NPASS Compound

Structure

NPC472996 OpenBabel07101718222D 44 45 0 0 1 0 0 0 0 0999 V2000 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 1.3660 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 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 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 1.7321 -1.0000 0.0000 C 0 0 1 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 20 2 0 0 0 0 8 21 1 0 0 0 0 9 32 1 0 0 0 0 10 32 1 0 0 0 0 12 39 1 0 0 0 0 13 17 2 0 0 0 0 14 18 2 0 0 0 0 15 19 2 0 0 0 0 16 22 1 0 0 0 0 16 23 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 22 1 0 0 0 0 21 34 2 0 0 0 0 21 40 1 0 0 0 0 22 41 1 0 0 0 0 23 32 1 0 0 0 0 23 35 1 0 0 0 0 24 20 1 1 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 25 27 1 0 0 0 0 25 40 1 1 0 0 0 26 28 1 0 0 0 0 26 42 1 6 0 0 0 27 33 1 1 0 0 0 27 43 1 0 0 0 0 28 33 1 6 0 0 0 28 44 1 0 0 0 0 29 36 2 0 0 0 0 29 41 1 0 0 0 0 30 37 2 0 0 0 0 30 42 1 0 0 0 0 31 38 2 0 0 0 0 31 43 1 0 0 0 0 32 39 1 0 0 0 0 33 11 1 6 0 0 0 33 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	620.32
Volume:	637.812
LogP:	2.651
LogD:	1.438
LogS:	-3.628
# Rotatable Bonds:	17
TPSA:	147.19
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.104
Synthetic Accessibility Score:	5.563
Fsp3:	0.636
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.826
MDCK Permeability:	3.826017928076908e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.656
20% Bioavailability (F20%):	0.416
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	63.57750701904297%
Volume Distribution (VD):	2.615
Pgp-substrate:	12.146722793579102%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.468
CYP2C19-substrate:	0.545
CYP2C9-inhibitor:	0.903
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.387
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.94
CYP3A4-substrate:	0.614

ADMET: Excretion

Clearance (CL):	9.262
Half-life (T1/2):	0.667

ADMET: Toxicity

hERG Blockers:	0.239
Human Hepatotoxicity (H-HT):	0.992
Drug-inuced Liver Injury (DILI):	0.811
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.141
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.14
Carcinogencity:	0.016
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC472996

Natural Product ID:	NPC472996
*Common Name:**	XHQNFXRSYGZEFY-ZVAAVLIOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XHQNFXRSYGZEFY-ZVAAVLIOSA-N
Standard InCHI:	InChI=1S/C33H48O11/c1-13-17(4)29(36)41-22(16-23(35)32(9,10)39-12)20(7)24-25(40-21(8)34)27(43-31(38)19(6)15-3)33(11)28(44-33)26(24)42-30(37)18(5)14-2/h13-15,22-28,35H,7,16H2,1-6,8-12H3/b17-13-,18-14-,19-15-/t22?,23?,24-,25+,26+,27+,28-,33+/m1/s1
SMILES:	CC=C(C)C(=O)OC1C(C(C(C2(C1O2)C)OC(=O)C(=CC)C)OC(=O)C)C(=C)C(CC(C(C)(C)OC)O)OC(=O)C(=CC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3597519
PubChem CID:	n.a.
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
NPO32699	parasenecio rubescens	Species	Asteraceae	Eukaryota	Whole Plant	n.a.	n.a.	PMID[26200396]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	IC50	=	49650.0	nM	PMID[564719]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	96610.0	nM	PMID[564719]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	56220.0	nM	PMID[564719]

☑ 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 NPC472996 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	1616
0.2-0.3	4725
0.3-0.4	8516
0.4-0.5	14926
0.5-0.6	8170
0.6-0.7	3901
0.7-0.8	597
0.8-0.85	18
0.85-0.9	5
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472997
0.9888	High Similarity	NPC469583
0.967	High Similarity	NPC472998
0.9348	High Similarity	NPC472995
0.8681	High Similarity	NPC475087
0.835	Intermediate Similarity	NPC475586
0.83	Intermediate Similarity	NPC472552
0.83	Intermediate Similarity	NPC470972
0.8252	Intermediate Similarity	NPC181994
0.8235	Intermediate Similarity	NPC470980
0.82	Intermediate Similarity	NPC472554
0.8119	Intermediate Similarity	NPC475038
0.8119	Intermediate Similarity	NPC109195
0.81	Intermediate Similarity	NPC272223
0.81	Intermediate Similarity	NPC79303
0.81	Intermediate Similarity	NPC271295
0.8077	Intermediate Similarity	NPC475263
0.8037	Intermediate Similarity	NPC477126
0.8021	Intermediate Similarity	NPC3952
0.7981	Intermediate Similarity	NPC474716
0.7981	Intermediate Similarity	NPC473586
0.7981	Intermediate Similarity	NPC469558
0.7938	Intermediate Similarity	NPC91251
0.7938	Intermediate Similarity	NPC122057
0.7921	Intermediate Similarity	NPC38855
0.7909	Intermediate Similarity	NPC124676
0.7909	Intermediate Similarity	NPC146280
0.79	Intermediate Similarity	NPC475446
0.79	Intermediate Similarity	NPC199099
0.79	Intermediate Similarity	NPC311241
0.7885	Intermediate Similarity	NPC88349
0.7876	Intermediate Similarity	NPC473802
0.7864	Intermediate Similarity	NPC23584
0.7864	Intermediate Similarity	NPC61442
0.7857	Intermediate Similarity	NPC238090
0.7857	Intermediate Similarity	NPC472196
0.7857	Intermediate Similarity	NPC472195
0.7843	Intermediate Similarity	NPC11974
0.7835	Intermediate Similarity	NPC177668
0.7822	Intermediate Similarity	NPC107806
0.7822	Intermediate Similarity	NPC72647
0.7818	Intermediate Similarity	NPC10721
0.781	Intermediate Similarity	NPC471205
0.7807	Intermediate Similarity	NPC473919
0.7807	Intermediate Similarity	NPC473709
0.78	Intermediate Similarity	NPC475380
0.78	Intermediate Similarity	NPC209297
0.78	Intermediate Similarity	NPC129569
0.7788	Intermediate Similarity	NPC257017
0.7788	Intermediate Similarity	NPC162009
0.7778	Intermediate Similarity	NPC159698
0.7767	Intermediate Similarity	NPC11956
0.7757	Intermediate Similarity	NPC177047
0.7755	Intermediate Similarity	NPC158061
0.7755	Intermediate Similarity	NPC41838
0.7753	Intermediate Similarity	NPC477306
0.7745	Intermediate Similarity	NPC188968
0.7739	Intermediate Similarity	NPC471939
0.7736	Intermediate Similarity	NPC472439
0.7736	Intermediate Similarity	NPC469916
0.7732	Intermediate Similarity	NPC161560
0.7732	Intermediate Similarity	NPC133450
0.7727	Intermediate Similarity	NPC234858
0.7727	Intermediate Similarity	NPC154363
0.7727	Intermediate Similarity	NPC471127
0.7723	Intermediate Similarity	NPC473244
0.7723	Intermediate Similarity	NPC205143
0.7723	Intermediate Similarity	NPC100912
0.7714	Intermediate Similarity	NPC51719
0.77	Intermediate Similarity	NPC276110
0.7699	Intermediate Similarity	NPC52839
0.7692	Intermediate Similarity	NPC474822
0.7692	Intermediate Similarity	NPC474124
0.7692	Intermediate Similarity	NPC477314
0.7685	Intermediate Similarity	NPC470076
0.7679	Intermediate Similarity	NPC472667
0.7672	Intermediate Similarity	NPC471940
0.766	Intermediate Similarity	NPC231601
0.7653	Intermediate Similarity	NPC471378
0.7653	Intermediate Similarity	NPC312471
0.7642	Intermediate Similarity	NPC67321
0.7642	Intermediate Similarity	NPC187435
0.7642	Intermediate Similarity	NPC122816
0.764	Intermediate Similarity	NPC477305
0.764	Intermediate Similarity	NPC477312
0.764	Intermediate Similarity	NPC477316
0.764	Intermediate Similarity	NPC477308
0.764	Intermediate Similarity	NPC477304
0.764	Intermediate Similarity	NPC477315
0.764	Intermediate Similarity	NPC477309
0.764	Intermediate Similarity	NPC477313
0.7636	Intermediate Similarity	NPC73314
0.7636	Intermediate Similarity	NPC472400
0.7636	Intermediate Similarity	NPC43213
0.7636	Intermediate Similarity	NPC216665
0.7634	Intermediate Similarity	NPC474894
0.7629	Intermediate Similarity	NPC470260
0.7629	Intermediate Similarity	NPC75443
0.7624	Intermediate Similarity	NPC211810
0.7624	Intermediate Similarity	NPC476315
0.7624	Intermediate Similarity	NPC471765
0.7624	Intermediate Similarity	NPC279621
0.7624	Intermediate Similarity	NPC221801
0.7624	Intermediate Similarity	NPC284194
0.7619	Intermediate Similarity	NPC474550
0.7619	Intermediate Similarity	NPC473577
0.7619	Intermediate Similarity	NPC473543
0.7619	Intermediate Similarity	NPC475585
0.7619	Intermediate Similarity	NPC194941
0.7615	Intermediate Similarity	NPC317460
0.7615	Intermediate Similarity	NPC328074
0.7615	Intermediate Similarity	NPC321272
0.7615	Intermediate Similarity	NPC470025
0.7615	Intermediate Similarity	NPC317687
0.7611	Intermediate Similarity	NPC472759
0.7611	Intermediate Similarity	NPC157252
0.7611	Intermediate Similarity	NPC329080
0.7611	Intermediate Similarity	NPC471126
0.7611	Intermediate Similarity	NPC145182
0.7611	Intermediate Similarity	NPC471128
0.7611	Intermediate Similarity	NPC475885
0.7604	Intermediate Similarity	NPC311163
0.76	Intermediate Similarity	NPC256368
0.76	Intermediate Similarity	NPC161998
0.76	Intermediate Similarity	NPC105375
0.76	Intermediate Similarity	NPC105490
0.76	Intermediate Similarity	NPC182826
0.76	Intermediate Similarity	NPC140277
0.7596	Intermediate Similarity	NPC258547
0.7596	Intermediate Similarity	NPC283343
0.7596	Intermediate Similarity	NPC273668
0.7596	Intermediate Similarity	NPC474709
0.7596	Intermediate Similarity	NPC476471
0.7596	Intermediate Similarity	NPC475344
0.7593	Intermediate Similarity	NPC472214
0.7593	Intermediate Similarity	NPC316708
0.7593	Intermediate Similarity	NPC472215
0.7579	Intermediate Similarity	NPC78673
0.7579	Intermediate Similarity	NPC160517
0.7579	Intermediate Similarity	NPC186155
0.7573	Intermediate Similarity	NPC16601
0.7573	Intermediate Similarity	NPC469551
0.7573	Intermediate Similarity	NPC47024
0.757	Intermediate Similarity	NPC94377
0.757	Intermediate Similarity	NPC50124
0.757	Intermediate Similarity	NPC88701
0.757	Intermediate Similarity	NPC38948
0.7568	Intermediate Similarity	NPC471816
0.7568	Intermediate Similarity	NPC470075
0.7551	Intermediate Similarity	NPC291875
0.7549	Intermediate Similarity	NPC475332
0.7549	Intermediate Similarity	NPC120299
0.7549	Intermediate Similarity	NPC474395
0.7549	Intermediate Similarity	NPC120446
0.7547	Intermediate Similarity	NPC475290
0.7547	Intermediate Similarity	NPC111952
0.7547	Intermediate Similarity	NPC471206
0.7545	Intermediate Similarity	NPC470027
0.7545	Intermediate Similarity	NPC472757
0.7528	Intermediate Similarity	NPC477311
0.7528	Intermediate Similarity	NPC477303
0.7526	Intermediate Similarity	NPC44538
0.7525	Intermediate Similarity	NPC476720
0.7525	Intermediate Similarity	NPC36954
0.7525	Intermediate Similarity	NPC14961
0.7525	Intermediate Similarity	NPC270013
0.7524	Intermediate Similarity	NPC473523
0.7524	Intermediate Similarity	NPC281378
0.7524	Intermediate Similarity	NPC471938
0.7523	Intermediate Similarity	NPC17791
0.7523	Intermediate Similarity	NPC317107
0.7523	Intermediate Similarity	NPC469655
0.7523	Intermediate Similarity	NPC470026
0.7523	Intermediate Similarity	NPC474846
0.7523	Intermediate Similarity	NPC469656
0.7522	Intermediate Similarity	NPC77689
0.7522	Intermediate Similarity	NPC473839
0.7522	Intermediate Similarity	NPC156745
0.7522	Intermediate Similarity	NPC22628
0.7522	Intermediate Similarity	NPC255081
0.7522	Intermediate Similarity	NPC471108
0.7522	Intermediate Similarity	NPC5991
0.7522	Intermediate Similarity	NPC275696
0.7522	Intermediate Similarity	NPC470186
0.7522	Intermediate Similarity	NPC5989
0.7522	Intermediate Similarity	NPC236918
0.7522	Intermediate Similarity	NPC473636
0.7522	Intermediate Similarity	NPC211093
0.75	Intermediate Similarity	NPC212486
0.75	Intermediate Similarity	NPC206618
0.75	Intermediate Similarity	NPC296822
0.75	Intermediate Similarity	NPC471494
0.75	Intermediate Similarity	NPC110022
0.75	Intermediate Similarity	NPC7349
0.75	Intermediate Similarity	NPC40728
0.75	Intermediate Similarity	NPC299590
0.75	Intermediate Similarity	NPC298595
0.75	Intermediate Similarity	NPC476300
0.75	Intermediate Similarity	NPC475617
0.75	Intermediate Similarity	NPC473160

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 NPC472996 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	2092
0.2-0.3	3729
0.3-0.4	2109
0.4-0.5	752
0.5-0.6	221
0.6-0.7	40
0.7-0.8	4
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8763	High Similarity	NPD5344	Discontinued
0.8404	Intermediate Similarity	NPD7838	Discovery
0.8283	Intermediate Similarity	NPD6648	Approved
0.8021	Intermediate Similarity	NPD6698	Approved
0.8021	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD4225	Approved
0.713	Intermediate Similarity	NPD7328	Approved
0.713	Intermediate Similarity	NPD7327	Approved
0.7	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7638	Approved
0.6949	Remote Similarity	NPD8379	Approved
0.6949	Remote Similarity	NPD8296	Approved
0.6949	Remote Similarity	NPD8033	Approved
0.6949	Remote Similarity	NPD8378	Approved
0.6949	Remote Similarity	NPD8335	Approved
0.6949	Remote Similarity	NPD8380	Approved
0.6937	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6686	Approved
0.6916	Remote Similarity	NPD7640	Approved
0.6916	Remote Similarity	NPD7639	Approved
0.6897	Remote Similarity	NPD7115	Discovery
0.6893	Remote Similarity	NPD7983	Approved
0.6864	Remote Similarity	NPD8377	Approved
0.6864	Remote Similarity	NPD8294	Approved
0.6814	Remote Similarity	NPD6371	Approved
0.6796	Remote Similarity	NPD3168	Discontinued
0.6739	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7503	Approved
0.6609	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7507	Approved
0.656	Remote Similarity	NPD7319	Approved
0.6529	Remote Similarity	NPD8516	Approved
0.6529	Remote Similarity	NPD8517	Approved
0.6529	Remote Similarity	NPD8515	Approved
0.6529	Remote Similarity	NPD8513	Phase 3
0.6496	Remote Similarity	NPD8133	Approved
0.6486	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.641	Remote Similarity	NPD8297	Approved
0.6393	Remote Similarity	NPD6921	Approved
0.6374	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7524	Approved
0.6339	Remote Similarity	NPD7632	Discontinued
0.6316	Remote Similarity	NPD5357	Phase 1
0.6311	Remote Similarity	NPD6319	Approved
0.6293	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7829	Approved
0.629	Remote Similarity	NPD7830	Approved
0.6271	Remote Similarity	NPD6053	Discontinued
0.627	Remote Similarity	NPD8074	Phase 3
0.6226	Remote Similarity	NPD1695	Approved
0.6218	Remote Similarity	NPD4632	Approved
0.6204	Remote Similarity	NPD5779	Approved
0.6204	Remote Similarity	NPD5778	Approved
0.619	Remote Similarity	NPD8273	Phase 1
0.616	Remote Similarity	NPD7642	Approved
0.616	Remote Similarity	NPD8328	Phase 3
0.6147	Remote Similarity	NPD7748	Approved
0.6126	Remote Similarity	NPD7902	Approved
0.6111	Remote Similarity	NPD7637	Suspended
0.6087	Remote Similarity	NPD371	Approved
0.6068	Remote Similarity	NPD6899	Approved
0.6068	Remote Similarity	NPD6881	Approved
0.6058	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.605	Remote Similarity	NPD6650	Approved
0.605	Remote Similarity	NPD8130	Phase 1
0.605	Remote Similarity	NPD6649	Approved
0.6038	Remote Similarity	NPD4250	Approved
0.6038	Remote Similarity	NPD4251	Approved
0.6036	Remote Similarity	NPD7839	Suspended
0.6034	Remote Similarity	NPD6402	Approved
0.6034	Remote Similarity	NPD7128	Approved
0.6034	Remote Similarity	NPD5739	Approved
0.6034	Remote Similarity	NPD6008	Approved
0.6034	Remote Similarity	NPD6675	Approved
0.6032	Remote Similarity	NPD7604	Phase 2
0.6017	Remote Similarity	NPD6373	Approved
0.6017	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1694	Approved
0.6	Remote Similarity	NPD6882	Approved
0.5984	Remote Similarity	NPD7492	Approved
0.5983	Remote Similarity	NPD5697	Approved
0.5983	Remote Similarity	NPD6412	Phase 2
0.598	Remote Similarity	NPD4819	Approved
0.598	Remote Similarity	NPD4820	Approved
0.598	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.598	Remote Similarity	NPD4822	Approved
0.598	Remote Similarity	NPD4821	Approved
0.5969	Remote Similarity	NPD7736	Approved
0.5966	Remote Similarity	NPD7102	Approved
0.5966	Remote Similarity	NPD7290	Approved
0.5966	Remote Similarity	NPD6883	Approved
0.5965	Remote Similarity	NPD4159	Approved
0.5963	Remote Similarity	NPD7515	Phase 2
0.5962	Remote Similarity	NPD7154	Phase 3
0.5962	Remote Similarity	NPD6110	Phase 1
0.5962	Remote Similarity	NPD6695	Phase 3
0.5946	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD4249	Approved
0.5938	Remote Similarity	NPD6616	Approved
0.5935	Remote Similarity	NPD6009	Approved
0.5935	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD7320	Approved
0.592	Remote Similarity	NPD6054	Approved
0.5917	Remote Similarity	NPD6869	Approved
0.5917	Remote Similarity	NPD6617	Approved
0.5917	Remote Similarity	NPD6847	Approved
0.5891	Remote Similarity	NPD7078	Approved
0.5891	Remote Similarity	NPD8293	Discontinued
0.5888	Remote Similarity	NPD7750	Discontinued
0.5882	Remote Similarity	NPD6013	Approved
0.5882	Remote Similarity	NPD6012	Approved
0.5882	Remote Similarity	NPD6014	Approved
0.5873	Remote Similarity	NPD5983	Phase 2
0.5872	Remote Similarity	NPD5785	Approved
0.5865	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7900	Approved
0.5852	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD5701	Approved
0.5827	Remote Similarity	NPD6370	Approved
0.5818	Remote Similarity	NPD8035	Phase 2
0.5818	Remote Similarity	NPD8034	Phase 2
0.5814	Remote Similarity	NPD8451	Approved
0.5814	Remote Similarity	NPD6336	Discontinued
0.5806	Remote Similarity	NPD7505	Discontinued
0.5798	Remote Similarity	NPD6011	Approved
0.5794	Remote Similarity	NPD6059	Approved
0.5784	Remote Similarity	NPD4271	Approved
0.5784	Remote Similarity	NPD4268	Approved
0.578	Remote Similarity	NPD6101	Approved
0.578	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD8448	Approved
0.5766	Remote Similarity	NPD6399	Phase 3
0.576	Remote Similarity	NPD7641	Discontinued
0.5752	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD6016	Approved
0.5748	Remote Similarity	NPD6015	Approved
0.5748	Remote Similarity	NPD8444	Approved
0.5714	Remote Similarity	NPD5282	Discontinued
0.5714	Remote Similarity	NPD7260	Phase 2
0.5704	Remote Similarity	NPD8415	Approved
0.5703	Remote Similarity	NPD5988	Approved
0.5702	Remote Similarity	NPD6421	Discontinued
0.5702	Remote Similarity	NPD6084	Phase 2
0.5702	Remote Similarity	NPD4634	Approved
0.5702	Remote Similarity	NPD6083	Phase 2
0.5701	Remote Similarity	NPD5363	Approved
0.5676	Remote Similarity	NPD6411	Approved
0.5673	Remote Similarity	NPD6930	Phase 2
0.5673	Remote Similarity	NPD7525	Registered
0.5673	Remote Similarity	NPD6931	Approved
0.566	Remote Similarity	NPD5362	Discontinued
0.5656	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD5211	Phase 2
0.5639	Remote Similarity	NPD8391	Approved
0.5639	Remote Similarity	NPD8392	Approved
0.5639	Remote Similarity	NPD8390	Approved
0.5636	Remote Similarity	NPD6051	Approved
0.5615	Remote Similarity	NPD8299	Approved
0.5615	Remote Similarity	NPD8342	Approved
0.5615	Remote Similarity	NPD8341	Approved
0.5615	Remote Similarity	NPD8340	Approved
0.5603	Remote Similarity	NPD5285	Approved
0.5603	Remote Similarity	NPD4696	Approved
0.5603	Remote Similarity	NPD5286	Approved
0.56	Remote Similarity	NPD6274	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