approved
0.6696	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.664	Remote Similarity	NPD6033	Approved
0.6634	Remote Similarity	NPD5362	Discontinued
0.6614	Remote Similarity	NPD7260	Phase 2
0.6606	Remote Similarity	NPD6084	Phase 2
0.6606	Remote Similarity	NPD4755	Approved
0.6606	Remote Similarity	NPD5173	Approved
0.6606	Remote Similarity	NPD7902	Approved
0.6606	Remote Similarity	NPD6083	Phase 2
0.6604	Remote Similarity	NPD6050	Approved
0.6604	Remote Similarity	NPD7515	Phase 2
0.6604	Remote Similarity	NPD6411	Approved
0.6602	Remote Similarity	NPD3618	Phase 1
0.66	Remote Similarity	NPD5369	Approved
0.6585	Remote Similarity	NPD8328	Phase 3
0.6583	Remote Similarity	NPD7327	Approved
0.6583	Remote Similarity	NPD7328	Approved
0.6579	Remote Similarity	NPD6412	Phase 2
0.6574	Remote Similarity	NPD5695	Phase 3
0.6571	Remote Similarity	NPD6051	Approved
0.6569	Remote Similarity	NPD4786	Approved
0.6557	Remote Similarity	NPD8517	Approved
0.6557	Remote Similarity	NPD8515	Approved
0.6557	Remote Similarity	NPD8513	Phase 3
0.6557	Remote Similarity	NPD8033	Approved
0.6557	Remote Similarity	NPD8516	Approved
0.6555	Remote Similarity	NPD6868	Approved
0.6535	Remote Similarity	NPD6435	Approved
0.6535	Remote Similarity	NPD5209	Approved
0.6518	Remote Similarity	NPD5211	Phase 2
0.6509	Remote Similarity	NPD7838	Discovery
0.6509	Remote Similarity	NPD5692	Phase 3
0.65	Remote Similarity	NPD4252	Approved
0.6486	Remote Similarity	NPD4696	Approved
0.6486	Remote Similarity	NPD5285	Approved
0.6486	Remote Similarity	NPD4700	Approved
0.6486	Remote Similarity	NPD5286	Approved
0.6481	Remote Similarity	NPD6001	Approved
0.6476	Remote Similarity	NPD5208	Approved
0.6475	Remote Similarity	NPD8294	Approved
0.6475	Remote Similarity	NPD8377	Approved
0.6465	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD8035	Phase 2
0.6449	Remote Similarity	NPD5694	Approved
0.6449	Remote Similarity	NPD8034	Phase 2
0.6446	Remote Similarity	NPD6335	Approved
0.6442	Remote Similarity	NPD6098	Approved
0.6434	Remote Similarity	NPD8338	Approved
0.6429	Remote Similarity	NPD5223	Approved
0.6423	Remote Similarity	NPD8296	Approved
0.6423	Remote Similarity	NPD8378	Approved
0.6423	Remote Similarity	NPD8380	Approved
0.6423	Remote Similarity	NPD8379	Approved
0.6423	Remote Similarity	NPD8335	Approved
0.6417	Remote Similarity	NPD6274	Approved
0.6408	Remote Similarity	NPD3668	Phase 3
0.6404	Remote Similarity	NPD5141	Approved
0.6396	Remote Similarity	NPD5696	Approved
0.6393	Remote Similarity	NPD7100	Approved
0.6393	Remote Similarity	NPD7101	Approved
0.6389	Remote Similarity	NPD4202	Approved
0.6373	Remote Similarity	NPD3667	Approved
0.6372	Remote Similarity	NPD4633	Approved
0.6372	Remote Similarity	NPD5225	Approved
0.6372	Remote Similarity	NPD5224	Approved
0.6372	Remote Similarity	NPD5226	Approved
0.6364	Remote Similarity	NPD7839	Suspended
0.6364	Remote Similarity	NPD6317	Approved
0.6355	Remote Similarity	NPD5207	Approved
0.6346	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5368	Approved
0.633	Remote Similarity	NPD5282	Discontinued
0.6327	Remote Similarity	NPD8039	Approved
0.6316	Remote Similarity	NPD5175	Approved
0.6316	Remote Similarity	NPD4754	Approved
0.6316	Remote Similarity	NPD5174	Approved
0.6311	Remote Similarity	NPD6314	Approved
0.6311	Remote Similarity	NPD7154	Phase 3
0.6311	Remote Similarity	NPD6313	Approved
0.6308	Remote Similarity	NPD6845	Suspended
0.6299	Remote Similarity	NPD8074	Phase 3
0.629	Remote Similarity	NPD6909	Approved
0.629	Remote Similarity	NPD6908	Approved
0.629	Remote Similarity	NPD7503	Approved
0.629	Remote Similarity	NPD6921	Approved
0.6286	Remote Similarity	NPD5279	Phase 3
0.6286	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8337	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD8336	Approved
0.625	Remote Similarity	NPD3666	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